Vetiver, Vetiverol, Vetiveryl

Serg Ixygon

Well-known member
May 2, 2015
Can somebody explain the difference in producing that materials and smell?

Vetiver oil is made of vetiver roots directly.
Vetiveryl Acetate- it is a product of acetalization of whole Vetiver oil? Or some fraction was separated from the oil before acetalization? And what this process gives for perfumery goal? VA- it is not a single molecule it's still a mixture of everything?
Vetiverol- it is a single molecule made of not Vetiver oil at all? If it's so why there is a note- ex Haiti, ex something? Is it smell very different from Vetiver oil?
Thanks.
 

David Ruskin

Well-known member
May 28, 2009
Vetiver oil is an Essential oil made by steam distilling Vetiver roots. The major component of this oil is Vetiverol (about 50.0%), and it may be isolated from the oil. It is made up of several isomers, and as always when isolating from an Essential oil, the source of the Vetiverol can have an effect on its odour. There will always be a difference between an Essential oil and the major component from that oil (think of Clove Bud oil and Eugenol), the oil being more complex. The oil will smell of Vetiverol plus other chemicals, and the amounts of those chemicals will vary as the source changes. Vetiverol can be acetylated to give Vetiveryl Acetate. Like all acetates compared to the parent alcohol, Vetiveryl Acetate is sharper, sweeter, and (some say) stronger. There was quite a lot of Vetiveryl Acetate in the original formula of Guerlain's Vetiver.
 

Geco

Well-known member
Jun 14, 2015
To my nose: Vetiver absolute oil are more earthy/radish tone, more deep and dark, Vetiveril Acetate is more sweet and "peanuts" tone ,a scent present in many modern perfumes...
 

Serg Ixygon

Well-known member
May 2, 2015
THank you, Geco. Does the quality of VA depends from producer the same as oil?
 
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Jim Conti

Member
Jun 22, 2016
I wasn't expecting much difference between some vetiveryl acetate ("generic")that I had on hand and some that I recently purchased (Ventos), but there was, and I was pleasantly surprised. I guess it's like a lot of other things that go by the same name but in reality can be quite different

Also would like to say that I really enjoy reading your posts.
 

David Ruskin

Well-known member
May 28, 2009
You can get at least two types of ingredient both called "Vetiveryl Acetate". One is the result of the acetylation of extracted Vetiverol, the other the product of the acetylation of Vetiver oil. They will smell different.
 

Jim Conti

Member
Jun 22, 2016
I also recently purchased vetiverol as well, but haven't gotten around to sampling that yet. For some reason I seem to have a preference for scents that start out or reference woods and grasses, whether they are natural or synthetic. I like Leaf Alcohol and how it smells like freshly mown lawn. It also has a smell that suggests it would feel "oily", which is an odd thing to me, that scent would have a haptic component that you would feel...

I'm having a hard time understanding the materials that are, I think, referred to as "fractionated". Are they a further "distillation" of a natural or a (re)construction of particular synthetic molecules present in the natural material. Or could they be either?

When starting out I received from IFF samples of a Peppermint Oil, a Peppermint Absolut and a Peppermint "Heart", which I believe is a fractionation. The Oil was obvious, the Absolute helped me to understand "freshness" and what can happen when heat doesn't enter the process, but the "Heart" still has me confused. I understand that it is only part of the Peppermint, but how it can small like burning electronics, which has its own strange kind of appeal, amazes me.
 

David Ruskin

Well-known member
May 28, 2009
I also recently purchased vetiverol as well, but haven't gotten around to sampling that yet. For some reason I seem to have a preference for scents that start out or reference woods and grasses, whether they are natural or synthetic. I like Leaf Alcohol and how it smells like freshly mown lawn. It also has a smell that suggests it would feel "oily", which is an odd thing to me, that scent would have a haptic component that you would feel...

I'm having a hard time understanding the materials that are, I think, referred to as "fractionated". Are they a further "distillation" of a natural or a (re)construction of particular synthetic molecules present in the natural material. Or could they be either?

When starting out I received from IFF samples of a Peppermint Oil, a Peppermint Absolut and a Peppermint "Heart", which I believe is a fractionation. The Oil was obvious, the Absolute helped me to understand "freshness" and what can happen when heat doesn't enter the process, but the "Heart" still has me confused. I understand that it is only part of the Peppermint, but how it can small like burning electronics, which has its own strange kind of appeal, amazes me.

It is very difficult to remember and describe smells as our vocabulary for this is so poor. We have very few words (in English, other languages may be better at this) which directly describe a smell, and most of them are negative, such as "stench", or "stink". Even the word "smell" can have a negative connotation. So, in attempting to describe a smell it is necessary to use adjectives which are usually used to describe other senses. Colour, and vision is an obvious one. "Smells like cut grass", "Smells Green". Sensations can help, "I think it smells hot/cold". Taste, " it smells sweet/bitter/ salty". And, definitely, texture. "This smells powder/ dry, oily, greasy". Smells need all the help they can get (or you do, who is trying to learn them), anything that makes your remembering better can and should be used.

A fractionated oil has been separated into component chemicals by further distillation. You can separate any oil into Top, Middle and Base chemicals, by controlling the time at which the components are captured. Essential oils contain many, many chemicals, each one smelling (slightly) different, each one contributing to the overall smell of the oil. It is possible to isolate one, or a small mixture of those components. This is often done, for a variety of reasons.
 

David Ruskin

Well-known member
May 28, 2009
When you distill a mixture of chemicals, you can follow the progress of separation as the individual chemicals vaporise and pass over into the condenser. It is possible to isolate specific chemicals this way. You mentioned Peppermint oil; untouched, simply distilled Peppermint oil will be solid because of the amount of Menthol present. The liquid oil we are familiar with has had some of the Menthol removed to allow for it to remain liquid. The Menthol left over, is a fraction of Peppermint oil used on its own.
 

Jim Conti

Member
Jun 22, 2016
Ah, that's interesting, so even some of the things that we think of as "pure" essential oils are fractionated!

As long as they put that menthol in Vicks VapoRub I'm happy. I love Vicks VapoRub!

Thank you!
 

PerfumerSupplyHouse

Ingredients Supplier
Basenotes Plus
Dec 20, 2013
When you distill a mixture of chemicals, you can follow the progress of separation as the individual chemicals vaporise and pass over into the condenser. It is possible to isolate specific chemicals this way. You mentioned Peppermint oil; untouched, simply distilled Peppermint oil will be solid because of the amount of Menthol present. The liquid oil we are familiar with has had some of the Menthol removed to allow for it to remain liquid. The Menthol left over, is a fraction of Peppermint oil used on its own.

Just a tiny clarification, Peppermint Oil (mentha piperita) actually only contains about 35-40% menthol and the crude oil is a liquid. The variety of mint oil that menthol is obtained from is Cornmint (mentha arvensis). That one has about 80% menthol and once it is removed, the remaining oil is called DMO (dementholized mint oil).
 

Jim Conti

Member
Jun 22, 2016
When I was a little kid I used to like to compare the different mint varieties of Lifesavers - pepOmint, spearOmint, and wintOgreen. I remember thinking that peppermint was too spicy hot. I really liked wintergreen but if I ate too many I got nauseated. (There was also that spark in the dark trick.) But my favorite desert island mint flavor was spearmint. Cool, green, lush and refreshing! I loved those spearmint green jelly leaves on my grandmother's coffee table. There was always mint in the iced tea' growing like a weed in the neighbor's garden. I preferred Wrigleys Spearmint gum over their DoubleMint. I wonder why mint never crossed over to personal and household fragrance products, other than toothpaste and mouthwash?
 
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David Ruskin

Well-known member
May 28, 2009
Just a tiny clarification, Peppermint Oil (mentha piperita) actually only contains about 35-40% menthol and the crude oil is a liquid. The variety of mint oil that menthol is obtained from is Cornmint (mentha arvensis). That one has about 80% menthol and once it is removed, the remaining oil is called DMO (dementholized mint oil).

Thank you for that, I always like to learn things. I really thought that Menthol came from Peppermint. So can you tell me why my Olbas oil contains both Dementholated Peppermint oil, and added Menthol?
 

David Ruskin

Well-known member
May 28, 2009
When I was a little kid I used to like to compare the different mint varieties of Lifesavers - pepOmint, spearOmint, and wintOgreen. I remember thinking that peppermint was too spicy hot. I really liked wintergreen but if I ate too many I got nauseated. (There was also that spark in the dark trick.) But my favorite desert island mint flavor was spearmint. Cool, green, lush and refreshing! I loved those spearmint green jelly leaves on my grandmother's coffee table. There was always mint in the iced tea' growing like a weed in the neighbor's garden. I preferred Wrigleys Spearmint gum over their DoubleMint. I wonder why mint never crossed over to personal and household fragrance products, other than toothpaste and mouthwash?
I can never understand the popularity of Wintergreen as a flavouring in America. It reminds me only of mouthwash and the dentists. Ain't different cultures great!
 

Jim Conti

Member
Jun 22, 2016
It's also used in root beer soda along with other flavorings. I'm not sure if it's in cola sodas or not. It does have a sort of medicinal taste and I think that was how it started. It's supposedly toxic in enough quantity and 1 ounce is equivalent to almost 2 ounces of aspirin! So I guess you could drink root beer for a headache...

Olbas...I love that stuff!
 

David Ruskin

Well-known member
May 28, 2009
Oh and I forgot, Deep Heat vapour rub, for strained muscles. Guess it's less toxic than Sassafras , but tasted not much better. It has to be a cultural thing but I hate root beer, and don't get me started on Dr. Pepper.
 

PerfumerSupplyHouse

Ingredients Supplier
Basenotes Plus
Dec 20, 2013
Thank you for that, I always like to learn things. I really thought that Menthol came from Peppermint. So can you tell me why my Olbas oil contains both Dementholated Peppermint oil, and added Menthol?

I've never heard of Olbas Oil, but I imagine it is because DMO and Menthol are more widely (commercially) available than the whole Arvensis oil. In fact, I think 99% of the mentha arvensis grown is used for nat menthol production, since the demand is so great.

One other side note (sorry this is going pretty deep), but the Indian manufacturers (I represent one) who offer mint and menthol call the DMO "dementholated or dementholized peppermint", when in fact it isn't peppermint at all. It's just a bad habit they got into years ago.
 

David Ruskin

Well-known member
May 28, 2009
Maybe Olbas oil is unique to the UK. It is a mixture of Essential oils (including Clove, Eucalyptus, Peppermint and Cajeput. This is the only time I have ever encountered Cajeput oil in fragrance) which can be used when you have a head cold as it helps unclog a clogged nose. Apparently it can also be used as a muscle rub, although I have never done that.
 

pkiler

Basenotes Plus
Basenotes Plus
Dec 5, 2007
I use Cajeput oil as a topnote for some bases. Similar to Eucalyptus, but a slightly different profile. That profile matched some missing elements to a GC of a flower I have been working on. Plus, we have it in house because my wife from Indonesia does in fact use it for chest and muscle rubs. I buy it in retail bottles when we travel to Indonesia.

Kayu Putih / Cajeput EO

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julian35

Basenotes Plus
Basenotes Plus
Feb 28, 2009
Oh and I forgot, Deep Heat vapour rub, for strained muscles. Guess it's less toxic than Sassafras , but tasted not much better. It has to be a cultural thing but I hate root beer, and don't get me started on Dr. Pepper.

David, Birch Beer is also a lovely drink here. You would not like it I am guessing with it's strong wintergreen.
You comment reminded me of that singing ad for Dr. Pepper. "I'm a Pepper, you're a Pepper, wouldn't ya like to be a Pepper too!" Apparently not. LOL
 

David Ruskin

Well-known member
May 28, 2009
David, Birch Beer is also a lovely drink here. You would not like it I am guessing with it's strong wintergreen.
You comment reminded me of that singing ad for Dr. Pepper. "I'm a Pepper, you're a Pepper, wouldn't ya like to be a Pepper too!" Apparently not. LOL

I remember the first (and only) time I tasted Dr. Pepper. I took a mouthful, and spat it out.
 

Bill Roberts

Well-known member
Mar 1, 2013
As I happened upon this in a websearch for Robertet VETIVER HAITI VETIVEROL FRACTION OIL and saw a statement that can easily mislead, I wished to add something.

The above speaks of vetiver oil containing "50% vetiverol" and while that may not have been the author's intent, on ordinary reading a person would think there is a particular material vetiverol, such as there is patchoulol, geraniol, ambrinol, cedrol, etc, and likewise there is a specific material vetiveryl acetate, as there is patchoulyl acetate, geranyl acetate, etc.

Those are not the case, and not simply from isomers.

In the case of vetiver, the "-ol" refers only to being a mixture of quite different alcohol materials, not a specific one.

In the Essential Oils University Database, for example, one will find a single (mistaken) entry for Vetiverol, but for all other Vetiver analyses, one sees large numbers of varying alcohols in vetiver, none of them named vetiverol.

Vetiverol is instead of a particular substance, a mostly-alcohols distilled fraction of vetiver essential oil, and vetiverol acetate is an acetylated product of that. Both are very complex mixtures.
 
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Bill Roberts

Well-known member
Mar 1, 2013
i don't know. I really have not compared, both to me have good tenacity. On whether it would be expected, on the one one hand alcohols have considerably more intermolecular attraction to each other thanks to hydrogen bonding, but on the skin they are interacting mostly with other materials rather than themselves, and the skin itself is fairly lipophilic, whereas of course the acetates have greater molecular weight. Certainly too much going on for me to genuinely figure out.

TGSC gives lower vapor pressure for vetiveryl acetate than for vetivol, though. Of course the vapor pressure figures there are not tremendously reliable.

I would say both have good but ordinary tenacity for base notes, and not the super tenacity you have been seeking.
 

Bill Roberts

Well-known member
Mar 1, 2013
For fun, and as illustration is better than broad claim only, from a Phytochemia analysis here are what they consider the key materials they are looking to find in Vetiver, and the amounts found in a particular Indonesian batch offered by Plant Therapy and considered of a "woodsmoke" type. Alcohols in bold

β-VETIVENENE 6.6
KHUSIMOL 6.2
ZIZANOIC ACID 4.2
γ-VETIVENENE 3.5
β-VETISPIRENE 2.4
α-AMORPHENE 2.4
β-VETIVENENE ISOMER I 2.2
EPIZIZANOIC ACID 2.1
δ-AMORPHENE 2.0
NIGRITENE 1.9
β-VETIVONE 1.8
PREZIZAENE 1.8
KHUSIOL 1.7
ZIZANOL 1.7

α-VETIVONE 1.6
β-VETIVENENE ISOMER II 1.5
α-VETISPIRENE 1.4
ISOVALENCENOL 1.4
VETISELINENOL 1.4

(Z)-ISOVALENCENAL 1.1
EPI-ZIZANONE 1.1
KHUSIMENE 1.0
6-EPI-NIGRITENE 1.0
CYCLOCOPACAMPHA-12-ol (epimer A) 1.0
EREMOPHILA-1(10),7(11)- DIENE 1.0

There were no other alcohols shown as present at 1% or more. However, over 36% of the sample remained unidentified, so collectively other alcohols below 1% each might sum to quite a bit.

In contrast, here is an EB Vetiver Haiti, having (E)- ISOVALENCENOL at 10.77 % and KHUSIMOL at 8.38%.
 

mnitabach

Well-known member
Nov 13, 2020
That GCMS of the Eden Haiti organic vetiver is very interesting, as it's a really nice material IME. One thing I'm a bit confused by is that the total of the listed percentages is nowhere even approaching 100%. That means that there are peaks at molecular weights that can't be identified as known molecules? Do we know if any of them are relevant to the odor? Also, one of the nice things about this particular vetiver is it has a nice pretty prominent orangey citrusy facet. Do any of these identified constituents have such an odor facet?
 

Bill Roberts

Well-known member
Mar 1, 2013
EB often provides CoA's that don't provide anything like everything the GC/MS would have turned up, but only enough to show "yes, it's characteristic."

I definitely don't know on the components!

Vetiver is one of those things I very much like to have fractionated down to fine detail.

Actually that, although not so fine in detail, was what I was searching for, as Robertet does have a fractionated vetiver. It would still have very many components, but I highly expect it's a fine perfumery material.

I also may get to put into practice xii's paper chromatography technique, if I can get suitable "paper" (which might literally be paper.)

I am even thinking the paper strips could have their portions recovered from them with alcohol wash. Why not?

Inefficient probably, and hardly suitable for large scale, but for the hobbyist why not?

And I am not going to do it, or not anytime soon anyway, but of note, it's possible to way overload a silica column and still get some useful separations sometimes. In other words, one could have a modest diameter silica column and load it up with at least 10 g of vetiver oil, perhaps even 30 g, and different parts of it will still elute at different times, just with much less resolution when reasonably loaded.
 

Bill Roberts

Well-known member
Mar 1, 2013
Very interesting, thank you!

And lastly, while on the sidetrack here of fractionation: I have not yet done it with aromamaterials, but I had a period of putting a lot of trouble into separating nutraceutical materials simply with partitioning.

As an example, you add say 50 mL each of say methanol and n-hexane (not mixed hexanes) to a separatory funnel together with your material, shake, and separate the layers. Put this aside.

Now take the methanol layer and partition again against hexane. Set aside the hexane layer separately from the first.

Repeat one more time, but this time, combine the hexane layer with your second one.

Now take the hexane layer and follow similar process, but this time it is methanol layers being put aside.

After all this, remove the solvent from the final methanol layer from the first set of steps. This material "survived" three methanol/hexane partitionings and therefore the great majority of it must be material considerably more soluble in methanol than in hexane.

Then remove the solvent from the final hexane layer. Ditto, except this will be rich in material much more soluble in hexane than in methanol.

And finally, combine the other parts which sometimes partitioned out in the methanol layer and sometimes in the hexane. This will be mostly material with not wildly different solubilities in methanol and hexane.

Now I had good luck with the materials I was wanting to get. Perhaps aromamaterials might all want to wind up in one layer or the other and there would be no separation, but I am thinking it's possible one might be able to separate say alcohols from terpenes, and generally more polar from less polar materials in this manner, and it's quite easy to do.

Further, one might have materials which didn't separate in some other way, for example distillation, but which will separate this way.

That is not the only solvent pair possible but it's a good illustration. Illustrated largely because potentially relevant to fractionating vetiver, and because I literally have never seen this method anywhere anytime*, so it is not that everyone would have access to it already.

* Countercurrent separation is fundamentally the exact same process, just far more sophisticated, but involves uber-expensive equipment and works with only tiny amounts.

/sidetrack
 

Bill Roberts

Well-known member
Mar 1, 2013
Lastly (from me) the vetiver alcohols from a Vetiver Haiti reported on EODB:

Khusimol 14%
beta-Eudesmol 4%
trans-Eudesma-4(15),7-dien-12-ol (2 epimers) 3.5%
Eremophila-1(10),7(11)-dien-2alpha-ol 3.2%
Eudesm-6-en-4beta-ol 3.1%
(E)-Eremophila-1(10),7(11)-dien-12-ol 3% (Isovalencenol)
Spirovetiva-3,7(11)-dien-12-ol 3%
alpha-Bisabolol 1.5%
Eudesma-3,5-dien-1alpha-ol 1.2%
alpha-Eudesmol 1%
beta-Bisabolol 1%
10-epi-gamma-Eudesmol 0.9%
1-epi-Cubenol 0.9%
Junenol 0.8%
Preziza-7(15)-en-12-ol 0.75%
Eremophila-1(10).4(15)-dien-2alpha-ol 0.75%
Eudesm-4(15)-en-5beta-ol 0.7%
12-nor-Ziza-6(13)-en-2alpha-ol 0.7%
Ziza-6(13)-en-3beta-ol 0.6%
Cyclocopacamphan-12-ol (epimer B) 0.5%
Amorph-4-en-10-ol (epimer B) 0.5%
Eremophil-7(11)-en-10beta-ol 0.5%
Eudesma-4(15),7-dien-2beta-ol 0.5%
(E)-Opposita-4(15),7(11)-dien-12-ol 0.5%
Cascarilladienol 0.4%
Bisabola-3(15),10-dien-7-ol 0.4%
6-epi-alpha-Bisabolol 0.3%
cis-Eudesm-6-en-11-ol 0.3%
Amorph-4-en-10-ol (epimer A) 0.3%
Cyclocopacamphan-12-ol (epimer A) 0.3%
Khusian-2-ol 0.3%
Valerianol 0.2%
Pogostol 0.2%
Intermedeol 0.2%
10-epi-Cubenol 0.2%
6-epi-Shyobunol 0.2%
Prezizan-7beta-ol 0.2%
Eudesma-4(15),7-dien-3beta-ol 0.2%
Ziza-6(13)-en-3alpha-ol 0.2%
beta-Funebren-14-ol 0.2%
Preziza-7(15)-en-3alpha-ol 0.2%
7,11-Epoxy-eremophila-1,9-dien-8alpha-ol 0.2%
beta-Elemol 0.1%
cis-Guai-6-en-10-ol 0.1%
4,7-Epoxy-spirovetiv-2-en-11-ol 0.1%
Guaia-1(5)-dien-3alpha-ol 0.1%
Helifol-1-en-14-ol 0.1%
cis-Eudesma-6,11-dien-3beta-ol 0.1%
Eremophila-1(10),11-dien-2alpha-ol 0.1%


A much better example of how complex a material Vetiverol is!

(And on top of this, a Vetiverol product won't be absolutely only the alcohols.)

Btw, the compound mentioned in the article you provided a link for, 2-epi-ziza-6(13)-en-3-one, was present at 0.2% in that sample.

Saying the obvious, while that doesn't sound like much, if something has say 100 times the odor intensity of the other materials in a sample, 0.2% could be very significant.
 
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Big L

Well-known member
Nov 23, 2019
And I am not going to do it, or not anytime soon anyway, but of note, it's possible to way overload a silica column and still get some useful separations sometimes. In other words, one could have a modest diameter silica column and load it up with at least 10 g of vetiver oil, perhaps even 30 g, and different parts of it will still elute at different times, just with much less resolution when reasonably loaded.

I might be stating the obvious, but should one attempted to do it, it is possible to achieve high loading capacity, together with high resolution, by using an optimized step gradient.
 

Bill Roberts

Well-known member
Mar 1, 2013
Pretty good loading seen here: http://www.flash-purification.com/how-to-efficiently-scale-up-flash-column-chromatography/

I have sadly only ever had access to gravity chromatography, as it's all my professor used in his lab (obviously, chromatography wasn't the focus, the preference was for the syntheses themselves to give good purity and then for crystallization to suffice) and I never bought flash chromatography equipment for myself. I always had to limit loadings, I forget to what, but it sure didn't seem efficient.

5% would not be a bad loading at all.
 

Bill Roberts

Well-known member
Mar 1, 2013
Ziza-6(13)-en-3alpha-ol is a synonym for 2-epi-ziza-6(13)-en-3-one?

No, I trimmed the non-alcohols from the above list as I was wanting to show only the alcohols. The 2-epi-ziza-6(13)-en-3-one amount is within the same GC/MS as above. The entire thing can be found on the EODB. Unfortunately the analyses don't have web links so you just have to search for vetiver or for that compound.
 

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