johncarlosbaez, (edited )
@johncarlosbaez@mathstodon.xyz avatar

Suppose you were trying to invent a bright orange powder that could easily dye clothes and be hard to wash off. Using your knowledge of quantum mechanics you'd design this symmetrical molecule where an electron's wavefunction can vibrate back and forth along a chain of carbons at the frequency of green light. Absorbing green light makes it look orange! And this molecule doesn't dissolve in water.

Yes: you'd invent turmeric!

Or more precisely 'curcurmin', the molecule that gives turmeric its special properties.

The black atoms are carbons, the white are hydrogens and the red are oxygens.

Read on and check out what pure curcurmin looks like.

(1/n)

xavier,

@johncarlosbaez I'm curious about this idea of an electron's wavefunction vibrating along the chain at visible light frequency. If I look up the length of C-C and C=C bonds, in simple hydrocarbons they're roughly 150pm each. So if I look at tumeric, this adds up to ~2nm for the length of the molecule, which is quite far from the ~500nm wavelength of yellow light. Do you happen to know what I'm misunderstanding here?

johncarlosbaez, (edited )
@johncarlosbaez@mathstodon.xyz avatar

@xavier - what matters is not the length of the chain of carbons but the difference in energy levels between two states of an electron that's delocalized and spread over the whole chain. We can convert this energy difference E into a frequency ν by

ν = ℏ/E

where ℏ is Planck's constant, and the molecule will easily emit and absorb light of that frequency.

Here's a bit more detail:

https://www.youtube.com/watch?v=zAQz5J3Tpgs

xavier,

@johncarlosbaez Thanks for the explanation! This rings a bell, reminds me of some stuff I learnt in physics/chemistry at uni, though clearly I forgot most of it. The video's interesting, though most of it goes over my head 😅

gilesgoat,
@gilesgoat@toot.wales avatar

@johncarlosbaez It's VERY hard to wash OFF but "lore" says that it's quite sensitive to alcohol and UV light. They say the way to "wash it off" is soak it in alcohol and expose to sunlight. Makes GREAT curries anyway :)

deewani,
@deewani@mastodon.social avatar

@johncarlosbaez So neat! Uses in India go way back. Refrigeration was not a thing, meat/poultry marinated in yogurt & turmeric b/c antimicrobial properties…. more here: https://www.ncbi.nlm.nih.gov/books/NBK92752/#_ch13_sec2_. Oxi-clean or oxygen bleach is your best friend to get stains out, or rubbing the stain with dishsoap like Dawn if you can’t wash it immediately.

deewani,
@deewani@mastodon.social avatar

@johncarlosbaez Much of the middle income and higher Indian diaspora build “haldi kitchens” (haldi=turmeric) in their garages, or outdoors because of the staining properties. I refuse to do this. Stains can be avoided with care and frequent handwashing. And by taking care of any stains from cooking splashes immediately. OFC choice of countertop material, etc all impt. Don’t get me started on poor ventilation and cooking….

copsewood,

@johncarlosbaez

I had a similar effect from white lilly pollen when this accidentally brushed against my white shirt when I was handling an arrangement of these flowers and the pollen coloured an area of the shirt strongly orange. Thankfully it came out completely in the wash as it was the first time I'd worn the shirt.

ersatzmaus,

@johncarlosbaez Ha. I got as far as your first sentence and thought "turmeric". So much yellow. Clothes. Skin. Pots and pans. Worktops.

johncarlosbaez,
@johncarlosbaez@mathstodon.xyz avatar

@ersatzmaus - it's an evil substance in my opinion. I don't think the flavor is worth it! But my wife disagrees, and she does most of the cooking. In general her use of spices is very nice. But turmeric is a nuisance.

ersatzmaus,

@johncarlosbaez I really only use it for the colour, mostly for reasons of tradition.

Some dishes are Supposed To Be Yellow™.

And then only in small amounts.

Coriander/Cumin/Pepper/Chilli are the core spices for me.

iChas,

@johncarlosbaez @ersatzmaus
Having been brought up on Indian food, the oh-so-familiar turmeric was taken for granted until neuroscientists started wondering why there was so little Alzheimers amongst India’s elderly.

johncarlosbaez,
@johncarlosbaez@mathstodon.xyz avatar

@iChas -

"Can turmeric help treat dementia?

There is currently no real evidence that supports turmeric being used to prevent or treat Alzheimer’s disease. "

https://www.alzheimers.org.uk/about-dementia/risk-factors-and-prevention/turmeric-and-dementia

flarion,

@johncarlosbaez that's amazing!thx!

canusfeminacanis,

@johncarlosbaez

Nope. I'd make an azo dye of the most hideous orange that would permanently stain my lab coat.

Organic chemistry at work. 😉

Turmeric can be removed with a washing additive. Azo dye can't.

johncarlosbaez,
@johncarlosbaez@mathstodon.xyz avatar

@canusfeminacanis - okay, you're an actual chemist! So I should have added an extra requirement: you can cook with it.

canusfeminacanis,

@johncarlosbaez

Nope, but I was one of three students who didn't leave an explosion on the lab ceiling. 😆
Sometimes successes are the better teachers.

Still have the lab coat with the orange dye, though.

That said, if you'd specified 'must be able to cook with it, I would have understood turmeric to be THE answer. 😉

mc,

@johncarlosbaez lol does this work with any color you want? just stick enough Cs between the aromatic groups?

johncarlosbaez,
@johncarlosbaez@mathstodon.xyz avatar

@mc - basically yes! But the aromatic groups appear to be optional. The reason tomatoes are red is 'lycopene':

(1/3)

johncarlosbaez,
@johncarlosbaez@mathstodon.xyz avatar

@mc - and the reason carrots are orange is beta-carotene:

johncarlosbaez,
@johncarlosbaez@mathstodon.xyz avatar

@mc - I got into this when I saw a bunch of autumn leaves again in Washington DC, and realized it's all due to quantum delocalization of electrons! I wrote about it here:

(3/3)

https://johncarlosbaez.wordpress.com/2021/11/28/anthocyanins/

b3nb3n,

@johncarlosbaez @mc is it somehow possible to guess the color from the length of the chain of carbons?

johncarlosbaez,
@johncarlosbaez@mathstodon.xyz avatar

@b3nb3n @mc - yes if you're smart enough, but I'm not. The frequency of vibration will be lower for longer carbon chains, just like for a violin string, but I bet the side-groups attached to the chains also affect the frequency - like the oxygens in curcurmin. So you should get the cleanest patterns for very simple chains like

C-C=C-C=C-C=C-C

(with appropriate hydrogens attached).

CompadredeOgum,
@CompadredeOgum@ursal.zone avatar

@johncarlosbaez @b3nb3n @mc lycopene is red and is the longest chain you showed. Shouldn't it be the opposite? Longer = lower frequency?

samloonie,

@CompadredeOgum @johncarlosbaez @b3nb3n @mc Red is the lower frequency, longer wavelength.

johncarlosbaez,
@johncarlosbaez@mathstodon.xyz avatar

@samloonie @CompadredeOgum @b3nb3n @mc - red is longer frequency, lower wavelength but a chemical looks red if it absorbs a lot of green light. I think I'd need to see a bunch of extremely similar carbon chain molecules that form conjugated systems, before I could feel sure about the patterns.

https://en.wikipedia.org/wiki/Conjugated_system

jameshowell,
@jameshowell@emacs.ch avatar

@johncarlosbaez @b3nb3n @mc I vividly remember the moment in grad school twenty-odd years ago when it suddenly hit me that conjugated carbon-carbon double bonds are a hallmark of dyes "" (as well as fluorescent molecules ""). Because they happen to have of just the right energies to absorb visible ! (Or ultraviolet photons, and then emit visible photons.)

One of my many post-undergrad "WHY oh WHY DIDN'T THEY MENTION THIS IN ?!" moments.

yours_truly,
@yours_truly@troet.cafe avatar

@johncarlosbaez @mc

Thank you for sharing, very interesting Topic.

> "Anthocyanins have been used in organic solar cells because of their ability to convert light energy into electrical energy."
https://en.wikipedia.org/wiki/Anthocyanin

> "The anthocyanins have other tasks in the plants: They should

absorb the sun's short-wave UV light in the shell and transfer the radiant energy to the plant as heat. This prevents damage to the proteins in the cell and the DNA in the cell nuclei."
https://de.wikipedia.org/wiki/Anthocyane

johncarlosbaez, (edited )
@johncarlosbaez@mathstodon.xyz avatar

Ain't it pretty? People extract curcumin from turmeric to use as a food coloring in curry powders, mustards, butters, cheeses, and prepared foods. It's also used in dietary supplements due to its unproven and dubious health benefits.

It doesn't dissolve well in water, but it does in alcohol. If you dissolve some curcurmin in vodka and shine a black light on it, you'll see it's fluorescent! That is: it absorbs the high-energy ultraviolet photons and emits lower-energy green photons... the same kind of light it usually likes to absorb. Due to the principle of reciprocity, if a substance is good at absorbing some frequency of light, it's also good at emitting that frequency.

Let's see that fluorescence! Check out my next post.

(2/n)

bracken,

@johncarlosbaez can it stop oil?

johncarlosbaez,
@johncarlosbaez@mathstodon.xyz avatar

@bracken - I don't know what that means.

bracken,

@johncarlosbaez When you say "Suppose you were trying to invent a bright orange powder that could easily dye clothes and be hard to wash off" it sounds like you're preparing a protest relevant to current events in the UK.

happydisciple,
@happydisciple@mendeddrum.org avatar

@johncarlosbaez In Dutch turmeric is called either “kurkuma” (after the Sanskrit name, I guess the source of both the name of the genus and of “curcumin”), “geelwortel” (= yellowroot), or kunyit/koenjit (from Indonesian)

johncarlosbaez,
@johncarlosbaez@mathstodon.xyz avatar

@happydisciple - nice! I was wondering where that word 'curcumin' came from, and I was confused by 'cucurbits'.

https://en.wikipedia.org/wiki/Cucurbita

johncarlosbaez, (edited )
@johncarlosbaez@mathstodon.xyz avatar

Here's curcumin dissolved in a hydrocarbon called xylene with ultraviolet light shining on it! It's fluorescent. You can also dissolve it in ethanol, e.g. vodka.

Curcurmin also makes a good pH detector: if you mix it with a base it turns red. This video by @compoundchem illustrates it:

https://www.youtube.com/watch?v=PsVtME5o69I

(3/n, n = 3)

mc,

@johncarlosbaez @compoundchem this explains many culinary experiences I had, amazing

johncarlosbaez,
@johncarlosbaez@mathstodon.xyz avatar

@mc - I've spent a lot of time trying to wash turmeric out of my clothes; I should have been using vodka.

pascaline,
@pascaline@mastodon.nl avatar

@johncarlosbaez
I loved this entire post, thanks! Fun to read and informative 😊 As a teacher, I can appreciate that 😀

@compoundchem

johncarlosbaez,
@johncarlosbaez@mathstodon.xyz avatar

@pascaline - thanks very much! That's what I aim for: informative yet fun.

alcea,

@johncarlosbaez @compoundchem
Shudder

#Chemistry my mortal #nemesis

varx,
@varx@cybersecurity.theater avatar

@johncarlosbaez Aha, that explains why when I was washing a turmeric-covered spoon the other day, I saw a brief glimpse of red! I think the water sitting in our faucet can end up a bit basic at times, based on past observations. (Or possibly something else is going on with the chlorine in the water?)

ramoonus,

@johncarlosbaez @compoundchem xylene is toxic and absorbs UV light

alopex,
@alopex@furries.club avatar

@johncarlosbaez Huh! This booze I picked up recently has a VERY strong and persistent yellow color. It lists saffron as the top billing flavor/ingredient, but I always wondered how much of the color was really from the turmeric.

Did not think to try shining UV light on it before drinking it all!

Back side of the Apologue bottle from the previous image. Focus is on ingredients, including saffron, green cardamom, coriander, turmeric, kalonjig, golden raisin, orange peel, lemon grass, curry leaf, organic cane sugar and neutral grain spirit.

johncarlosbaez,
@johncarlosbaez@mathstodon.xyz avatar

@alopex - interesting! Saffron sounds a lot more high-class than turmeric. Next time you get one, break out the black lights for your party!

metaweta,

@johncarlosbaez @compoundchem And tonic water also fluoresces thanks to the quinine!

ThamizhKudimagan,

@johncarlosbaez
In Tamil (the oldest language that is still widely spoken), turmeric is called 'manjal' ( மஞ்சள் ) and the color yellow is also called 'manjal'!

johncarlosbaez,
@johncarlosbaez@mathstodon.xyz avatar

@ThamizhKudimagan - cool! I guess turmeric was one of the most important yellow things for some culture.

CarolynStearns,

@johncarlosbaez fascinating

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