Thread: Nature identical compounds
Hello all. I've been limiting myself to essential oils but now I'd like to include some nature identical synthetic fragrance oils in my blends. Where do I look for them? New Directions Aromatics has a selection but it is quite small. Are there other outlets?
Is there a resource that lists fragrance oils that are usually nature identical and others that do not occur in nature?
Also, which accords can never be nature identical? For example, is it impossible for a certain fruit accord like mango to be nature identical?
My definition of Nature Identical is a chemical which is found occurring in a natural product (an Essential Oil or Absolute) but which has been made synthetically in a laboratory etc. Sometimes it is not possible to extract the chemical from the natural so it is easier to make it synthetically. Often the synthetic version is much cheaper. Most fruit bases will be synthetic as it is often impossible to extract those chemicals which go to make it from the stating fruit. It may be that many of the chemicals in the base will be nature identical, others will be non nature identical.
It is unlikely. The fragrance house isn't going to divulge it unless they pride themselves on using one or the other (for whatever reason). IN that case their marketing information may disclose it. However it is unlikely. The ingredient declarations will declare the same base chemical (eugenol for instance) whether it comes from a natural or as a lab derived, nature identical synthietic.
Some of the synthetic musks were synthesised prior to being found in natural materials (omega pentadecalactone for example was being sold as Exaltolide prior to being found in angelica root). So now you could say that exaltolide is a nature-identical material, but before that discovery was made it would have been classed as non-nature identical. Itís the same stuff . . .
Omikron has a handful of oils it sells that it calls nature-identical. The site's in German, though: http://www.omikron-online.de/cgi-bin...&gesamt_zeilen=
Thank you all once again. I guess what I'm looking for is a database of perfumery compounds stating which compounds are nature-identical (whether natural or synthetic) and which ones do not occur in nature. It doesn't matter whether the compound is synthetic or not, just whether it occurs in nature or not.
For example, before I decide on ordering a certain aldehyde, how can I find out if it occurs in nature or not?
Google around for it, use aroma comapny literature (spec sheets) to determine the origin of their material, call the distributor of the chemical in question. You're not going to find a comprehensive public database giving what you want.
Have you looked at the Good Scents Company page? (to see if -and where- chemicals have been found to occur in nature)
omega-pentadecalactone - if you look under ĎOccurrenceí youíll see some of the natural sources. If, at the time Bill put his page together, it had, to his knowledge, not been found in nature it will say Ďnot found in natureí. As Iíve said that can never be definitive: it means exactly what it says Ďnot foundí isnít the same as Ďdoes not occurí and knowledgeable though he is even Bill doesnít know everything . . .
JC may I ask you why you are so interested in using nature identical chemicals but do not want to use non-nature identical chemicals? This, to me, makes little sense.
in some circles, Ruzicka is credited for the discovery in 1928 in angelica root, while
others state it was found in 1927 by Max Kerschbaum.
Then in 1930 firmenich filed the trademark for Exaltodilde, but there is some record of sales as early as 1927-28 ?
One might equally use the example of alpha-ionone, where the researchers were attempting to recreate the molecule responsible for the scent of orris and were convinced they had done so, when in fact the material they had produced was not the alpha-irone of orris root, but alpha-ionone of violets. A matter later sorted out by the said Ruzicka, who is probably more famous for his work on Civettone and Muscone (if famous is the right word for this kind of highly specialised stuff!). It was some years later that the ionones were understood to be responsible for the scent of violets and alpha-irone was successfully synthesised.
that maybe the case if one assumes firmenich had synthesized this prior to the discovery, as you mentioned
the trademark is post-date discovery in many trademarks, however, Ruzicka was the first to synthesis this after the initial discovery - 1927-28 as that was the old practice then, they would try to synthesis a discovered molecule to confirm the initial discovery.
so in this case it was identified in nature prior to the synthesis.
Last edited by Chris Bartlett; 6th May 2014 at 06:31 PM. Reason: minor corrections
"Exaltolide was first synthesized in 1928 via the oxidation of Exaltone"
and in the book Concise Encyclopedia Chemistry credits Ruzicka as the first to synthesize this in 1928
which seems to confirm Firmenich's statement.
there is a preview of that book on google
and in other pdf book i have "Chemistry and Technology of Flavours and Fragrances"
Max Kerschbaum first discovered exaltolide in angelica root oil in 1927
it appears at least in this case exaltolide was first synthesized approx. 1 year after it was discovered / identified in nature.
I'm not interested in engaging in a game of contradiction for its own sake. Do you have something helpful to contribute to the OPs question?
excuse me?, you asked me for references in your previous post, so my reply was relevant to your query.
I am also curious as to why you would like to work with (or know if something is) nature-identical.
Last edited by PerfumerSupplyHouse; 7th May 2014 at 04:05 AM. Reason: error in spelling
Well, I would like to use nature-identicals where the actual naturals are too difficult to extract. Philip Kraft at Givaudan makes a point of this. In my case being a naturalist, I would prefer to use for example synthetic Methyl Jasmonate instead of its hydrogenated form methyl dihydrojasmonate ie Hedione, as it very much exists in nature and doesn't have any of those nasty trans-isomers.
I realise that it's difficult being a Naturalist and sometimes one has to go to the Dark Side but only where ones chemicals of choice aren't otherwise available. I also believe that hydrogenation and biosynthesis of naturals is a grey area and one sometimes has to go there as well.
I can sort of understand why anyone would want to make an all Natural fragrance, although I don't agree with the philosophy behind it. I cannot understand why you only want to use those chemicals which have been found occurring in nature but don't care how they are synthesised. The synthetic version is the same as the natural (with some exceptions, differing optical isomers) so why, if that is OK, won't you use chemicals that do not occur in nature but have been made using the same synthetic processes? What is the inherent magic of a chemical occurring in an Essential oil,( but made synthetically) that a chemical not occurring in an Essential Oil, does not have?
you wrote, " I would prefer to use for example synthetic Methyl Jasmonate instead of its hydrogenated form methyl dihydrojasmonate ie Hedione, as it very much exists in nature and doesn't have any of those nasty trans-isomers. "
methyl dihydrojasmonate is actually found in nature, so if you are ok with the synthetic methyl jasmonate
what would be the issue with synthetic methyl dihydrojasmonate?
also why are trans-isomers nasty?
http://www.essentialoils.org. And perfumers seem to be taken by the high-cis versions rather like we avoid eating bad hygrogenated trans-fats. I say go with the real thing like lard or butter instead of margarines.
Won't natural isolated chemicals and synthesized ones differ in their impurities (as well as isomers balance), and hence smell slightly different?
according to a PHD chemist at Firmenich in 1958, methyl dihydrojasmonate was discovered in jasmine.
it is also found in some teas and heliotrope
a hydrogenated trans-fat is a completely different animal
than a trans aromatic isomer.
Last edited by luigi_g; 7th May 2014 at 05:17 PM.
Wow. Great advice, everyone! Definitely have several options of finding out whether or not a chemical occurs in nature.
Please forgive me - this is as far as I will go in defining my argument. I prefer to stay away from lengthy debates.
Also, I'd like to be able to incorporate fruity notes in my blends, which are hard/impossible to extract from fruit (except citrus). So the next best thing in my mind would be a compound that is identical to the natural scent molecule(s) of watermelon. A compound with a similar scent that does not occur in nature is like a new drug that has just been approved by the FDA but may prove to be unsafe after a few years of consumption by the general public.
That's my thought process I hope it makes sense.
this is my first post here on basenotes, I'm not knowledgeable on perfumery (yet), however I have a Phd in chemistry so I really couldn't resist putting up some extra info in this thread. (Please not that I have nothing against the use of "all natural" compounds)
When it comes to chemicals of which we know they occur in nature, there are two main difference between the chemically made compound and the one extracted/purified from the natural source.
The first is the ratio of carbon isotopes, but this determination is far beyond the capability of our noses (I'm sorry if I've offended anyone with this statement) and it is irrelevant to perfumery. It can however be used analytically to determine if your "all natural" marketing claims are true or not.
The second difference is more important, and was mentioned above. Both samples will contain different impurities. While purification techniques are very powerful nowadays, resulting in 99+% purity for both samples, if one of the let's say 10 impurities at 0.1% has a scent, trained noses will be able to sniff out the difference. Whether or no not the natural one smells better will be up to coincidence, as much as you may disagree.
The cis-trans discussion is a mere question of purity. Chemists generally regard a cis isomer to be a completely different compound from the trans isomer. In fact, we try to disregard the similarity of their names as much as we can. Think of it as you and your brother/sister. You share a name, but I'll treat you differently. Do note that a trans or cis impurity can be present in both naturally derived or chemically derived compounds.
Optical isomers (which are eachothers structural mirror images) have long been regarded as the same coumpounds, but this is nowadays also completely out of the question. Think of them as twins, difficult to tell apart at first sight, but once you know them, they are completely different people. In fact, a perfumery relevant example is carvone. R-(–)-carvone smells like spearmint. Its mirror image, S-(+)-carvone, smells like caraway. Again, this is all up to the power of the purification method. S-carvone would be considered an impurity. An annoying one as it carries a scent. The reason why synthetic compounds having optical isomers are still often sold as mixtures is because it is more difficult to make them as one isomer and/or to purify them. In practice, this is only done for pharmaceuticals. Optically pure aromachemicals will most likely be purified from natural sources.
So far for the technical part, now some philosophical remarks:
If i use plain old sugar, convert it chemically to hexenal and purify it extensively, comparing it to an equally pure natural sample, there is no difference in carbon isotopes, there is no analytical technique in the world which could tell the difference, the toxicology is exactly the same and a perfumer saying he can smell the difference is just lying. Why in earth would I then use the naturally derived compound? In fact, you would be surprised how efficient chemical processes are, and quite often chemical synthesis is less demanding on the environment as compared to extracting crops and purifying the very complex mixtures you get from it.
Safety is one argument that may be used, but the chemical industry is one of the, if not the most strongly regulated one. These chemicals are for external use only, and those which are allowed have passed extensive tests. And let's be honest, you don't need to be worried about the 'long-term effects' of something which you come into contact with twice a week in extremely low doses. Just stick to well known, pure compounds from trustworthy sources.
A more reasonable argument is the scent. For real world samples, some impurities change the scent slightly. Go with the one which smells best or works best for what you are trying to achieve. Even if its the synthetic one.
And probably the argument used most of all, and which I can't argument against: marketing.
When it comes to chemicals which are not known in nature (yet), just know this: There is no reason why plants wouldn't make toxic chemicals, just as much as there is no reason why humans wouldn't make non-toxic chemicals.
I fear I've been ranting....
A corrolary: It would be more a matter of chance if a random new lab chemical ended up participating in natural biological processes as harmoniously as a chemical with a practically infinite existing history of benign/helpful participation in such natural processes.
I see nothing less than rational and scientific about that theoretical standpoint. Seems intuitive and "commonsensical" to me. I would think it straightforward to find countless ways to support those hypotheses with data.
Last edited by DrSmellThis; 8th May 2014 at 02:46 AM.
I feel that the water is being muddied by the various comments that have been made. The safety argument is spurious. Linalool from Ho Oil is as safe (or as toxic) as Linalool made synthetically from Turpentine. No chemical that is shown to be toxic will be used in Perfumery, indeed many have been banned over the years, both natural and synthetic. Some of the most potent poisons are naturally derived. A natural extracted chemical will usually be less pure than the same chemical made synthetically. If it is considered necessary, purification can be increased. As has been mentioned above cis and trans isomers are different beasts, and should not be substituted one for the other. Synthetic and natural versions of the same chemical may show different optical isomerism; typically the natural extract will either be one or the other, the synthetic will be a racemic mixture. It is now possible to separate these if necessary.
I cannot see any possible reason to distinguish between chemicals which are nature identical and those which are not; especially when non nature identical chemicals can be used if there is nothing else that is suitable.
As to the original question, then, I personally do not consider the difference between nature identical lab chemicals and chemicals derived from natural (vegetable) sources to be meaningful. Differents in trace impurities should be trivial, if you have a high quality product.
Isn't a natural-source version of linalool used pretty commonlty, from basil? I had a sample, but forget how much it was.
I largely agree with the things posted above. In fact, the term “nature identical” seems to me to be only a marketing term. It is used to sell synthetic compounds to people who otherwise would not, because they were misinformed on the supposed dangers of chemicals.
I think making a distinction between ingredients, the stuff you buy, and chemicals, a theoretical 100% pure sample would be useful to understand this whole discussion.
Any ingredient you buy, including the essential oils, is a mixture of chemicals. The source of these chemicals (nature or synthesis) is irrelevant. The constitution of the mixture is what really matters. A 99,99% pure sample of chemically made ethanol is perfectly safe. A completely “natural” oil containing many hundreds of safe chemicals, but 0,01% cyanide is unsafe.
Dosage is in this respect an important aspect. Actually, there is no such thing as a toxic chemical, there is only “toxic at doses above x mg/kg bodyweight”. There is probably no doubt in anyones mind that the main constituent of perfume (ethanol) is lethal if you drink too much of it. Still, nobody seems to be worried about this. An ingredient is safe only if all the chemicals included in it are below their toxic doses.
Iím not sure that either argument carries more weight than the other. It is simply more sensible to judge the relative safety of each material on its own merits.
On the question of cyanide btw you might like to take a look at my post about Bitter Almond Oil for an interesting take on an ingredient that isnít generally what it appears.
Chris, I quite liked your post about bitter almond oÔl, but that hydrogen cyanide smells like benzaldehyde is an urban legend. I've had the "pleasure" of smelling it several times, during my work. It has none of the depth and sweetness of benzaldehyde, and is a very "dry" kind of scent. (If that makes sense)
now back to the topic I guess
Hi Thomash. Love your chemistry posts.
I have often wondered about nature identical compounds and this thread is making it very clear that they are extremely unnaturally natural. It takes a fair bit of re-reading.
Glad you enjoyed the little romp around the Bitter Almond topic - I’ve never smelt cyanide and was quoting Arctander - most of his smell descriptions are pretty spot-on but I have no plans to test which of you has it right on this particular question: smelling cyanide isn’t on my bucket list!
Last edited by Chris Bartlett; 9th May 2014 at 08:38 AM. Reason: minor corrections
Imagine linalool contaminated with 0.01% of 2-isobutyl-3-methoxypyrazine: it would smell like freshly cut sweet pepper, not like woody-roses. Most of the time this sort of thing doesn’t matter because in practice the contaminants that remain in a product are near-odourless, but it’s rare that a perfumery material is as pure as 99.99%: most perfumery products are in the 92-98% range and some as little as 50% of the named product. But of course much work has gone into purification to the degree necessary to get the right compromise between cost and odour, while remaining safe in use: whether the source was natural, nature identical or completely novel.
Purity and safety are, as you rightly point out, not at all the same thing.
BTW you refer to the term ’nature identical’ as essentially a marketing term, which is also my understanding. I believe it originated with flavours, which at one time were routinely categorised into natural, nature identical and artificial. The middle category was dropped some years ago in response to growing consumer distrust of it. Now flavorists talk about degrees of naturalness in a different way: natural flavours may be described as FTNF or FTNM (from the named fruit / material) in order to distinguish them from natural flavours derived in some other way, such as for example using vanillin produced from lignin from wood-pulp rather than extracted from vanilla beans or phenyl ethyl alcohol produced by fermentation rather than by extraction from roses.
Last edited by Chris Bartlett; 9th May 2014 at 08:41 AM. Reason: minor corrections
This is off-topic, but with regard to the pharmaceuticals, have a look at this paper in a very reputable scientific journal:
j.nat.prod. 2007 p461
Only the N category contains nature identical ones (5%), some people may include the B and V, but it still only adds up to less than 25%.
The confusion about the smell of cyanide is probably caused by it being so historically entwined with the almond oil. Probably early descriptions of the scent had some benzaldehyde in it as contaminant. Its difficult to convince people to actually smell cyanide, understandibly, and many chemists even remain convinced that cyanide smells like benzaldehyde even if they have never actually smelt it. Its funny to see how anxious people get in a lab when you spill harmless benzaldehyde. When we were working on the cyanide project, no benzaldehyde was ever involved and none of us three ever smelt it or anything like it. You can see the setup here, but its fairly technical
tetrahedron letters 2010 p4189
One guy could never smell anything apart from the acetone and acetic acid we were using (there is a genetic predisposition if you can smell cyanide), but me and my colleague could always independently detect if there were small leaks. We both agreed that it was a very dry kind of scent. The intensity of this scent was closely correlated to how light-headed we got after the experiment, so I am pretty sure that this was the cyanide. Mind you, I wouldnt voluntarily work on such a project again...
Im sorry for not linking directly to the references, but I cant post URLs as a new member...
I can smell them apart in a second because the one is clearly offensive and the other smells clean.
The human nose can detect some impurities at levels that equipment can miss.
As far as the smell of cyanide is concerned Iíve really no idea how Arctander came to the description he did, but I do know he spent a lifetime learning smells and describing them and produced, what is still today, regarded as the definitive work on the subject. If you havenít had a chance to read his work I can really recommend it: I have the well-known work on naturals and the less-well-known work on synthetics and both are superb and highly educational - the latter is sadly out of print but the former is available online and from Allured Books. (if you use the Jump To facility in the Haithi Trust edition to go to 52 you can see what he had to say about hydrocyanic acid).
That doesnít mean to say he was right in this case and anyway olfaction isnít quite like that - there isnít a right or a wrong - itís perfectly possible to take three people and find that one smells nothing at all, one smells a musky scent and the third a light, bright floral - they are all smelling benzyl salicylate: there is no reason cyanide might not work in the same way. I still have no desire to find out for myself however ;-)
I think there is only one conclusion, the term nature identical was invented to confuse people and still does it very efficiently We should do away with it completely, and accept that there are 2 clear classes: natural and synthetic, both with their own merits. (and some intermediate classes like fermentation produced, semisynthetic etc. but lets discuss that only when needed)
I have smelled an old sample of Potassium Cyanide, and I could smell a strong almond note; similar to Benzaldehyde. As I didn't have some Benzaldehyde at hand I couldn't do a direct comparison, but still.
I don't care about discriminating between ingredients and chemicals, and that is not the point of this Topic. It has been suggested that whilst chemicals that occur in natural products but have been made synthetically are OK to use in Perfumery; those chemicals which don't occur naturally and have been made synthetically are not OK to use. To me, this is illogical, and daft.
I don't care about the source of pharmaceuticals, nor the efficacy of pheromones. Neither have anything to do with the topic.
When people are sick they don't care where the pill comes from, it's been shown effective and safe. The same should ideally be true when people want to smell nice.
The cyanide, maybe some people do indeed perceive it with an almond note, I can of course only speak of my own perception of it.
you mentioned fermentation produced, wondering what your take is on that.
to me fermentation produced, and some of the other approved natural processes are just as confusing or more so, than
for example beta-ionone, if made via an organic reaction, it is classified as synthetic beta-ionone
yet, if made via a fermentation process it is sold as natural beta-ionone, rather misleading.
natural beta-ionone is optically active, the fermentation process beta-ionone is racemic.
more troubling is the new synthetic biology, GMO organisms have caused some panic, but synthetic biology is extreme,
this is entirely new DNA sequences, specially designed to preform unnatural tasks, yeast producing vanillin, as an example.
sure the fermentation process is natural, so the argument is, the product will be natural, BUT there is nothing natural about
Luigi, you've asked a very difficult question and I will definitely get back to you on this. (my answer is too lengthy to write down, this late on a Friday evening)
basically, the idea is the same. The product which results from these processes is chemically the same as the one coming from other processes. After fermentation, they are purified to such an extent that they are suitable for perfumery, which means free of odorant side products. You can see that they are more similar to synthtics than to naturals, which are traditionally a mixture of several different chemical species.
As a perfumist, that is about as far as you should read. Fermentation produced chemicals are with regards to their use very/completely similar to the chemically produced ones.
How to classify them? This would depend on the actual process. In some cases you can still regard them as natural. If, for example someone would manage to grow actual actinobacteria in a production environment, you could argue that the resulting geosmine is of natural sources. In practice however, bacteria and yeasts that produce scented chemicals are not very fond of production environments. I havnīt heard of one actually, but you can correct me if Iīm wrong. And indeed, then GMOīs come into play. Usually, these GMOīs have been optimised to such an extent that they would in fact be unable to survive outside the production environment. The energy they unknowingly invest in the production of large amounts of aromachemicals makes them weak in the competitive outside environment. They are more "constructs", assemblies of the correct DNA fragments and enzymes, then they are organisms. In that sense, I would not regard this type of production process natural, even though it is biological.
Again, its all just a name for a product. The fact that the process has a more natural feel to it, has been used by the gen-tech people to create a niche for themselves, setting their product apart from the chemically synthesized one. And asking slightly more money for the product perhaps. Is the product itself any better? No. Is the process more environmentally friendly? In some cases.
On a side note, please donīt be worried about your personal health when it comes to GMOīs. These organisms are "constructed" from the same basic building blocks of all living beings. Your body/digestive system is perfectly equiped to handle any combination of genes and proteins. Even if you had never heard of e.g. cucumbers before, never had contact with them, never eaten them before, you could still safely consume this specific combination of genes/proteins/sugars/etc.
Synthetic biology is just a very advanced form of gentech, which instead of modifying existing organisms, builds them from scratch. As far as Iīm aware, it is still far from being applicable in production.
As to the environmental question, that’s much harder to assess because often synthetic fragrance materials are made from waste products - such as turpentine (a waste product of the paper industry) or chemicals that are ‘left over’ from production of something else. Then again often they are not - they can be produced from fossil fuels or by deconstruction of a natural starting material that is otherwise in demand.
I’m aware that an analysis has been done on the total fossil fuel consumption, carbon footprint and other environmental impacts comparing synthetic menthol (produced from citral) and natural menthol (produced from mentha arvensis oil), which reached the counter-intuitive conclusion that the synthetic had markedly less negative environmental impact (specifically used less fossil fuel and produced less carbon emissions). I’m not aware of any equivalent work for other materials though so the results could be quite different.
Last edited by Chris Bartlett; 12th May 2014 at 06:54 PM. Reason: more minor corrections
This technology and production is ongoingSynthetic biology is just a very advanced form of gentech, which instead of modifying existing organisms, builds them from scratch. As far as Iīm aware, it is still far from being applicable in production
a link to the criticism;
Last edited by luigi_g; 12th May 2014 at 08:43 PM. Reason: correct link