Why “Natural” isn’t always better: almond extract and cyanide

Right now the various species of Prunus are in flower all over northern California; the ornamental plums that are so popular as sidewalk decor are shedding petals everywhere, apricot blossoms are peeking out from yards, and the almond trees that crop up as renegades from the big orchards near Davis and in the central valley are covered in popcorn-y pinkish white flowers.  With constant reminders of stone fruit everywhere but none actually in season to eat, I’ve been doing a lot of baking with almonds and almond extract.

A sprinkling of wild plum blossoms (Prunus americana) on my way to lab.

Natural almond extract is not made from the edible almonds that are farmed here (Prunus dulcis), rather, it’s usually made from closely-related bitter almonds (Prunus amygdalus), and sometimes from more surprising sources, like cinnamon bark.  The chemical that we recognize so definitively as almond flavoring is benzaldehyde, and it’s found in several plants both in and out of the Prunus genus.  If you have a bottle of “natural almond extract” at home, chances are that yours, like mine, is a suspension of bitter almond oil in either glycerin or ethanol.

The taste of almonds (or apricot kernels, or sometimes cinnamon or cassava masquerading as almonds): benzaldehyde.

On to the cyanide part…and why that delicious flavor is really the plant trying to scare you off or kill you.

Gabriel Garcia Marquez once wrote poetically about the scent of bitter almonds and the fate of unrequited love as a lead-in to murder by cyanide poisoning.  And in bitter almond oil as in a tragic romance, the sweet and the toxic are inextricably entangled.  Benzaldehyde is made by the decomposition of amygdalin (named for Prunus amygdalus, and in turn responsible for the bitterness that gives bitter almonds their common name).  The other decomposition products are glucose (sweet) and hydrogen cyanide (toxic).

The bitter almond molecule amygdalin, which breaks down (left to right) into glucose, glucose, hydrogen cyanide (aka Prussic acid to the classicists), and benzaldehyde.

As with so many other useful or toxic chemicals that we get from plants, the evolutionary utility of amygdalin to the plant is for defense, specifically as a deterrent to grazers from eating the valuable seed as well as the dispensable fruit.  Inside the cells of the almond kernel, amygdalin is sequestered from the enzyme that breaks it down: amygdalin hydrolase.  Crushing, as happens when the plant is grazed upon, brings the enzyme and amygdalin together, and cyanide is produced as a result–as much as 4-9mg per almond.  If the bitter taste of amygdalin doesn’t deter the grazer, the light-headedness, weakness, and racing heart that follows as the cyanide out-competes oxygen for the grazer’s hemoglobin probably will.  It freaks me out a little to remember that, as children, my brother and I noticed that apricot kernels looked exactly like almonds, and tried a few before deciding that the resemblance stopped at the visual level and they were too nasty to keep eating (spoiler alert: we lived).

But despite the almond trees’ efforts to deter us, humans like me have decided we really love the taste of benzaldehyde, and so commercial producers have developed a range of methods to generate it in a form that won’t also kill us.  Most descriptions of bitter almond oil preparation I’ve seen (here’s an example) involve crushing the kernels, which brings the amygdalin and hydrolase together, drying the powder into a cake, macerating the cake in water, which washes away much of the water-soluble cyanide, leaving the benzaldehyde-rich oil behind, and then akali-washing the oil to remove the rest of the cyanide.  The oil that’s left is then resuspended in ethanol or glycerol.  But this is still imperfect, and some retailers of natural almond extract caution that it can still be toxic in large amounts (one estimate is that 7.5mL of bitter almond oil would be lethal).

Why bother with amygdalin at all?

This is the main issue–there’s really no reason to buy natural almond extract.  Benzaldehyde is easy to make synthetically without ever bringing it near cyanide. And ethanol suspensions of benzaldehyde are sold (more cheaply than natural almond extract) as imitation almond extract.  It’s a more strongly-flavored product, and there’s no risk of poisoning.  But as consumers, most of us assume “natural” must be better than “imitation”, and the hippie grocery store we usually shop at doesn’t even sell imitation almond extract.  But don’t buy into the hype!  This is one instance where imitation might be more cost-effective and marginally safer.

Imitation almond extract--benzaldehyde without the pesky cyanide part.

Extra nitty gritty: How an almond ends up sweet or bitter

Although a weaker (or, if you’d like to be euphemistic about it, “more delicate”) version of almond extract can be made by soaking chopped sweet almonds in vodka, the reality is that sweet almonds just don’t make enough amygdalin to yield a high proportion of benzaldehyde.  A recent article in Plant Physiology may help explain how this came to be.  The precursor of amygdalin is prunasin.  There are similar amounts of prunasin in both almonds, and similar amounts of the enzyme that converts prunasin into amygdalin.  So why isn’t there amygdalin in sweet almonds?

In this article, the authors focused on  the enzyme that breaks prunasin down: the glycosidase prunasin hydrolase (PH).  If most of the prunasin is broken down by PH, it won’t be available to make into amygdalin, with the outcome that the almond will be sweet and not bitter. The authors set out to determine whether differences in PH (not pH, mind you) might account for the differences in sweet and bitter almond fruits.  They found that in both species, there were two PHs: PH691 (identical in both species) and PH692, which contains a polymorphism resulting in an arginine residue in sweet almonds but a cysteine in bitter almonds.  This difference in PH692 might result in a different activity: perhaps the sweet almond version of PH692 is more active.

What’s more, the authors found that the localization of PH was different in the two species: while PH started out in the symplast (inside the cell membrane) and moved to the apoplast (outside the cell membrane) in sweet almonds, in bitter almonds the localization was reversed, moving from apoplast to symplast. Although the authors did not directly investigate the consequence of this differential localization, one could well imagine that if the localization of PH better coincided with prunasin accumulation in sweet almonds than bitter almonds, the result would be little remaining prunasin to turn into amygdalin in the mature sweet almond.   Further characterization of these differences may influence the breeding of sweet almonds, where avoiding amygdalin content is the primary goal.

For the scientists: Reference
Sá:nchez-Perez, R., Saez, F., Borch, J., Dicenta, F., Moller, B., & Jorgensen, K. (2012). Prunasin hydrolases during fruit development in sweet and bitter almonds PLANT PHYSIOLOGY DOI: 10.1104/pp.111.192021

For the bakers: Almond Cheesecake Recipe

Start with Better Homes and Gardens’ Cheesecake Supreme recipe

Omit lemon peel.

Omit walnuts, replace with 1/2 cup of crushed almonds (I take sliced almonds, place them between two paper towels, and crush with a rolling pin).

To the filling, add 1tsp of almond extract .

If desired, garnish with sliced almonds.

35 thoughts on “Why “Natural” isn’t always better: almond extract and cyanide

  1. Really, cool! I’m curious, does imitation vanilla have similar properties? I’ve wondered what differences there could possibly be in natural vanilla extract, imitation vanilla, and Mexican vanilla.

    • Hi Austin!
      I confess I’ve done less research here, but I think the distinction between natural and imitation vanilla extract may be more meaningful in terms of flavor, and there’s no toxin in vanilla beans to avoid. The extract of vanilla beans (from several species of Vanilla orchid, mostly the Mexican species V. planifolia) is prepared by macerating the beans in ethanol, with the result that many ethanol-soluble aromatics are present in the extract, giving a complex flavor (vs bitter almond oil, which is nearly pure benzaldehyde). The main flavor we recognize is another aldehyde, vanillin, which can be made synthetically, but pure vanillin won’t quite taste as complex as real vanilla extract. There are a few commercial preparations that make vanillin from the lignin in wood pulp; here the underlying flavor of the wood is supposed to mimic real vanilla a little better.
      An interesting note about Mexican vanilla–apparently there’s a vanilla flavoring made from tonka beans that contains the blood thinner coumarin, which can be dangerous to some people. The FDA put out a note of warning to avoid coumarin-containing “Mexican vanilla”. Make sure that you’re getting real vanilla extract made from Mexican vanilla, not any vanilla flavoring made in Mexico.

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  3. Hi, I’m interested in amygdalin as an anti cancer agent. I understand from your article that imitation almond extract does not contain amygdalin. What would you suggest as the best “safe” sources for amygdalin.
    Thanks
    David

  4. Hi, I’m interested in amygdalin as an anti cancer agent. I understand from your article that imitation almond extract does not contain amygdalin. What would you suggest as the best “safe” source for amygdalin.
    Thanks for your help
    David

    • Hi David, Please please be careful and critical in pursuing amygdalin or laetrile (the related chemical advanced by Drs. Kreb in the 1950s) as cancer treatments. There has been a very thorough, peer-reviewed pursuit of these compounds as anti-cancer agents, which has been overwhelmingly negative (for example please see a meta-study “Laetrile treatment for cancer” by Milazzo et al., published last year, covering 200 articles about amygdalin and/or laetrile in cancer, which concluded decisively that these compounds have not been demonstrated to treat cancer effectively or reproducibly).
      Amygdalin is dangerous and toxic by ingestion. Imitation almond extract does not contain amygdalin, but because of the nature of the way amygdalin is made by plants, any natural product that contains amygdalin will also contain cyanide, and even pure amygdalin, when ingested by people, will be hydrolyzed to produce cyanide by your own body. I would venture to say therefore that there is no such thing as a “safe” source. Several people have been lethally poisoned by ingesting bitter almonds or amydalin supplements (see for example “Severe cyanide toxicity from ‘vitamin supplements‘” by O’Brien et al. 2005., and “Life-threatening interaction between complementary medicines: cyanide toxicity following ingestion of amygdalin and vitamin C.” by Bromley et al., 2005, but there are many examples).
      Please talk any therapeutic decisions you are considering over very carefully with your doctor, and take care to read available PEER-REVIEWED literature on both ‘traditional’ and ‘alternative’ cancer therapies before making any decisions. I wish you all the best.

      • Hi aewills, Thanks for your prompt detailed reply.
        As a total novice in these matters I find it impossible to make any evaluation or decisions regarding cancer therapies, I’m just floundering in an ocean of information and cures, just grabbing onto whatever google throws my way, with no idea where it will take me. Do you know of any cancer therapies that have shown positive results?
        Thanks for your help

        David

      • Hi David,
        I am hugely sympathetic. There is an enormous amount of information on the internet and it can be very hard to tell what’s good science and what is bunk. This will probably seem frustrating, but as a PhD and not a physician, it would be unethical for me to try to point you towards particular cancer therapies. There’s also a wide range in what works for different people depending on the type of cancer and the patient. What I would recommend is cultivating a good relationship with your doctor, and your oncologist (and seek second opinions). Make sure that you check the credentials of any person or organization you seek advice from carefully (for example, right now I’m just some person on the internet. Why should you believe what I say? I try to make myself transparent with links to my Stanford web page and Google scholar profile embedded on my “about me” page, but if someone is giving you medical advice, demand more info).
        Here are some questions to ask anyone who’s promoting a particular therapy you’re considering (in person, online, or in a hospital):
        What are their degrees? Where and when did they get them? Are their past and present institutions nationally accredited? Is the treatment they’re proposing supported by the FDA? Did it go through formal clinical trials? Was the trial double-blinded and placebo controlled? How many patients were involved, and was the outcome statistically significant? What journal(s) are their results published in? Were those results peer-reviewed? Can you have a copy or a link to the study?
        At present, the most successful and best-validated treatments for most cancers are still surgery, radiation, and chemotherapy. But new drugs are being tested all the time in carefully controlled, well-run clinical trials.
        A well-supported, trustworthy online resource that I would recommend about clinical trials and for finding online forums and experts to chat with is the National Institutes of Health’s National Cancer Institute webpage:
        http://www.cancer.gov/
        Which has a very deep range of information on all cancer types. If there’s a particular drug or chemical you want more information about, try entering it in the search bar at Medline Plus (also an NIH service):
        http://www.nlm.nih.gov/medlineplus/
        It will give you information about what the drug is for, how it’s used, side-effects, whether it’s FDA approved, and related links to follow-up on (try out “amygdalin” for example).
        I’m sorry not to be able to offer more concrete suggestions, but there is a huge community of qualified people out there, and I hope this puts you in touch with their expertise. I wish you the best of good health and good luck in your searches.

    • Hey David, as a pharmacist (in-training), I highly advise that you talk to a licensed medical doctor on the matter. Cancer is not something you should try to deal with yourself by means of herbal/natural remedies.

      Please go seek the advice of an oncologist

      -Eric Wang, Pharm.D. Candidate

      • Hi Eric,
        This is something I’m still trying to come to terms with, you see I still believe that I have some influence over what’s happening in my body, that state of mind and spirit also play a part, but these things have no place in conventional medical wisdom – if you can’t weigh it and measure it, it doesn’t exist, and if you can’t patent it, it’s not worth investigating – that’s the prison we’ve locked ourselves into. Please don’t misunderstand me, I appreciate your concern and I’m off to have my prostate removed next week – seriously. But think about it the root of all our knowledge is human consciousness – is that just a biochemical reaction?

      • David, I agree with you. I do believe that there are many variables that western medicine misses in regards to healing. I do believe the is merit in other types of healing, but at the same time, (and i’m not saying you do this) I don’t think it would be wise to ignore the achievements of western medicine altogether

        Praying for you,

        Eric

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  7. Hi, this is very interesting information. I stumbled across this on a google search for a natural bee deterrent. Apparently Natural Tea Tree oil combined with Benzaldehyde, makes a great natural deterrent that is not harmful to bees or humans. I guess bees just don’t like the combination of these two smells and so they’ll stay right away from you…. perfect! Obviously I don’t want to hurt the bees, but we cannot risk getting stung. I didn’t know what Benzaldehyde was, so I did further research and found out it’s something found in bitter almond oil. But if I wanted to make a solution for us to use at home, is it as simple as buying some almond oil and adding some drops of tea tree oil to it before applying? Is it safe to apply directly to the skin? Do you know if there is enough Benzaldehyde in almond oil to make this effective? Or would I be better off buying this imitation almond extract? Do you know anything about this? My daughters and I are allergic to bees, and as much as we love them and know that they are a significant part of our eco-system, we don’t want to invite them around us and risk getting stung. During summer we’re often out by the pool and there always seems to be a lot of bees around… seems they are attracted to the water. I know the notion that if you just relax and let the bees do their thing, they won’t sting you, which seems to be true, however this does not apply when they get too close to the water and end up floating desperately in the pool because then they become distressed. I learned the hard way last summer when I was minding my own business just floating in the pool with the girls and a distressed bee, climbed up on my leg for safety from the water, then immediately stung me! Needless to say, there was over a month of recovery for me and lots of doctors care so if you know about this Benzaldehyde and how safe it is to use, I’d appreciate any info.

    Thank you,
    Jackie

    • Hi Jackie,
      What an interesting application! I had no idea benzaldehyde and tea tree oil could be used as a bee repellent. If the relevant ingredient is benzaldehyde, then I think you would be best served by going for imitation almond extract, which is straight benzaldehyde, and combining that with tea tree oil in whatever ratio your reading has suggested.
      I’m not certain if it extends to bees, but rosemary oil is also an effective insect repellent against things like mosquitoes and deer flies (not nearly as effective as DEET, but I appreciate your concerns about environmentalism, which are admirable in the face of the severity of your allergy!). In any case, I wish you and your daughters very good luck; a serious bee allergy must make it hard to relax and enjoy the summer weather. I’m leery of bees by the pool myself, but have only the usual aversion to the pain and swelling and itchiness of an average person’s bee sting. I’m sure you guys carry epi-pens and other emergency measures but it would definitely be great if you could just deter the bees from landing on you in the first place. All the best!

      • Thank you so much for your very prompt reply, and for the great info! Yes, we are well prepared for the potential emergency of dealing with a sting, however, as you say, it would be best to just deter the bees altogether if possible… and re-divert them to the beautiful flowers! It sure would be less traumatic for them and us as well! I will head down to the store and pick up some imitation almond extract today… (maybe even throw in some rosemary oil while I’m there… just in case!). I’m hoping this concoction works! Who knows? Maybe it’ll be the magic answer! I am always looking for good alternative solutions to this issue. : )

        Thanks again!
        Jackie D.

      • You’ll have to update me on the results of your experiments. If it seems to work well, I’ll try it myself :).

  8. Hi, I just came across this site as I was looking for info on Almond flavoring. I am hoping that David might see this post. I am an Oncology board certified nurse; my husband is a 14 year survivor of Chronic lymphocytic leukemia. You may be interested to know that there is an International Society for Integrative Oncology, comprised of researchers all over the world, investigating all matter of Complimentary and Alternative medicine. -such as tumeric, Japanese seaweed, green tea,acupuncture,homeopathic preparations; anything used to treat cancer or symptoms/side effects.
    I had the opportunity to attend one of the annual conferences, and the research is amazing. There were reseachers from Canada, Great Britain, Italy, New Zealand, India, and mainland China, just to name a few. Some compounds are way too toxic,or not active against cancer cells,but there are promising results too,like tumeric, and the study done by a researcher trying to debunk a homeopathic preparation,which should in no way work-BUT it was actually killing cells in the petri dish, and he found after a lot of research that the actual chemotoxic agent was the silica molecules from the inside of the test tube! So now he is researching that . The website is http://www.integrativeonc.org.
    Blessings, Jacqui

    • Hi Andrea, Jacqui and all,
      Thought you’d like to know I recently did an MRI scan for my prostate and they didn’t find anything, no cancer, no lesions, no nothing, the doctors explanation was that the cancer was to microscopic to be detected by the MRI. A year (and a lifetime ago) my biopsy showed 7 out of 12 cores with from 10% – 60% cancer, be interesting to see what a biopsy would show now, maybe it only develops when you remove it from the body!
      What was it that caused the cancer to disappear ? – I don’t know, but I feel the main thing is the belief that I have some influence over what’s happening in my body, there’s no way that all that power and potential sitting between my ears can’t control a few renegade cells in my prostate, but conventional medicine doesn’t include me and you in the search for a cure.
      I’ve also been doing a lot of things like Reiki, Chinese herbs, Flax oil, no sugar, no meat, sitting in the sun, jogging and more and I’m sure they all helped, but the main reason I’m writting to you is I came across this 10 day cancer cure (http://www.healingcancernaturally.com/aloe-vera-honey-rum-treatment.html),
      The recipe was:

      300 grams fresh Aloe arborescens leaves
      500 grams pure bees honey
      4 Tbls. alcohol

      Blend in blender, take 1 tablespoon 3 times a day for 10 days

      Well I have this Aloe plant that’s been waiting outside my front door for years, it was 10 days before the scan, how could I not do it? What do you think, can it really be a cure?
      Really like to hear your thoughts.

      (:David

      • Hi David!
        That is beyond wonderful that your prostate cancer appears to have fully remitted. I am so very happy to hear it! If you don’t mind my asking for clarification, did you undergo chemo, surgery, or radiation for your initial cancer, or were your own natural remedies all you pursued?
        I am certainly persuaded that positive thinking has an impact on our bodies. I think all medical researchers would agree that the placebo effect can be real–or we wouldn’t go to so much trouble to control for it! And so I hugely encourage a positive and empowered outlook.
        Do I think your aloe consumption cured your cancer or stopped it from returning? No. I can’t prove it didn’t, of course, and wouldn’t want to, but I think it’s equally likely that the toast you ate for breakfast in September or the TV you watched in October cured it–it’s hard to prove those didn’t, either. My perspective is that things that are effective treatments for disease are statistically reproducible, and biologically describable. Aloe has been studied a lot, and has potential health benefits, but if it reliably made a difference in cancer progression, believe me, dozens of NIH-supported researchers would be making their living off of it by now (as is the case for other botanically derived anti-cancer agents, like Taxol, colchicine, and cyclopamine). Might it have helped you? Possibly! But as we say in science, n=1, and it’s hard to evaluate without controls, blinding, and statistical power.
        That being said, aloe is not harmful, and potentially good for you, so I’m all for you taking it. My only caution would be that you (1) please continue to get your follow-up scans and keep an open relationship with your doctors, and (2–and you don’t seem like the kind of person who would do this but just in case…), please don’t use your (wonderful!) success in improving your own health to lead you to suggest that your friends or loved ones discount their doctors’ advice if they have the misfortune to fall similarly sick. Every cancer patient deserves friendship and support and a positive attitude, and the full gamut of medical care and consideration that goes into their unique case.
        Congratulations, and I wish you all the best in ongoing good health and happiness!

      • Hi Andrea, Thanks for your reply, the reason I sent the same comment twice was because I didn’t see a copy of what I sent on your home page, so I thought you hadn’t received it.
        I’m happy to be able to have this conversation with you.
        I healed myself, although I came under a lot of pressure from friends, family and doctors, I declined the knives, ray-guns and robots that were offered to me.
        In response to your assertion that treatments should be “statistically reproducible, and biologically describable” I would say that statistically significant research requires a huge investment and investment implies that there will be a greater return on money invested, natural cures will not give that financial return. Profit and not our well being is the priority.
        Biologically describable? does that mean that if there’s a cure that works, but we don’t understand how it works, it’s not valid and should not be used. What’s missing from the formula in conventional medicines search for a cure is you and me. Its all to do with biologically describable functions and chemical reactions, we’re so much more than a series of chemical reactions, but we don’t have the tools or the understanding to evaluate what part WE play, we can’t see beyond our prison of logic and reason, cause and effect.
        The human spirit, positive thinking, consciousness, empowerment, these are elements that current research methods of statistical trials and placebos have no way of evaluating, they play no part in the cure, but I’m sure you won’t deny their influence.
        I’m not the same person I was a year ago, I understand today that you have to treat the cause and not the symptoms if you want to find a cure.
        I’ll be doing PSA tests every couple of months and I’m seeing the doctor again in 4 months.
        I’m not sure about your suggestion to let others take their doctors advice, I didn’t, even though they put the fear of God into me and almost bullied me into getting rid of my prostate with all the irreversible consequences that can cause, was I wrong to believe in myself?
        I think there is a trend today towards active surveillance and I would like to think that if I can do it so can others. Especially with prostate cancer which is usually slow developing and you have time to evaluate its progress – or not.
        Thanks for being part of my journey.

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  10. wow…I can’t believe in this day and age people are still propagating the falsity that the Hydrogen Cynide, one of the most effective ingredient in fighting cancer, is in any way toxic to us. The FDA and the national Cancer Society way back in the 1960′s (in an attempt to discredit Atreal) proved very much effectively that Hydrogen Cynide found in the seeds of Prunus are in no way toxic. Shame on you for even writing this article. Numerous medical publications proving this, very easy to find.

    • Jim,
      I would be really happy to have a continued dialog about this. What are the FDA and NCS studies you were thinking of–could you give citations please? Because hydrogen cyanide, delivered orally, by inhalation, or through the skin, is pretty universally acknowledged to be toxic. Here’s a list of quotes and citations from some of our major national and international health organizations:
      1. Centers for Disease Control: “Hydrogen cyanide (AC) is a systemic chemical asphyxiant. It interferes with the normal use of oxygen by nearly every organ of the body. Exposure to hydrogen cyanide (AC) can be rapidly fatal. It has whole-body (systemic) effects, particularly affecting those organ systems most sensitive to low oxygen levels: the central nervous system (brain), the cardiovascular system (heart and blood vessels), and the pulmonary system (lungs).” http://www.cdc.gov/niosh/ershdb/EmergencyResponseCard_29750038.html
      2. Occupational Safety and Health Administration: “exposure to cyanide can result in symptoms including weakness, headache, confusion, vertigo, fatigue, anxiety, dyspnea, and occasionally nausea and vomiting. Respiratory rate and depth are usually increased initially and at later stages become slow and gasping. Coma and convulsions occur in some cases. If cyanosis is present, it usually indicates that respiration has either ceased or has been inadequate for a few minutes. If large amounts of cyanide have been absorbed, collapse is usually instantaneous; unconsciousness; often with convulsions, is followed almost immediately by death.”
      3.National institutes of Health (via pubchem) “Hydrogen cyanide is readily absorbed following inhalation, oral, and dermal exposure.”… “The release of excessive amounts of HCN gas into the breathing zone of workers can result in collapse and death within seconds to minutes.”…”
      4. World Health Organization: http://www.who.int/ipcs/publications/cicad/en/cicad61.pdf “The principle features of the toxicity profile for cyanide are its high acute toxicity by all routes of administration…”

      Perhaps more telling, there are many case reports on Pubmed (the National Health Institute’s archive of medical literature) of people dying or falling extremely ill from cyanosis specifically from consuming bitter almonds or apricot kernels: here are several profiles. One, another, a third, fourth, and a fifth, for example.

  11. Hi,
    I’m m reading ‘love in a time of cholera’ and found your site when trying to work out the connection of bitter almonds and cyanide.
    Now I know so thanks! Really interesting article.

  12. I would like to know how they make the artificial almond flavouring because I have often had problems with headaches from flavourings (especially from the generically labelled ‘natural flavors’ and from Vanillin). I’m trying to find out what it is about various flavourings that give me these headaches. Natural flavors are made out of so many bizarre things (like beaver’s anal gland secretions) that it’s really surprising more people don’t react negatively to them. I know other people who do respond the same way as I do (with headaches and nausea), but I’ve never had artificial almond extract to see if I react that way to it (I’ve avoided it due to my other reactions). It seems also a bit silly to avoid the natural extract just because it might have trace amounts of cyanide in it. Usually when you use almond flavouring you use it in a matter of drops, so the amount listed as being fatal would never be consumed in one sitting.

    • Hey Dawn!
      There are many ways to make benzaldehyde synthetically–it’s not a very complicated molecule; the basic structure of this hexagonal group with something dangling off the end of it (a phenyl group) comes in lots of very reactive types that are pretty easy to convert over to an aldehyde. But many of the starting products one might use (phenol and toluene come to mind) are pretty toxic and unlikely to be used in large-scale commercial food synthesis. Benzoic acid is not very toxic, so commercial producers may use that, or might use reflux of cinnamaldehyde, since that’s another flavoring. It’s also possible that different manufacturers may use different syntheses.

      Are your headaches with nausea migraines? Some migraineurs have specific food flavors or smells as a trigger (the umbelluone in bay is a common one). If they’re a frequent or severe problem, you might want to talk to your doc about triptans, which can help prevent them. As a migraineur myself, I definitely sympathize with wanting to avoid triggers, and I will say that I find phenol (the distinctive smell in chloraseptic spray) to be potentially headache-causing.

      I think if you know you do ok with natural almond flavoring, stick with that. My argument is not so much that natural almond flavoring is dangerous (in normal amounts) as that it’s unnecessary, especially if it’s more expensive. But in your case it might make sense. And then if you do eat anything else almond flavored, keep tabs on whether it’s natural or artifical and how you feel after.

      Good luck!

  13. This is all very impressive reading. Long long ago, I happened to be a terrible, but dedicated chemistry student, but somewhere way back when, I remember “Don’t eat almonds with……..” because of the cyanide- poison “thingy”. Was it oranges? does this sound familiar to you? I’ve been eating raw and home roasted almonds daily, all winter long and can’t get enough of the navel orange season… so this has been swirling from the back of my mind now to the front…. So am I in trouble with my big mug of tea, handful of almonds and a navel a couple times a day?
    Thanks.

    • Hey Suze!
      I think you’re probably ok with any combo of almonds and oranges. There’s essentially no way to generate cyanide from regular, mature, “sweet” almonds. May have been an urban myth? There are a few other rosaceae species that have small amounts of cyanide sequestered in various places–apple seeds, pyracantha berries, possibly crabapples, but the whole deal with cyanogenic plant material is that you’ve have to purposefully ingest a whole lot of something unpleasantly bitter tasting (or a concentrated extract thereof) to do yourself harm.
      Almonds, tea and navel oranges are favorite snack combinations for me too :).

  14. I bought a sweet almond tree that promptly died to the ground, but alas the next spring sprouted new growth. I now assume it is bitter almond root-stock since that is fairly routine i read. It is a vigorous plant with pink flowers. Last year it made a ton of almonds that all mysteriously disappeared before any were ripe which I read is what bitter almonds do. Now I have done some research and feel fairly confident it is a bitter almond tree. Do I have to kill it if it doesn’t ever make Mature almonds? Is this plant dangerous?

    • Hi Kay,
      It’s a shame you lost your sweet almond tree! A bitter almond tree wouldn’t be at all dangerous, just not edible. People use all kinds of far more toxic plants as ornamentals (look at how many people use oleanders for hedges!), and bitter almond trees are still nice to look at.

  15. Cyanide can be good for you. Ignorance in not bliss. Water, too, can be a poison when it dilutes the body’s electrolytes. Cyanide is good for you. We consume it in a variety of foods. Please, at least obtain a PhD in organic chemistry and another in human biology before issuing warnings based on info tid-bits. Asians use bitter almonds in cooking, and have done so for milleneae, and are alive to give you their tasty recipes.

    • Hi Alicia,
      Well, my Ph.D. is in molecular biology, not organic chemistry, and I work in the Genetics department at Stanford Med school, so I feel pretty confident in my credentials on human biology…and I still feel comfortable standing by the viewpoint that if it’s not necessary to ingest cyanide, it’s not preferable to do so. Cyanide is an incredibly effective inhibitor of cytochrome oxidase (I think cyt c oxidase), which is necessary for oxidative phosphorylation. In essence, it prevents cells from using oxygen to make energy in the form of ATP. While it’s true that in very small quantities, cyanide is not toxic to an adult human, it’s still not necessary, or to my knowledge, beneficial. I’m willing to be educated about the cellular basis of any potential benefits.
      My stance is not that small amounts of bitter almond extract will kill you, or even that it’s terribly dangerous. It’s just that ingesting cyanide, when you’re after benzaldehyde, is a bit silly.

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