Tag Archives: sucrose

Brilliant Bee Chemistry!

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20th May is World Bee Day, the aim of which is to raise awareness of the importance of bees and beekeeping. So, hey, let’s do that!

I’m helped this month by my horticulturist* dad who, while working in a public garden recently, discovered this honeybee swarm in a honeysuckle. (Me: “what sort of tree is that?” Dad: “a winter flowering Honeysuckle lonicera. It’s a shrub, not a tree!” Yes, despite his tireless efforts I’m still pretty clueless about plants.)

Now, Dad knows what he’s doing in such situations. He immediately called the professionals. One does not mess around with (or ignore) a swarm of bees – one finds a beekeeper, stat. Obviously bees can sting, but they’re also endangered and they need to be collected to protect them. Should you find yourself in such a situation, you can find someone local via the British Beekeepers Association website.

That out of the way, aren’t they gorgeous? A swarm like this is a natural phenomenon, that happens when new queen bees are born and raised in the colony. Worker bees stop feeding the old queen – because a laying queen is too heavy to fly – and then in time she leaves with a swarm. They cluster somewhere, as you see in the photo, while scout bees go looking for a new location to settle. Bees in swarms only have the honey or nectar in their stomachs to keep them going, so they’ll starve if they don’t find a new home, and nectar, quickly.

This is all fascinating, of course, but what does it have to do with chemistry? Well, quite a bit, because bees are brilliant chemists. Really!

Ethyl oleate is an ester and an important chemical for bees (image source)

Firstly, despite what DreamWorks might have taught us, bees don’t have vocal cords, and they don’t sound like Jerry Seinfeld. A lot of their communication is chemical-based (actually, it turns out this is a topic of hot debate in bee circles, but since this is a chemistry blog, I’m not doing waggle dances. No, not even if you ask nicely).

As you might imagine, there are multiple chemicals involved, and I won’t go into all of them. Many are esters, which are known for their sweet, fruity smells, and which are also (at least, the longer-chain ones) the building blocks of fats.

One such chemical is ethyl oleate which plants produce and which, interestingly, we humans also make in our bodies when we drink alcohol. Forager bees gather ethyl oleate and carry it in their stomachs, and they then feed it to worker bees. It has the effect of keeping those workers in a nurse bee state and prevents them from maturing into forager bees too early. But, as forager bees die off, less ethyl oleate is available, and this “tells” the nurse bees to mature more quickly – so the colony makes more foragers. Clever, eh?

In this situation, ethyl oleate is acting as a pheromone, in other words, a substance that triggers a social response in members of the same species. Another example is Nasonov’s pheromone, which is a mixture of chemicals including geraniol (think fresh, “green” smell), nerolic acid, geranic acid (an isomer of nerolic acid) and citral (smells of lemon).

The white gland at the top of the honeybee’s abdomen releases pheromones which entice the swarm to an empty hive (image source)

An interesting aside: geranic acid has been investigated as an antiseptic material. It can penetrate skin, and has been shown to help the delivery of transdermal antibiotics, which are being investigated partly as a solution to the problem of antibiotic resistance. Nature is, as always, amazing.

Anyway, worker bees (which, again contrary to DreamWorks’ narrative, are female) release Nasonov’s pheromone to orient returning forager bees (also female) back to the colony. They do this by raising up their abdomens and fanning their wings. Beekeepers can use synthetic Nasonov pheromone, sometimes mixed with a “queen bee pheromone” to attract honeybee swarms to an unoccupied hive or swarm-catching box.

As my Dad chatted to the beekeepers (partly on my insistence – I was on the other end of my phone texting questions and demanding photos) one substance they were particularly keen to mention was “the alarm pheromone,” which “smells of bananas.”

Ooh, interesting, I thought. Turns out, this is isoamyl acetate, which is another ester. In fact, depending on your chemistry teacher’s enthusiasm for esters, you might even have made it in school – it forms when acetic acid (the vinegary one) is combined with 3-methylbutan-1-ol (isoamyl alcohol).

Never eat a banana by a bee.

Isoamyl acetate is used to give foods a banana flavour and scent. But, funnily enough, actual bananas you buy in the shops today don’t contain very much of it, the isoamyl acetate-rich ones having been wiped out by a fungal plague in the 1990s. This has lead to the peculiar situation of banana-flavoured foods tasting more like bananas than… well… bananas.

Modern bananas can still be upset bees, though. There are numerous stories of unwary individuals who walked too close to hives while eating a banana and been attacked. So, top tip: if you’re going on a picnic, leave the bananas (and banana-flavoured sweets, milkshakes etc) at home.

The reason is that banana-scented isoamyl acetate is released when honeybees sting. They don’t do this lightly, of course, since they can’t pull out the barbed stinger afterwards, and that means the bee has to leave part of its digestive tract, muscles and nerves embedded in your skin. It’s death for the bee, but the act of stinging releases the pheromone, which signals other bees to attack, attack, attack.

One bee sting might not deter a large predator, but several stings will. Multiple bee stings can trigger a lethal anaphylactic reaction, known allergy or not. So although utilising their stingers causes the death of a few (almost certainly infertile) bees, the rest of the colony (including the fertile individuals) is more likely to survive. From an evolutionary perspective it’s worth it – genes survive to be passed on.

Isoamyl acetate

Isoamyl acetate is an ester that smells of bananas, and is an alarm pheremone for bees (image source)

Moving on, I obviously can’t write a whole blog post about bees and not mention honey! We take it for granted, but it’s amazingly complicated. It contains at least 181 different substances, and nothing human food scientists have been able to synthesise quite compares.

In terms of sugars, it’s mostly glucose and fructose. Now, I’ve written about sugars extensively before, so I won’t explain them yet again, but I will just reiterate my favourite soap-box point: your body ultimately doesn’t distinguish between “processed” sugars in foods and the sugars in honey. In fact, one might legitimately argue that honey is massively processed, just, you know, by bees. So, you want to cut down on your sugar intake for health reasons? Sorry, but honey needs to go, too.

Honey is actually a supersaturated solution. In very simple terms, this means there’s an excess of sugar dissolved in a small amount of water. One substance which bees use to achieve this bit of clever chemistry is the enzyme, invertase, which they produce in their salivary glands. Nectar contains sucrose (“table sugar”) and, after the bees collect nectar, invertase helps to break it down into the smaller molecules of glucose and fructose.

“Set” honey is honey that’s been crystallised in a controlled way.

That’s only the beginning, though. There are lots of other enzymes involved. Amylase breaks down another sugar, amylose, into glucose. And glucose oxidase breaks down glucose and helps to stabilise the honey’s pH. One of the molecules produced in the reaction with glucose oxidase produces is hydrogen peroxide, which yet another enzyme, catalase, further breaks down into water and oxygen.

Bees regurgitate and re-drink nectar (yes, I suggest you don’t overthink it) over a period of time, which both allows the sugar chemistry to happen and also reduces the water content. When it’s about one-fifth water, the honey is deposited in the honeycomb, and the bees fan it with their wings to speed up the evaporation process even further. They stop when it’s down to about one-sixth water.

As I said a moment ago, honey is a supersaturated solution, and that means it’s prone to crystallising. This isn’t necessarily bad, in fact, “set” honey (my personal favourite) is honey which has been crystallised in a controlled way, so as to produce fine crystals and a creamy (rather than grainy) product.

The formation of a new honeycomb.

The potential problem with crystallisation is that once the sugar crystals fall out of solution, the remaining liquid has a higher-than-ideal percentage of water. This can allow microorganisms to grow. In particular, yeasts can take hold, leading to fermentation. Honey left on the comb in the hive tends not to crystallise, but once it’s collected and stored, there’s a greater chance that some particle of something or other will get in there and trigger the process. It helps to store it somewhere above room temperature. And honey is naturally hygroscopic, which means it absorbs water. So store it somewhere dry. In short, never put honey in the fridge.

Speaking of yeast and heat, heating changes honey and makes it darker in colour, thanks to the Maillard reaction. Commercial honey is often pasteurized to kill any yeast, which improves its shelf life and produces a smoother product. Also, because honey is naturally slightly acidic (around pH 4), over time the amino acids within in start to break down and this also leads to a darkening of the colour.

One more important safety concern: honey, even when pasteurized, can contain bacteria that produce toxins in a baby’s intestines and lead to infant botulism. So, never give children under one honey. It’s not a risk for older children (and adults) thanks to their more mature digestive systems.

T

Back to Dad’s bees! They were collected in a transport box by two local experts, Sharon and Ian. The bees march into the box two-by-two, wafting Nazonov’s pheromone to signal that this is home. From there, they were safely transferred to a new, wooden hive.

There’s only one way to finish this post, I think, and that’s with one of my all-time favourite Granny Weatherwax moments:

‘Your bees,’ she went on, ‘is your mead, your wax, your bee gum, your honey. A wonderful thing is your bee. Ruled by a queen, too,’ she added, with a touch of approval.

‘Don’t they sting you?’ said Esk, standing back a little. Bees boiled out of the comb and overflowed the rough wooden sides of the box.

‘Hardly ever,’ said Granny. ‘You wanted magic. Watch.’

Happy World Bee Day, everyone and, as always, GNU Terry Pratchett.

* Dad was unsure about the label “horticulturist” but I pointed out that the definition is an expert in garden cultivation and management, particularly someone’s who’s paid for their work. All of which he is. He replied wryly that, “x is an unknown quantity, and a spurt is a long drip.” Love you, Dad x 😄

If you’re studying chemistry, have you got your Pocket Chemist yet? Why not grab one? It’s a hugely useful tool, and by buying one you’ll be supporting this site – it’s win-win! If you happen to know a chemist, it would make a brilliant stocking-filler! As would a set of chemistry word magnets!

Like the Chronicle Flask’s Facebook page for regular updates, or follow @chronicleflask on Twitter. Content is © Kat Day 2021. You may share or link to anything here, but you must reference this site if you do. If you enjoy reading my blog, and especially if you’re using information you’ve found here to write a piece for which you will be paid, please consider buying me a coffee through Ko-fi using the button below.
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Want something non-sciency to distract you from, well, everything? Why not check out my fiction blog: the fiction phial.

 

Lovely lollipops: the chemistry of sugary things

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20th July is National Lollipop Day!

Today, July 20th, is apparently national lollipop day in the United States, and general news is… *waves hands* so it seems like a good excuse to write something with lots of pictures of brightly coloured sweets, right? Plus, sugar!

The idea of putting something sugary on a stick to hold and eat is an ancient one. The very earliest humans probably used sticks to collect honey from beehives. Later, the Chinese, Egyptians and people from the Middle East dipped fruits and nuts in honey and used sticks to make them easier to eat.

In the 17th century, boiled sugar sweets were made in England and, again, sticks inserted to make eating easier. This may be where the name “lollipop” originates, since “lolly” is a dialect word for tongue. Later, in the American Civil War era (early 1860s), some sources say hard candy was put on the tips of pencils for children. In 1931 an American named George Smith started making hard candies on sticks, and trademarked the name lollipop — but he reportedly took the name from a racehorse named “Lolly Pop”.

Table sugar is sucrose

Enough history, let’s get to the chemistry! Lollipops are made of sugar, with added colours and flavours. I’ve talked about sugar before, and it’s always worth remembering that we tend to use the word rather loosely in everyday speech.

There’s more than one type of sugar: in particular, the three that are probably most familiar are glucose, fructose and sucrose. Glucose is a simple sugar, and the one you might remember from photosynthesis and respiration equations. It’s essential for life, and you quickly run into serious trouble if your blood glucose levels drop too low (just ask a diabetic).

Like glucose, fructose is a monosaccharide (the simplest form of sugar), and is often called “fruit sugar” because, guess what, it’s common in fruits. Sucrose is what we know as “table sugar” and is a disaccharide, made up of a unit of glucose joined to a unit of fructose. In the body, sucrose is broken up into glucose and fructose.

Rock candy is made from sucrose but, unlike in most lollipops and hard candy, the sugar is allowed to form large crystals

The primary ingredient in lollipops is usually sucrose, which can be persuaded (more in a minute) to set nicely to produce a hard, shiny surface. However, commercial lollipops often also include corn syrup, or glucose syrup, which contains oligosaccharides: larger sugar molecules made from a number of simple sugar molecules joined together. Typically, as the name “glucose syrup” might suggest, these molecules contain units of glucose.

It’s worth mentioning here that corn syrup/glucose syrup isn’t the same as “high fructose corn syrup” or HFCS, in which the glucose molecules have been converted into fructose. This product is cheap, sweet and commercially easy to use, but it’s also controversial. Excessive consumption has been linked to obesity and non-alcoholic fatty liver disease, although the actual evidence is weak: a systematic review in 2014 concluded that there was little evidence it was worse than other forms of sugar. It’s really a problem of quantity: it’s easy and cheap for food manufacturers to throw HFCS into foods and drinks, and of course it tastes delicious, so as a consequence consumers end up eating too much of the stuff. In short: more water and fruit, less cake and fizzy drinks.

But having done the obligatory “eat healthily” thing, one lollipop isn’t going to hurt, is it? So back to that…

Fudge, perhaps surprisingly, contains the crystalline form of sugar

When it cools, sugar forms two different types of solid: crystalline and glassy amorphous (sometimes described as ‘amorphous solid’). Now, you might imagine that sugar as a crystalline solid is found in hard sweets/candies, but, no — it mostly turns up in soft things like fudge and fondant, which contain lots of very tiny crystals, giving an ever-so slightly granular texture. (An exception is rock candy, where the sugar is encouraged to form large crystals.)

The glassy amorphous form of sugar, on the other hand, can be literally like glass: hard, brittle, and transparent. In fact, “sugar glass” has in the past been used to make windows, bottles and so on for special effects in film and television, because it’s much less likely to cause injury than “real” glass. However, it’s very fragile and hygroscopic (meaning it absorbs water, causing it to soften over time) so these days it’s largely been replaced by synthetic resins.

Honey can be used as an inhibitor, to prevent crystallisation

The glassy amorphous form of sugar is achieved by starting with a 50% sugar solution which also contains an inhibitor, to prevent crystals forming spontaneously. Common inhibitors are the corn syrup I mentioned earlier, or cream of tartar (potassium bitartrate), honey or butter.

Exactly which you use depends on the recipe, but they all do essentially the same thing, namely, get in the way of the glucose molecules and prevent them ordering themselves into a regular (crystalline) structure. The mixture is heated to a high temperature (about 155 oC) until almost all the water evaporates — the final candy will only have about 1-2% water — and then cooled until glass transition occurs.

At the glass transition point, the sugar mixture becomes solid.

This is the clever bit, and only happens if crystallisation is inhibited (else crystals form instead). Glass transition happens around 100-150 oC below the melting point of the pure substance. For example, the melting point of pure sucrose is 186 oC, but it undergoes glass transition at around 60 oC.

Glass transition is a reversible change, which we might (if I didn’t generally dislike the concept) call a physical change. It’s a change of phase, where the sugar mixture changes from liquid to solid, but it’s different from crystallisation, because instead of the molecules becoming more ordered, they simply ‘freeze’ in their random, liquid positions. (It is, for the record, annoyingly difficult to show this in diagram form.)

Amorphous solid structures are sometimes called “supercooled liquids”. This isn’t wrong, but personally I think it’s unhelpful (and can lead to nonsense about glass flowing very slowly over time). Once cooled and set, glass, whether window glass or sugar glass, is absolutely not a liquid; it’s a solid.

Of course, to make lollipops, all sorts of colours and flavours are added to the mixture as well, and sometimes more than one mixture is used to create intricate, layered effects. There are even medicinal lollipops which contain, for example, the powerful painkiller fentanyl — the idea being that the patient can administer the dose gradually as needed.

Which brings me to the end. Happy National Lollipop Day! My favourites are Chupa Chups — if you’ve enjoyed this, how about popping over to Ko-fi so I can stock up? And if you’ve been eating sweets, do remember to clean your teeth!

If you’re studying from home, have you got your Pocket Chemist yet? Why not grab one? It’s a hugely useful tool, and by buying one you’ll be supporting this site – it’s win-win!

Like the Chronicle Flask’s Facebook page for regular updates, or follow @chronicleflask on Twitter. Content is © Kat Day 2020. You may share or link to anything here, but you must reference this site if you do. If you enjoy reading my blog, and especially if you’re using information you’ve found here to write a piece for which you will be paid, please consider buying me a coffee through Ko-fi using the button below.
Buy Me a Coffee at ko-fi.com

Want something non-sciency to distract you from, well, everything? Why not check out my fiction blog: the fiction phial.

A tale of chemistry, biochemistry, physics and astronomy – and shiny, silver balls

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A new school term has started here, and for me this year that’s meant more chemistry experiments – hurrah!

Okay, actually round-bottomed flasks

The other day it was time for the famous Tollens’ reaction. For those that don’t know, this involves a mixture of silver nitrate, sodium hydroxide and ammonia (which has to be freshly made every time as it doesn’t keep). Combine this concoction with an aldehyde in a glass container and warm it up a bit and it forms a beautiful silver layer on the glass. Check out my lovely silver balls!

This reaction is handy for chemists because the silver mirror only appears with aldehydes and not with other, similar molecules (such as ketones). It works because aldehydes are readily oxidised or, looking at it the other way round, the silver ions (Ag+) are readily reduced by the aldehyde to form silver metal (Ag) – check out this Compound Interest graphic for a bit more detail.

But this is not just the story of an interesting little experiment for chemists. No, this is a story of chemistry, biochemistry, physics, astronomy, and artisan glass bauble producers. Ready? Let’s get started!

Bernhard Tollens (click for link to image source)

The reaction is named after Bernhard Tollens, a German chemist who was born in the mid-19th century. It’s one of those odd situations where everyone – well, everyone who’s studied A level Chemistry anyway – knows the name, but hardly anyone seems to have any idea who the person was.

Tollens went to school in Hamburg, Germany, and his science teacher was Karl Möbius. No, not the Möbius strip inventor (that was August Möbius): Karl Möbius was a zoologist and a pioneer in the field of ecology. He must have inspired the young Tollens to pursue a scientific career, because after he graduated Tollens first completed an apprenticeship at a pharmacy before going on to study chemistry at Friedrich Wöhler’s laboratory in Göttingen. If Wöhler’s name seems familiar it’s because he was the co-discoverer of  beryllium and silicon – without which the electronics I’m using to write this article probably wouldn’t exist.

After he obtained his PhD Tollens worked at a bronze factory, but it wasn’t long before he left to begin working with none other than Emil Erlenmeyer – yes, he of the Erlenmeyer flask, otherwise known as… the conical flask. (I’ve finally managed to get around to mentioning the piece of glassware from which this blog takes its name!)

It seems though that Tollens had itchy feet, as he didn’t stay with Erlenmeyer for long, either. He worked in Paris and Portugal before eventually returning to Göttingen in 1872 to work on carbohydrates, going on to discover the structures of several sugars.

Table sugar is sucrose, which doesn’t produce a silver mirror with Tollens’ reagent

As readers of this blog will know, the term “sugar” often gets horribly misused by, well, almost everyone. It’s a broad term which very generally refers to carbon-based molecules containing groups of O-H and C=O atoms. Most significant to this story are the sugars called monosaccharides and disaccharides. The two most famous monosaccharides are fructose, or “fruit sugar”, and glucose. On the other hand sucrose, or “table sugar”, is a disaccharide.

All of the monosaccharides will produce a positive result with Tollens’ reagent (even when their structures don’t appear to contain an aldehyde group – this gets a bit complicated but check out this link if you’re interested). However, sucrose does not. Which means that Tollens’ reagent is quick and easy test that can be used to distinguish between glucose and sucrose.

Laboratory Dewar flask with silver mirror surface

And it’s not just useful for identifying sugars. Tollens’ reagent, or a variant of it, can also be used to create a high-quality mirror surface. Until the 1900s, if you wanted to make a mirror you had to apply a thin foil of an alloy – called “tain” – to the back of a piece of glass. It’s difficult to get a really good finish with this method, especially if you’re trying to create a mirror on anything other than a perfectly flat surface. If you wanted a mirrored flask, say to reduce heat radiation, this was tricky. Plus it required quite a lot of silver, which was expensive and made the finished item quite heavy.

Which was why the German chemist Justus von Liebig (yep, the one behind the Liebig condenser) developed a process for depositing a thin layer of pure silver on glass in 1835. After some tweaking and refining this was perfected into a method which bears a lot of resemblance to the Tollens’ reaction: a diamminesilver(I) solution is mixed with glucose and sprayed onto the surface of the glass, where the silver ions are reduced to elemental silver. This process ticked a lot of boxes: not only did it produce a high-quality finish, but it also used such a tiny quantity of silver that it was really cheap.

And it turned out to be useful for more than just laboratory glassware. The German astronomer Carl August von Steinheil and French doctor Leon Foucault soon began to use it to make telescope mirrors: for the first time astronomers had cheap, lightweight mirrors that reflected far more light than their old mirrors had ever done.

People also noticed how pretty the effect was: German artisans began to make Christmas tree decorations by pouring silver nitrate into glass spheres, followed by ammonia and finally a glucose solution – producing beautiful silver baubles which were exported all over the world, including to Britain.

These days, silvering is done by vacuum deposition, which produces an even more perfect surface, but you just can’t beat the magic of watching the inside of a test tube or a flask turning into a beautiful, shiny mirror.

Speaking of which, according to @MaChemGuy on Twitter, this is the perfect, foolproof, silver mirror method:
° Place 5 cm³ 0.1 mol dm⁻³ AgNO₃(aq) in a test tube.
° Add concentrated NH₃ dropwise untill the precipitate dissolves. (About 3 drops.)
° Add a spatula of glucose and dissolve.
° Plunge test-tube into freshly boiled water.

Silver nitrate stains the skin – wear gloves!

One word of warning: be careful with the silver nitrate and wear gloves. Else, like me, you might end up with brown stains on your hands that are still there three days later…

Like the Chronicle Flask’s Facebook page for regular updates, or follow @chronicleflask on Twitter. All content is © Kat Day 2018. You may share or link to anything here, but you must reference this site if you do.

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Spectacular Strawberry Science!

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Garden strawberries

Yay! It’s June! Do you know what that means, Chronicle Flask readers? Football? What do you mean, football? Who cares about that? (I jest – check out this excellent post from Compound Interest).

No, I mean it’s strawberry season in the U.K.! That means there will be much strawberry eating, because the supermarkets are full of very reasonably-priced punnets. There will also be strawberry picking, as we tramp along rows selecting the very juiciest fruits (and eating… well, just a few – it’s part of the fun, right?).

Is there any nicer fruit than these little bundles of red deliciousness? Surely not. (Although I do also appreciate a ripe blackberry.)

And as if their lovely taste weren’t enough, there’s loads of brilliant strawberry science, too!

This is mainly (well, sort of, mostly, some of the time) a chemistry blog, but the botany and history aspects of strawberries are really interesting too. The woodland strawberry (Fragaria vesca) was the first to be cultivated in the early 17th century, although strawberries have of course been around a lot longer than that. The word strawberry is thought to come from ‘streabariye’ – a term used by the Benedictine monk Aelfric in CE 995.

Woodland strawberries

Woodland strawberries, though, are small and round: very different from the large, tapering, fruits we tend to see in shops today (their botanical name is Fragaria × ananassa – the ‘ananassa’ bit meaning pineapple, referring to their sweet scent and flavour.

The strawberries we’re most familiar with were actually bred from two other varieties. That means that modern strawberries are, technically, a genetically modified organism. But no need to worry: practically every plant we eat today is.

Of course, almost everyone’s heard that strawberries are not, strictly, a berry. It’s true; technically strawberries are what’s known as an “aggregate accessory” fruit, which means that they’re formed from the receptacle (the thick bit of the stem where flowers emerge) that holds the ovaries, rather than from the ovaries themselves. But it gets weirder. Those things on the outside that look like seeds? Not seeds. No, each one is actually an ovary, with a seed inside it. Basically strawberries are plant genitalia. There’s something to share with Grandma over a nice cup of tea and a scone.

Anyway, that’s enough botany. Bring on the chemistry! Let’s start with the bright red colour. As with most fruits, that colour comes from anthocyanins – water-soluble molecules which are odourless, moderately astringent, and brightly-coloured. They’re formed from the reaction of, similar-sounding, molecules called anthocyanidins with sugars. The main anthocyanin in strawberries is callistephin, otherwise known as pelargonidin-3-O-glucoside. It’s also found in the skin of certain grapes.

Anthocyanins are fun for chemists because they change colour with pH. It’s these molecules which are behind the famous red-cabbage indicator. Which means, yes, you can make strawberry indicator! I had a go myself, the results are below…

Strawberry juice acts as an indicator: pinky-purplish in an alkaline solution, bright orange in an acid.

As you can see, the strawberry juice is pinky-purplish in the alkaline solution (sodium hydrogen carbonate, aka baking soda, about pH 9), and bright orange in the acid (vinegar, aka acetic acid, about pH 3). Next time you find a couple of mushy strawberries that don’t look so tasty, don’t throw them away – try some kitchen chemistry instead!

Peonidin-3-O-glucoside is the anthocyanin which gives strawberries their red colour. This is the form found at acidic pHs

The reason we see this colour-changing behaviour is that the anthocyanin pigment gains an -OH group at alkaline pHs, and loses it at acidic pHs (as in the diagram here).

This small change is enough to alter the wavelengths of light absorbed by the compound, so we see different colours. The more green light that’s absorbed, the more pink/purple the solution appears. The more blue light that’s absorbed, the more orange/yellow we see.

Interestingly, anthocyanins behave slightly differently to most other pH indicators, which usually acquire a proton (H+) at low pH, and lose one at high pH.

Moving on from colour, what about the famous strawberry smell and flavour? That comes from furaneol, which is sometimes called strawberry furanone or, less romantically, DMHF. It’s the same compound which gives pineapples their scent (hence that whole Latin ananassa thing I mentioned earlier). The concentration of furaneol increases as the strawberry ripens, which is why they smell stronger.

Along with menthol and vanillin, furaneol is one of the most widely-used compounds in the flavour industry. Pure furaneol is added to strawberry-scented beauty products to give them their scent, but only in small amounts – at high concentrations it has a strong caramel-like odour which, I’m told, can actually smell quite unpleasant.

As strawberries ripen their sugar content increases, they get redder, and they produce more scent

As strawberries ripen their sugar content (a mixture of fructose, glucose and sucrose) also changes, increasing from about 5% to 9% by weight. This change is driven by auxin hormones such as indole-3-acetic acid. At the same time, acidity – largely from citric acid – decreases.

Those who’ve been paying attention might be putting a few things together at this point: as the strawberry ripens, it becomes less acidic, which helps to shift its colour from more green-yellow-orange towards those delicious-looking purpleish-reds. It’s also producing more furaneol, making it smell yummy, and its sugar content is increasing, making it lovely and sweet. Why is all this happening? Because the strawberry wants (as much as a plant can want) to be eaten, but only once it’s ripe – because that’s how its seeds get dispersed. Ripening is all about making the fruit more appealing – redder, sweeter, and nicer-smelling – to things that will eat it. Nature’s clever, eh?

There we have it: some spectacular strawberry science! As a final note, as soon as I started writing this I (naturally) found lots of other blogs about strawberries and summer berries in general. They’re all fascinating. If you want to read more, check out…

Like the Chronicle Flask’s Facebook page for regular updates, or follow @chronicleflask on Twitter. All content is © Kat Day 2018. You may share or link to anything here, but you must reference this site if you do.

If you enjoy reading my blog, please consider buying me a coffee (I might spend it on an extra punnet of strawberries, mind you) through Ko-fi using the button below.
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Is it possible to give up sugar completely?

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It’s January, a month that’s traditionally marked by cold weather, large credit-card bills and, of course, an awful lot of highly questionable health stuff. Juicing, detox, supplements… it’s all good fun. Until someone gets hurt.

"Refined" sugar is almost entirely made up of a molecule called sucrose.

“Refined” sugar is almost entirely made up of a molecule called sucrose.

One substance that regularly gets a bashing is sugar, particularly so-called “refined” sugar. We’re told it’s toxic (it’s not), it’s more addictive than cocaine (it isn’t) and we should definitely all be trying to give it up.

Now, before I go any further with this, a word about healthy eating. I’m not a dietician. I don’t even claim to be a nutritionist (although I could, if I wanted). However, I think I’m on fairly safe ground if I say that we should all be striving for a healthy, balanced diet. That is, a diet containing a broad range of foods, plenty of fruits and vegetables, healthy amounts of protein and some good fats.

A lot of people have diets that fall short of this ideal. Cutting back on foods which contain a lot of added sugar (cakes, chocolate, fizzy drinks, etc) and eating more vegetables and fruits is a good, and sensible, course of action.

The problem is that bit of common-sense advice doesn’t sell books or make an interesting TV show. It’s all a bit boring and, worse, it’s freely available. Compelling entertainment needs to be more exciting, more dramatic, more… extreme.

Which brings us to ITV’s Sugar Free Farm.

Page 81 of the current issue of Radio Times tells us that the celebrities face a "completely sugar-free regime".

Page 81 of the current issue of Radio Times tells us that the celebrities face a “completely sugar-free regime”.

This is actually the second series of this show, which first aired last year. According to the 7-13th January 2017 issue of the Radio Times:

“Seven celebrities who admit to terrible diets succumb to a few weeks of hard farm labour and a completely sugar-free regime (so no white carbs or fruit, let alone chocolate).”

Hm. Now, I’ve written about sugar more than once before, but to save clicking back and forth, here’s another quick summary:

Sugar is not one thing. The chemistry of sugars is quite complicated, but a human being trying to understand the food they eat probably needs to be aware of three main types, namely: glucose, fructose and sucrose.

180px-Glucose_chain_structure

glucose

Glucose is the sugar that all your cells need. Not having enough glucose in your bloodstream is called hypoglycaemia, and the result is seizure, coma and ultimately death. This isn’t a risk for healthy people without pre-existing conditions (like diabetes, for example) because evolution has put some clever safety-nets in place. First, our bodies are extremely efficient at carrying out the necessary chemistry to turn the molecules we eat into the molecules we need. Should that fail, our bodies are very good at storing nutrients to use in times when our diet doesn’t supply them. If you don’t eat glucose, your body will break down other foods to produce it, then it’ll start on your glycogen stores, move on to fat stores, and eventually start breaking down protein (i.e. the stuff in your muscles). This means that unless you stop eating completely for a fairly long period of time, you’ll survive.

Still, I think it’s important to emphasise the point: glucose is essential for life. The suggestion that this substance is “toxic” and thus should be completely eliminated from our diets is really, when you think about it, a bit odd.

Sucrose ("refined sugar") is a unit of glucose joined to a unit of fructose

Sucrose (“refined sugar”) is a unit of glucose joined to a unit of fructose

Ah but, I hear some people saying, no one is saying that glucose is toxic! They’re talking about refined sugar!

Fine. So what’s “refined” sugar? In simple terms, it’s pure sucrose. And sucrose is just a molecule made from a unit of glucose stuck to a unit of fructose. As I said, our bodies are really good at breaking up the molecules we eat into the molecules we need: our cells can’t use sucrose for energy, so all that happens is that it more or less instantly gets broken up into glucose and fructose.

Refined sugar is, basically, half glucose and half fructose, and it’s no more dangerous or “toxic” than either of those substances. And while I’m here, “natural” sugar options are little different: honey, for example, contains similar ratios of fructose and glucose.

200px-Skeletal_Structure_of_D-Fructose

Fructose

Allrighty then, what’s fructose? Fructose is another simple sugar, and it’s the one that plants produce. For that reason it’s sometimes called “fruit sugar”.

Our cells can’t use fructose for energy, either. But, same thing again: if you eat it your body will still use it. In this case, your liver does the heavy lifting; changing fructose into glucose and other substances, some of which are fats. On the one hand, this is a slower process so you don’t get the blood sugar spike with fructose that you get with glucose. On the other, some of the fructose you eat inevitably ends up being converted into fat.

As I mentioned, fructose is the sugar in plants. It’s found in almost all plant-based foods. For example, the USDA food composition database tells us that 100 g of carrots contains about 0.6 g of fructose. Perhaps surprisingly, broccoli contains slightly more: about 0.7 g per 100 g. Iceberg lettuce contains even more, at 1 g per 100 g, whereas green peas contain a mere 0.4 g.

Even a really small glass of fruit juice contains about 150 g.

Even a small serving of fruit juice usually contains at least 150 g.

None of this comes close to fruit. Apples contain about 6 g of fructose per 100 g, grapes 4 g and bananas 5 g. Dried fruit, as you’d expect, has considerably higher amounts by weight – because the water’s gone. Juices have similar amounts of fructose per unit of weight but, of course, you tend to drink a lot more than 100 g of juice at a time.

Now we understand why “Sugar Free Farm” has banned fruit. But this is why I have a problem with the title: you CAN’T eat an entirely “sugar-free” diet, unless all you eat is meat, fish, eggs and dairy products like cream and butter (but not milk, which contains lots of another sugar: lactose). This would be a far from healthy diet, seriously lacking in fibre as well as a host of vitamins and minerals (even “phase 1” or the “induction” period of the controversial Atkins diet isn’t quite this extreme).

The show hasn’t aired yet, and I admit I didn’t watch it last year, so I don’t know if that’s what they’re doing. But I seriously doubt it – it would be unethical and irresponsible. Plus, the words “white carbs” in the listings blurb make me suspicious. Why specify “white”? Are whole grains included? And what about pulses? Whole grain foods might be relatively low in fructose and glucose before you put them in your mouth, but as soon as saliva hits them the starch they contain is broken down into…. glucose. By the time you swallow that chewed-up food, it contains sugar.

In summary, Sugar Free Farm is almost certainly not sugar free. What they appear to have set up is a place where sugars are restricted and foods with added sugar are banned, and then mixed that with lots of outdoor activities (the celebrities are also expected to work on the farm).

Most people would lose weight following such a regime, because it’s likely that calories in are going to be lower than calories out. It’s a simple calorie deficit.

give-up-sugarWhat bothers me is that the show might go on to conclude that we should all “give up” sugar to lose weight – and some people might misinterpret that and end up embarking on an unbalanced, unhealthy and ultimately unsustainable diet – when in fact the results are simply due to calorie deficit.

There’s no need to try to give up sugar. Cut down, yes, but you can eat some sweet foods and still manage a calorie deficit. In fact you probably should: fruit in particular has lots of nutrients, including fibre. Besides, such a diet will probably be a lot more sustainable in the long term.

Unfortunately, “Eat Fewer Calories And Do Some Exercise Farm” doesn’t have quite the same ring, does it?

EDIT, 11th Jan 2017

Well, the first episode aired last night. No, the diet is not “zero sugar”. It’s very low in sugar, yes, but there are sugars. They used milk (contains lactose), ate wholemeal bread, brown rice and oats (all of which are broken down into glucose) and ate a variety of vegetables which, as I mentioned above, all contain small amounts of sugar. In fact, on their very first morning they eat a strange granola mixture made with sweet potato. The USDA food database tells me that sweet potato contains about 0.4 g of fructose, 0.5 g of glucose, 3.3 g of maltose AND 1.4 g of sucrose per 100 g. Yep. Sucrose. The stuff in “refined” sugar.

There was much talk of “detox” and “detoxing” from sugar. Sigh. That’s not a thing. Most worryingly of all, poor Peter Davison (he was “my” Doctor, you know) was carted off in an ambulance on the second day, suffering with dizzy spells. Everyone immediately started talking about how dreadful it was that “sugar” had caused this. There was only one, in passing, comment shown suggesting that perhaps the 65-year-old might have something else wrong with him. In fact, it turned out that he had labyrinthitis, an inner-ear condition. It’s usually viral. It’s not caused by “sugar withdrawal”. I’m sure they’ll make that clear in the next episode, right?

Speaking of which, the celebrities are on Sugar Free Farm for 15 days. A safe rate of weight loss is generally considered to be 0.5-1 kg (or 1-2 lb) a week. So they should lose about 2 kg, or 4 lb, on the outside. A snippet was shown at the end of the program in which Alison Hammond said she was “pleased” she’d lost 8 lbs. Whether that was after two weeks or a shorter period of time wasn’t clear, but either way, it’s a lot. It suggests that her diet is/was too low in calories, particularly considering all the extra physical activity.  Perhaps some of her so-called “sugar withdrawal” symptoms were actually simply due to the fact that she wasn’t consuming enough to keep up with her energy needs?

That aside, the diet they followed did seem to be fairly balanced, with plenty of vegetables and adequate healthy fats and protein. They had all been eating huge quantities of sugary foods beforehand, and cutting down is no bad thing. I’m just skeptical about exactly how much of the bad, and indeed the good, can be pinned on sugar.

Still, it made good telly I suppose.

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No, ketchup does not cause cancer

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ketchup and coke

Do these things really cause breast cancer? (Spoiler: no)

Less than two days into the new year, and I’d already found what might well be one of the silliest health headlines of the year. What is it I hear you ask? Well, it was in a national newspaper on New Years Day, and it was this:

“Sugar found in ketchup and Coke linked to breast cancer”

This, to borrow a favourite line from an online greetings card company, had me rolling my eyes so hard I could practically see my brain. Why? Because even without reading any further, I knew immediately that it was the equivalent of saying, “too much of thing found in most stuff might cause cancer!”

But let’s not be one of the 70% of users that only read the headline, let’s dig a little further. The newspaper article, which in fairness isn’t too bad – it’s just a bit of a silly headline, alludes to work carried out the University of Texas’ MD Anderson Cancer Centre. If you click on the link I’ve added back there, you’ll see that MD Anderson’s headline was:

“Sugar in Western diets increases risk for breast cancer tumors and metastasis”

Note, they just say ‘sugar’, not sugar in two apparently randomly-selected foodstuffs. The researchers divided mice into four groups, fed some a diet high in sucrose (more commonly called table sugar – in other words, the stuff in the sugar bowl) and compared them to others fed a low-sugar, ‘starch-controlled’ diet. They found that the high-sugar diet lead to increased tumour growth, particularly in mammary glands.

I’ve covered forms of sugar before but still, here’s a quick reminder before we go any further: this is a molecule of sucrose:

Saccharose2

Sucrose

Sucrose is made of two ‘bits’ joined together: one unit of fructose and one unit of glucose.

157px-Alpha-D-Glucopyranose

Glucose

These two molecules are what chemists call isomers. They contain the same number and type of atoms, just joined up differently. They’re both sugars in and of themselves. Glucose is used directly by cells in your body for energy. Fructose, on the other hand, is trickier. It has a lower glycemic index than glucose, in other words, it doesn’t raise your blood sugar as rapidly as glucose, but this doesn’t mean it’s healthier. It’s metabolised almost exclusively in the liver and, long story short, invariably ends up being converted into, and stored as, fat.

179px-Beta-D-Fructofuranose

Fructose

Fruit is high in fructose, and fructose tastes very sweet to us (sweeter than either glucose or sucrose). This is nature’s way of telling us, and other animals that might eat the fruit, that it’s high in nutrients. From the plant’s point of view, it’s an incentive to eat the fruit and, ahem, spread the seeds around.

Humans have, of course messed around with this perfectly sensible survival mechanism by stuffing all kinds of easily-available and not particularly nutrient-rich foods with fructose, and herein lies the problem. Co-author of the paper that started all this, Lorenzo Cohen, Ph.D., professor of Palliative, Rehabilitation, and Integrative Medicine, said “we determined that it was specifically fructose, in table sugar and high-fructose corn syrup […] which was responsible for facilitating lung metastasis and 12-HETE production in breast tumors.” Notice that he mentions fructose in table sugar; this is because, once you eat sucrose, it breaks down into units of glucose and fructose.

The article goes on to suggest that sugar-sweetened beverages are a significant problem, so was the newspaper wrong to pick on Coke? It’s a popular drink after all, and a standard can of Coca-Cola contains approximately 35 grams of sugar (which might come from either sucrose or high fructose corn syrup mainly depending on where you buy it). The guidance for adults is no more than 30 grams of sugar per day, so a single can of regular Coca-Cola would take you over that limit, and it’s very easy to drink two or even three cans without giving it a second thought.

sugar

Soft drinks and fruit juice both contain a lot of sugar

However, the same goes for pretty much any non-diet soft drink.  Pepsi, for example, has a similar amount. Lemonade can be even more sugary, with some drinks hitting 40 grams per 330 ml can. Ginger beer might well be the worst; there are 53 grams per 330 ml in Old Jamaica Ginger beer for example. Fruit juice is no better, with many juices containing 35 g of sugar per 330 ml, although at least fruit juice might contain some other nutrients such as vitamin C.

So really, I’d say it’s a bit unfair to single out Coke in a headline like this.

What about the ketchup (note they didn’t pick a specific brand here, just generic ‘ketchup’)?

Well, ketchup IS high in sugar. It contains about 24 grams of sugar per 100 grams. But hang on, 100 grams of ketchup is quite a lot. A more realistic serving size of a tablespoon is only about 15 grams, which works out at about 3.5 grams of sugar. Still quite a lot, but probably a drop in the ocean compared to all the sugar in cake, bread, drinks, fruit juice, breakfast cereals and the tubs of Roses and Quality Street you scoffed over Christmas. Unless you make a habit of drinking ketchup by the bottle (apparently some people do) this is frankly a ridiculous foodstuff to pick on.

I imagine that someone did a quick search for ‘foods that contain fructose’ and picked Coke because, well, everyone knows that Coke’s bad, right? So that sounds credible. And ketchup because we all sort of suspect it’s probably not that healthy, but it hasn’t been the subject of a health scare recently so that makes it stand out. Great clickbait, bad science.

mouse

Mice are not people

Plus, let’s be absolutely clear, the study was in mice. Mice are not people. While a study that shows an effect in mice is an interesting start, and may well be good reason to conduct more studies, quite possibly in humans, it’s not proof that this mechanism exists in humans. Humans have, after all, evolved to eat a very different diet to mice. There might well be a link, but this doesn’t prove it, and even if a link does exist we certainly can’t say anything about the significance or size of it from this research.

I’m not a dietician, but I’m going to go out on a (fairly sturdy) limb here and say that cutting back on sugar will not do you any harm and is likely to be a jolly good thing. Let’s also be clear that sugar in fruit juice, agave, honey etc is still sugar and is no healthier than table sugar. Eating too much of the sweet stuff is almost definitely bad for your waistline and, as we all learned as children, bad for your teeth too – something which is often overlooked but really shouldn’t be, poor dental health having been linked to other serious health problems including diabetes and heart disease.

ketchup on bread

Maybe cut back on the fried ketchup sandwiches

But, and here’s my big problem with the newspaper’s headline, none of this means that Coke and ketchup directly cause breast cancer which is how, I fear, some people will interpret it. Cut out sugary fizzy drinks by all means, and perhaps ditch the ketchup sandwiches (especially fried ones), but please don’t worry that the occasional dollop of red sauce is going to kill you. I’m pretty certain it won’t.

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A small edit was made on 6th January to clarify that pure fructose isn’t used as an ingredient in Coke, but rather high fructose corn syrup.

 

 

Sugar that’s not sugar?

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A couple of days ago I was catching up with last Sunday’s Dragon’s Den. For the non-Brits out there, this is a show in which entrepreneurs pitch business ideas to a panel of ‘dragons’ – i.e. successful business people – to get an investment of money and, perhaps more importantly, expertise and contacts. It’s a great show that’s been running for quite a few years now and has resulted in a number of products and brands becoming household names – in the UK anyway.

LinusGorpeDragonsDen

Linus Gorpe on BBC’s Dragon’s Den

The last entrepreneur to pitch in the show was the founder of the Raw Chocolate Company, an interesting character called Linus Gorpe (quote: “I love life. Life is the dance for me. I play a lot. I play in the woods. I eat a lot of healthy food. I love clean living. I love women, oh I love women.” Ahem).

He was promoting his ‘raw’ chocolate products. The Dragons asked what he meant by raw: he said something about heating up apples for two hours in an oven. I don’t think anyone was much the wiser. But I’m not going to pick holes in the ideas behind raw food diets (Science Based Medicine wrote a great article on that topic a little while back, I urge you to check it out).

No, I was more bothered by this little exchange:

Deborah Meaden: “So, the sugar content when comparing it to other chocolate. Same?”
Linus: “No. I use coconut palm sugar, which is um, not refined white sugar. It’s the sugar that’s been made from-”
DM (interrupting): “That’s interesting, so it’s unrefined?”
LG: “It’s unrefined. It’s boiled. So it doesn’t raise your blood sugar levels.”

Peter Jones chimed in at this point on something else entirely, leaving me shouting pointlessly at the telly. Not least because hadn’t he just said heating food was basically bad? And now he’s talking about boiling?!

Saccharose2

Sucrose

But that’s the least of my problems with this. Firstly, what is the difference between refined sugar and unrefined sugar? As the name suggests it’s really just a question of processing. Somehow the word ‘refined’ seems to have become irrevocably linked in people’s minds with ‘horribly unhealthy’ whereas ‘raw sugar’ somehow sounds much better. In reality, in the case of cane sugar (for the sake of comparing like with like), all the ‘refined’ bit means is that any non-sugar ingredients, which mainly provide flavour and colour, have been removed and the water has been rapidly evaporated from the sugar solution to produce fine, white crystals of pure sucrose.

Raw sugar, before the refining process, is still mostly sucrose. And truly raw sugar syrup, i.e. completely unprocessed, doesn’t often work very well as an ingredient. So when people talk about ‘unrefined’ sugar, what they usually mean is ‘a bit less refined’ sugar.

Ah, I hear you say, but he didn’t say cane sugar. He said coconut palm sugar. Yes, he did. So what’s that, then?

Coconut palm sugar, or just coconut sugar, is sugar produced from the sap of the cut flower buds of the coconut palm plant. It is usually less refined than cane sugar: essentially the syrup is harvested from the plant and then simply heated to remove the excess water. It’s a pretty simple process.

But does that make it any healthier? What does it actually contain?

179px-Beta-D-Fructofuranose

Fructose

157px-Alpha-D-Glucopyranose

Glucose

Well, coconut palm sugar is, guess what, about 80% sucrose. The remaining 20% is made up of a mixture of glucose and fructose. Both of which are also sugars. In fact, if you have a look at the images I’ve inserted here, they’re very similar molecules. Chemists describe them as isomers; they have the same number and types of atoms, just arranged slightly differently. If you’ve really been paying attention, you might notice that sucrose is, in fact, just a glucose molecule joined up with a fructose molecule.

When you eat sucrose, your body breaks it down into glucose and fructose. So practically, consuming any of these will have basically the same result, which is to raise your blood sugar. Pure glucose causes the biggest spike, because your body doesn’t have to do anything very much at all in the way of digestion, but just to make this absolutely clear: table sugar is not glucose. It is sucrose.

How much your blood sugar rises when you eat mostly depends on what else is in the food. A whole piece of fruit, for example, also contains a lot of fibre. That fibre slows down digestion, which means the sugar (there’s a lot of fructose in fruit) is absorbed more slowly than if you, say, swallowed a teaspoon of the same sugar on its own.

Coconut palm sugar

Coconut palm sugar

In short, refined sugar raises your blood sugar levels. But so does unrefined/raw/partially-refined/whatever-we’re-calling-it-today sugar. It was frankly flat-out incorrect of Linus to state that coconut palm sugar doesn’t raise blood sugar levels, because it does.

There is a bit of debate around how much it raises blood sugar levels. One oft-quoted study (consisting of a grand total of ten participants, and carried out by the Philippine Food and Nutrition Research Institute – incidentally the Philippines is one of the world’s largest producers of coconut palm sugar) quoted a glycemic index (GI) for coconut sugar of about 35, which would compare quite favourably with table sugar (about 58) and pure glucose (100, by definition).

On the other hand, hunt around a bit and another source pops up quoting a GI of 54 for coconut sugar. Which is… about the same as table sugar (and given the chemical make-up of coconut sugar, it’s hard to think of a good reason why they should be very different).

The truth is, there isn’t any such thing as ‘healthy’ sugar, certainly not in the way we talk about ‘healthy fats‘. If you’re going to eat products made with sugar, any sugar, you have to accept that while they may be jolly tasty (that ought to be a give-away, really) they’re treats, and should probably still be enjoyed only in moderation.

I’m sure that the Raw Chocolate Company’s products are delicious, and I’m not particularly anti-sugar. But let’s not be misleading. If someone genuinely cares, for whatever reason, about the sugar in their food, it’s important they get accurate information. Saying things like “it doesn’t raise your blood sugar” is, well, frankly a bit naughty.

The dragons know their stuff, and Deborah Meaden (who eventually invested) is a very smart lady. There’s no way she’ll allow any inaccurate, or even questionable, claims to persist in the long term, so I daresay this is the last time we’ll hear the blood sugar thing in relation to these products. But still, if he’d quoted dubious sales figures they’d have been all over it. Grrr.

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About this time last year I wrote a post about a company claiming that their agave-sweetened products are ‘sugar-free’. They’re still out there. They still say their products are sugar-free (although they are making some that are sweetened with the sweetener xylitol now, which they’ve bizarrely chosen to label ‘no added sugar’). Their products still do, in fact, contain sugar. Sigh.

The Chronicle Flask’s festive chemistry quiz!

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Tis the season to be jolly! And also for lots of blog posts and articles about the science of christmas, like this one, and this one, and this one, and even this one (which is from last year, but it’s jolly good).

But here’s the question: have you been paying attention? Well, have you? Time to find out with The Chronicle Flask’s festive quiz! I haven’t figured out how to make this interactive. You’ll have to, I don’t know, use a pen and paper or something.

Arbol_de_navidad_con_adornos_de_personajesQuestion 1)
Which scientist invented a chemical test that can be used to coat the inside of baubles with silver?
a) Bernhard Tollens
b) Karl Möbius
c) Emil Erlenmeyer

Question 2)
Reindeer eat moss which contains arachidonic acid… but why is that beneficial to them?
a) a laxative
b) an anti-freeze
c) a spider repellant

1280px-ChristmasCrackers_2Question 3)
Which chemical makes crackers and party poppers go crack?
a) gunpowder
b) silver fulminate
c) nitrogen triiodide

640px-Glass_of_champagneQuestion 4)
We all like a glass of champagne at this time of year, but what’s in the bubbles?
a) carbon dioxide
b) nitrogen
c) oxgyen

Question 5)
What’s the key ingredient in those lovely bath salts you bought for your grandma?
a) calcium carbonate
b) magnesium sulfate
c) citric acid

The Bird - 2007Question 6)
Which chemical reaction is responsible for both perfectly browned biscuits and crispy, golden turkey?
a) Maillard reaction
b) Hodge reaction
c) Caramel reaction

Question 7)
Sucrose-rodmodelWhere are you most likely to find this molecule at this time of year?
a) in a roast beef joint
b) in the wrapping paper
c) in the christmas cake

Question 8)
Let it snow, let it snow, let it snow… but which fact about (pure) water is true?
a) It glows when exposed to ultraviolet light
b) It expands as it freezes
c) It’s a good conductor of electricity

Ethanol-3D-ballsQuestion 9)
Where are you likely to find this molecule on New Year’s Eve?
a) in a champagne bottle
b) in the party poppers
c) in the ‘first foot’ coal

OperaSydney-Fuegos2006-342289398Question 10)
Who doesn’t love a firework or two on New Years Eve?  But which element is most commonly used to produce the colour green?
a) magnesium
b) sodium
c) barium

(Answers below…)

1a) Bernhard Tollens (but his science teacher was Karl Möbius).
2b) It’s a natural anti-freeze.
3b) Silver fulminate (it always surprises me how many people guess gunpowder. That would be exciting).
4a) carbon dioxide.
5b) magnesium sulfate which, funnily enough, also causes ‘hard’ water.
6a) the Maillard reaction, although Hodge did establish the mechanism.
7c) In the cake – it’s sucrose (table sugar).
8b) it expands as it freezes and is thus less dense than liquid water (which is why ice floats). We take this for granted, but most things contract (and become more dense) as they turn from liquid to solid. You should be grateful – live probably wouldn’t have evolved without this peculiar behaviour.
9a) In the champagne – it’s ethanol (or ‘alcohol’ in everyday parlance).
10c) barium – copper produces green flames too, but barium salts are more commonly used in fireworks.

So how did you do?
Less than 4: D, for deuterium. It’s heavy hydrogen and it’s used to slow things down. Enough said.
4-6: You get a C, by which I mean carbon. Have another slice of coal.
7-8: You’ve clearly been paying attention. B for boring, I mean boron.
9-10: Au-ren’t you clever? Chemistry champion!

Happy New Year everyone! 🙂

Something about sugar (free)

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Blenheim Flower Show

The Blenheim Flower Show

Last month I went to the Blenheim Flower Show. I hadn’t been before, and I wasn’t quite sure what to expect. In my head I was imagining rows and rows of flowers with a sort of maze-like path through them. I have no idea why, possibly I’ve been doing too much Wizard of Oz (this is not a euphemism).

Perhaps not surprisingly it wasn’t like that at all. In fact the flowers were confined to a couple of easily-avoidable tents, leaving me to wander around stalls selling everything from jewellery to space-saving furniture, chat to the jolly interesting chaps giving a bee-keeping demonstration and scrounge free samples from the food tent.

And it was in the food tent that I came across the Raw Chocolate Pie stall. Sounds good doesn’t it? They’ve combined some very appealing words there. Anyway, the ladies on the stall were very nice and gave me some pieces to taste, and it was indeed scrummy, and sweet. I mention this because in huge letters across the top of the stall were the words “sugar free”. Hm, I thought. They had already told me that the ‘pies’ (actually more like chocolatey lumps) were made with raw cacao beans. Now, I’m a fan of dark chocolate and I’ve tasted 90% cocoa chocolate. It’s bitter. Bitter with a capital bit. It also has a sort of powdery texture due to the low fat content, and this had neither quality.

“So,” I said conversationally, “what’s it sweetened with?”

“Agave nectar,” came the reply.

thefoodofthegodsAt this point I’d heard of agave nectar but I wasn’t really sure what it actually was, so I simply nodded and bought a bar of nut pie. I intended to bring it home and investigate it properly, but it was hot and it got a bit melty, so I was forced to eat it at lunchtime. I took a picture of the wrapper though.

See how it says “sugar free” right there at the top? They are big on this claim. It says sugar free all over the Living Food raw chocolate pie website too.

What would you imagine that means?

It’s a pertinent question. Sugar is one of those words, like ‘salt‘ and ‘alcohol‘, which has a subtly different meaning in chemistry than it does in everyday speech. For chemists these are groups of compounds, but if you read “add pinch of salt” in a recipe book you don’t wonder whether to add sodium chloride or the copper sulfate from your child’s chemistry set. Likewise, if a bottle of wine claims to be 14% alcohol you don’t ponder whether it’s safe to drink or whether you should save it for paint stripper. (Unless, that is, it’s very cheap wine indeed.)

No, in everyday speech we know that salt means sodium chloride, alcohol means ethanol and sugar means, er… sugar means…

Sucrose

Sucrose

This is where it gets a bit sticky. Because there’s more than one sugar that we eat on a regular basis. The white, or sometimes brown, stuff that people bake with and plop into their hot beverages is mainly sucrose. It’s also called ‘table sugar’, or sometimes ‘cane sugar’ or ‘beet sugar’, because those are the plants from which it’s extracted.

Raw chocolate pies haven’t been made with cane/beet sugar, so they might be able to truthfully claim to be sucrose-free. But sugar-free? We-ell…

180px-Glucose_chain_structure

Glucose

The other two sugars that we’re probably most familiar with are glucose, which is the fuel our cells use for energy during respiration, and fructose, which is found in plants and which, like glucose, can be absorbed directly into the bloodstream.

200px-Skeletal_Structure_of_D-Fructose

Fructose

So fructose is found in plants. In fact, fructose is often found in plants chemically bonded to glucose. To make…. sucrose.

So in short:
glucose + fructose = sucrose

And they’re all sugars, and we eat them all on a fairly regular basis. Our bodies break up sucrose into units of glucose and fructose during digestion, and it’s fair to say that none of them are particularly healthy if consumed in large quantities. They’re calorific, bad for your teeth, nutrient-free (other than as an energy source), and regularly eating large quantities of sugar (of any kind) puts you at a greater risk of type II diabetes.

So what’s in agave nectar? Well it comes from a plant, the agave plant, so if you’ve been paying attention that should give you a clue. Yep, it’s packed full of fructose. Which is a sugar. In fact, there are a lot of health concerns around fructose. You may have heard of high fructose corn syrup, or HFCS. This stuff is controversial, with claims that it contributes to obesity, cardiovascular disease, diabetes and non-alcoholic fatty liver disease. Other groups claim these links are unproven, and it’s no worse than any other type of sugar. These groups are mainly people that make and sell high fructose corn syrup, so draw your own conclusions.

Back to agave nectar or, more accurately, syrup. It actually has considerably more fructose than high fructose corn syrup. So bearing all that in mind, is it a healthy alternative? Er, almost certainly not.

Is it correct to call something that’s sweetened with agave ‘sugar free’?

I had a little poke around the Food Standards website. It was something of a slog, but as far as I can work out, the word ‘sugar’ in an ingredients list specifically refers to sucrose. So, you don’t have to list ‘sugar’ in the ingredients list if sucrose isn’t specifically used as an ingredient. But what about the term ‘sugar-free’?

I struggled to find a clear definition of this term on the FSA website, which was a bit annoying (see update below). The best source I can come up with is The Sugar Association, which I’m fairly sure is an American site and so the information quoted wouldn’t apply to a British producer. Still, it’s the best I’ve got, and I’d put money on the rules being similar if not quite identical. This is what they say:

‘“Sugar Free”: Less than 0.5 g sugars per reference amount and per labeled serving (or for meals and main dishes, less than 0.5 g per labeled serving). No ingredient that is a sugar or generally understood to contain sugars except as noted below(*)’ (sic)

The “as noted below” refers to sugar alcohols. These are things like xylitol, mannitol and sorbitol. They often turn up in things like chewing gum. Fructose, at the risk of stating the obvious, is not a sugar alcohol.

There was no percentage composition on the raw chocolate pie wrapper, but just from the taste I’m pretty certain it had more than 0.5 g of sugars (i.e. fructose) per serving. Nothing is that sweet without sugars, unless it also contains artificial sweeteners (which aren’t listed as an ingredient).

I did find this on the Food Standards website:

“To sell food and drink products, the label must be: […] not misleading”

Sugar-free Coke?

Sugar-free Coke?

Is calling something sweetened with a high-fructose syrup (because that’s what agave ‘nectar’ is) misleading? I’m afraid to say that, although I did very much enjoy my nut pie snack, I think it is. By the logic that seems to be being applied here, Coca Cola could use high fructose corn syrup as an sweetener and label their red non-diet bottles and cans as sugar-free, which would be patently ridiculous.

It’s a shame really, because Living Food have a nice product. They just need to get their labelling sorted out.

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Update 4th August 2014
After I wrote this I continued my quest to find a proper definition of “sugar-free”. I tried the Food Standards Agency, who sent me to Defra, who ignored me. So I went back to the FSA, who eventually sent me this link. It’s a very interesting document, clarifying and giving examples of how EU Regulation No. 1924/2006, which is all about nutrition and health claims on food, should be applied. On page 70 it says:

‘”The Regulation does […] define any product with no more than 0.5g of sugar per 100ml or per 100g as “sugar free”’

And so conversely, anything with more than 0.5 g of sugar per 100 g as NOT sugar-free. (The official definitions of sugar-free, low-sugar and no added sugar can all be found in the Annex, on page 14, of EU Regulation No. 1924/2006). What still wasn’t entirely clear was exactly what’s meant by ‘sugar’. But now I had somewhere to start. Rooting through EU Regulation No. 1924/2006 I found that it referred to Directive 90/496/EEC for definitions. And there, finally, I got my answer, in Article 1, page 4:

“‘sugars’ means all monosaccharides and disaccharides present in food, but excludes polyols”

Voilà! Fructose is a monosaccharide, and therefore if your product has more than 0.5 g of fructose per 100 g, then it cannot accurately be labelled sugar-free.

I can’t prove this is the case for the Raw Chocolate Pies, since I my testing involves tasting two samples. But if it looks like a duck, and quacks like a duck, it’s probably a very sugary duck.

The question of ‘no added sugar’ may be somewhat irrelevant, since they’re not making this claim, but I think it’s illuminating. If agave syrup has been added then “no added sugar” can’t even be used, since (from regulation (EC) No. 1924/2006):

“A claim stating that sugars have not been added to a food, and any claim likely to have the same meaning for the consumer, may only be made where the product does not contain any added mono- or disaccharides or any other food used for its sweetening properties.”

So that’s the end of the journey, really. You can only call something sugar-free if there’s no sugar in it, and that includes fructose (‘fruit sugar’), glucose and sucrose (‘table’ sugar). Foods sweetened with agave, which contains fructose, aren’t sugar-free, unless they have only the tiniest amount – less than 0.5 g per 100 g – added.