Chemical constituents of Gardenia fragrance

parker25mv

Well-known member
Oct 12, 2016
Gardenia has highly fragrant white flowers. In the evening, the opening buds smells slightly green and piquant — the salicylate aspect. The flowers also smell creamy or lactonic, recalling coconut and peach skin. There is an unmistakably heady indolic element of jasmine. In ripe blooms, they have a sharp green or ‘mushroom’ overtones, almost acerbic. Additionally, gardenias share their floral aspects with lily, lily of the valley, ylang ylang, and a bit of rose.

Creating an accurate imitation of gardenia has remained elusive, but I believe that may simply be due to a lack of understanding of the full profile of chemical constituents that give gardenia its characteristic fragrance.

According to one study, the main compounds in headspace of fresh Gardenia flower included farnesene(64.86%), cis-ocimene(29.33%), linalool(2.74%), cis-3-hexenyl tiglate(1.34%), methyl benzoate(0.25%).

A headspace analysis of the endangered Hawaiian species Gardenia brighamii showed that its gas-phase components contains 41% methyl benzoate, 13% (3Z)-hex-3-enyl benzoate, 7% indole that recalls ‘white-flower smell’, 7% jasmine lactone that lends the jasminic and coconut touch, and 3.7% (3Z)-hex-3-enyl tiglate that gives the tang of soil fungi and mushrooms to the flower.

Lets take a look at some of these chemical constituents.

alpha-Methylbenzyl acetate is only found in nature in gardenia flowers and, indeed, the fragrance of this chemical bears more than a passing resemblance to gardenia.
Common synonyms include 1-Phenyl ethyl acetate, styrallyl acetate, gardenol, and methylph*enylcarbinyl acetate. It can be synthesized from acetophenone, by reduction to the corresponding alcohol and then formation of the ester. (Acetophenone, by the way, is reputed to smell wonderful, described as something like orange blossom with a bit of artificial cherry/almond)

It appears that the particular constituent of gardenia is β-cis-Ocimene, but here is some fragrance information I was able to find about some other ocimenes, perhaps this will help us garner a fuller understanding of the type of scent qualities in this family:

α-Ocimene has a medium strength, fruity, floral aroma with a wet cloth note. It is contributor to green odor of unripe mango and of mango ginger (Curcuma amada). It is used in oriental pickles.

β-Ocimene has a medium strength, tropical, green, terpy and woody odor with vegetable nuances. It is used as a flavoring agent where it has a green, tropical, woody flavor with floral and vegetable nuances. It is a flavor and fragrance additive as well as a common component in many essential oils.

β-cis-Ocimene has a medium strength, warm, floral, herbal, sweet, citrus-like aroma. It is a component of the chemical communication system of the tea weevil and cotton bollworm.

trans-β-Ocimene, synonym (E)-ocimene, was found to be the major chemical component in the headspace of Lilac, although not the most characteristic component.
(the fragrance of Lilac also contains small quantities of indole, like gardenia)

The fragrance of Lily also contain cis-ocimene, linalool, and methyl benzoate, which explains the fragrance resemblance to gardenia.

If Lily of the Valley bears some resemblance to gardenia, perhaps it is because it contains farnesol, which is chemically similar to farnesene but with a hydroxyl group, basically the corresponding alcohol to this terpene.

Linalool is the most important chemical component of lavender oil, which contains up to 35% linalool and 40% linalool acetate.

further reading of interest:
http://www.bojensen.net/EssentialOilsEng/EssentialOils13A/EssentialOils13A.htm
http://www.bojensen.net/EssentialOilsEng/EssentialOils17/EssentialOils17.htm
http://www.bojensen.net/EssentialOilsEng/EssentialOils16/EssentialOils16.htm

Indole: Why is a Compound That Smells Like Feces Put in Perfume?
 

parker25mv

Well-known member
Oct 12, 2016
Styrallyl Acetate

Odour type is green with a medium odour strength, recommended smelling in a 10% solution or less. Described as green, leafy, gardenia, rhubarb and musty.

Not obviously floral on first sniff, this is an essential ingredient in Gardenia accords and a great modifier in many floral compositions. Widely used but never in very high proportions.

Styrallyl acetate has a dry, intense, green, floral odour reminiscent of gardenia. It is a key ingredient in gardenia, tuberose and other flowery perfumery compositions. Styrallyl acetate is also used in many other blossom compositions, in particular to add dry top notes.

https://hermitageoils.com/product/styrallyl-acetate/
 

I.D.Adam

Well-known member
Nov 14, 2014
I disagree that the gardenia scent has not been well reproduced in fragrance. There are many commercial fragrances with very nice gardenia scents done by competent perfumers. And while headspace analysis and GC/MS can give insight as to what components make up the scent of a given object, they are notoriously inaccurate when translated on a percentage basis in recreating the true scent. That is best done by an experienced perfumer familiar with the behavior of scent compounds as a blended fragrance does not give off scent in the same way a plant does.

In your blending experience have you come across a particularly good formula that recreates gardenia?
 

parker25mv

Well-known member
Oct 12, 2016
Although Arctander says “it is conventionally classified as a Gardenia-green material, but its odor is typical only of certain stages of maturity of the Gardenia flower, and only of certain species. However, the ester finds use in numerous fragrance types, mostly those including fruity and green notes”. I believe that while gardenol (Styrallyl Acetate) has a very characteristic odor of gardenia fragrance, it’s also a very minor component of gardenia fragrance. Supposedly, in too high of a concentration it can smell harsh and unpleasant.
 
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pkiler

Basenotes Plus
Basenotes Plus
Dec 5, 2007
I disagree that the gardenia scent has not been well reproduced in fragrance. There are many commercial fragrances with very nice gardenia scents done by competent perfumers. And while headspace analysis and GC/MS can give insight as to what components make up the scent of a given object, they are notoriously inaccurate when translated on a percentage basis in recreating the true scent. That is best done by an experienced perfumer familiar with the behavior of scent compounds as a blended fragrance does not give off scent in the same way a plant does.

In your blending experience have you come across a particularly good formula that recreates gardenia?

Seems that most/all gardenia accords that we have are pretty terrible. That's why I'm building my own. And it's not just the green fresh topnotes, but the base needs serious consideration too. It's quite a challenge, requiring a new toolbox. I've acquired many new materials for it.
 

parker25mv

Well-known member
Oct 12, 2016
I'm not sure there's a need to replicate the exact fragrance profile of gardenia in its entirety. Indeed, there are some aspects of gardenia smell that may not be so desirable, depending on personal tastes. Maybe focus on those elements in the natural fragrance that are most desirable. What is it about gardenia, exactly, that is so wonderful and distinctive? Focus on that. Of course there needs to be some other background notes as well (however generic they may be), and this could probably be accomplished with other floral essential oils.
 

parker25mv

Well-known member
Oct 12, 2016
Seems that most/all gardenia accords that we have are pretty terrible.
That definitely seems to be the consensus among perfume connoisseurs, but you know, from various online research I've done, it seems like Yves Rocher Pur Desir de Gardenia (which has sadly now been discontinued) captured the exact fragrance of gardenia. It wasn't expensive either. So it is possible to formulate it.
 

parker25mv

Well-known member
Oct 12, 2016
Interesting blog I thought I would share with you:

" I think I've had more requests for a natural Gardenia scent than for anything else over the years...and up until now I've had to say 'It can't be done'. [...]
It's such an amazing scent, deep, fresh, tangy, musky and with something else that is totally mysterious there in the background as well. The Gardenia flower has a potent hypnotic magic about it that is impossible to copy.
There are many gardenia perfumes on the market, and each of them focuses on a different aspect of this magic. But none (to my nose anyway) come anywhere near the real thing. (Of course, few, if any of them actually contain real gardenia, so I suppose it's not really that surprising)...Then, a few months ago, I got hold of some real Gardenia absolute from a lovely supplier in Europe. It takes literally thousands of kilos of Gardenia petals to create just one kilo of Gardenia absolute. [...] The absolute itself arrived and I excitedly opened the bottle:
The first impression was dissapointing. It's undeniably Gardenia, but somethow in the extraction process, the deep, sexy, sultry and musky flower scent comes through, but the magical fresh top notes that make sniffing a freshly picked gardenia flower so mesmerizing, went astray.
I put it on the backshelf for a while, and then (after yet another request for a Gardenia perfume...) I pulled it back out and set out to recreate the elusive top notes I remembered so well from my Grandmothers garden....
I experimented with a number of related flowers, and discovered that many of the white flowers have similar notes to them! Mother Nature seems to marry the creamy white colur in nature to specific scent notes, so by carefully adding just touches of a variety of these, plus some fresh leafy green notes to give the feeling of that newly picked fresheness you get from the crushed stem and leaves and oh my goodness, there it was, the scent I so remembered from early dew covered mornings in my grandmothers garden in Australia....
My mother was the first to try it...she's an avid Gardenia lover with a very accute sense of smell and one of my hardest critics...I sprayed some on her wrist when she popped by that afternoon without telling her what it was and "Oh my, Gardenia! How beautiful!"
The only problem was that the scent faded quickly, just like the natural scent of the flowers will once you bring them indoors....
So from there I spent some further months finding a gentle base note that would hold and extend the glorious fragrance without distracting from the gardenia accord itself.... "

http://perfumebynature.blogspot.com/2010/05/musings-on-gardenia.html

The blog was written by an old member of this forum, Ambrosiawomble.
 

parker25mv

Well-known member
Oct 12, 2016
I might be wrong, but I was thinking Hinoki (Japanese Cypress) oil would go well with gardenia, as a mild base note.
might also help contribute to the terpene citrusy smell that's so important in the scent of gardenia (although you wouldn't want to rely all on this)
 

parker25mv

Well-known member
Oct 12, 2016
Ok, got a sample of some alpha-Methylbenzyl acetate and can tell you what it smells like.

The first impression, it smells like burnt plastic, chemical-like, somewhat like nailpolish remover, with a little tire rubber. Trying to smell more carefully, it smells a bit ethereal like lilac, there’s an aspect to the smell that’s very distantly like grapefruit but not the same, the nailpolish aspect smells very perfume-like, possibly floral, kind of sweet. It’s very potent, like overconcentrated jasmine. There’s something a little bit similar to honeysuckle. It does smell a little like part of the gardenia fragrance, not in an unnatural way. I think I'm going to have to agree with Actander when he says "its odor is typical only of certain stages of maturity of the Gardenia flower". It kind of smells like it might be one of the smaller fragrance notes within the overall fragrance of gardenia. By itself, it's only distantly reminiscent of gardenia, but there's something unique to it that's very specific to gardenia.

Not sure that I can recommend this for perfume. If it is used, it's probably going to be in extremely small concentration, only to accentuate other notes. With the way this smells, I'm not even sure it's an essential to synthetic gardenia fragrance.
 

Dmitriy

Well-known member
Dec 10, 2014
That definitely seems to be the consensus among perfume connoisseurs, but you know, from various online research I've done, it seems like Yves Rocher Pur Desir de Gardenia (which has sadly now been discontinued) captured the exact fragrance of gardenia. It wasn't expensive either. So it is possible to formulate it.

I have a half bottle Yves Rocher "Pur Desir de Gardenia" and I agree that this perfume is more closely to smell of the living flower that I met. I am also a big fan of gardenia and keep as a sample this perfume then to try to ever build my own perfume. )) :smiley:
 

jfrater

Well-known member
Jun 2, 2005
Seems that most/all gardenia accords that we have are pretty terrible. That's why I'm building my own. And it's not just the green fresh topnotes, but the base needs serious consideration too. It's quite a challenge, requiring a new toolbox. I've acquired many new materials for it.

Arcadi Boix Camps has a gardenia called gardenia storm. It is simply outstanding. It can be used as a single gardenia or as an enhancer in pretty much everything. I recommend you get some. He also has Gardenia Blanc which is less expensive but also amazing. These two bases are true gardenia.
 

jfrater

Well-known member
Jun 2, 2005
Although Arctander says “it is conventionally classified as a Gardenia-green material, but its odor is typical only of certain stages of maturity of the Gardenia flower, and only of certain species. However, the ester finds use in numerous fragrance types, mostly those including fruity and green notes”. I believe that while gardenol (Styrallyl Acetate) has a very characteristic odor of gardenia fragrance, it’s also a very minor component of gardenia fragrance. Supposedly, in too high of a concentration it can smell harsh and unpleasant.

Jean Carles used 4% of Styrallyl acetate in Ma Griffe - it is absolutely beautiful and unique. He coupled it with 1% citronella oil (rarely used these days because of its use in domestic cleaning products).

The main character of Ma Griffe is styrallyl acetate+citronella.
 

parker25mv

Well-known member
Oct 12, 2016
Ok, I can comment a little bit more, 2 hours after the sample has been allowed to evaporate on the test strip. The burnt plastic/rubber smell still does not fully go away even after diffusion, but the floral element does shine through a little bit more. What the nail polish odor really reminds me of is model airplane glue. It smells sweet, floral, and sharp very much like artificial plum fragrance. The smell has a "green" aspect but it's a harsh green smell. It's "sharp" in the same sort of way vinegar has a sharp smell. The same "burnt plastic" aspect turns itself into part of the deep cloying (almost musky but different) element of gardenia. The floral aspect of the smell is in a strange twilight zone halfway between rose oxide and orange flower ether (or grapefruit). When I said it smelled kind of like honeysuckle, I mean the small sharp cloying character note in honeysuckle fragrance. To summarize, this isn't really the part of gardenia I want to smell.
 

parker25mv

Well-known member
Oct 12, 2016
I wanted to point something else out that's kind of interesting from a chemical perspective. Rose acetate (i.e. Rosone) is basically just the chlorinated version of Styrallyl Acetate (i.e. alpha-Methylbenzyl acetate).

(obviously rose acetate is not a naturally-occurring chemical, but it is commonly used by in by perfumers in rose compositions)


Another olfactory connection I noticed, I happened to leave some pomelo (citrus fruit) rinds out on a plate for a few days, and when I came back and took a smell, I happened to notice a very familiar and pronounced olfactory note: it was the same smell as styrallyl acetate. This smell isn't how the rinds smell fresh, but once you leave them around a little while the smell somehow seems to "shift" towards this direction. (It's not really a good smell but it's not a bad one either)
I would guess the fragrance similarity probably has something to do with the fact that alpha-terpinyl acetate is part of the fragrance profile of pomelo and is structurally similar to styrallyl acetate, just one more methyl group.
 
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David Ruskin

Well-known member
May 28, 2009
I wanted to point something else out that's kind of interesting from a chemical perspective. Rose acetate (i.e. Rosone) is basically just the chlorinated version of Styrallyl Acetate (i.e. alpha-Methylbenzyl acetate).

(obviously rose acetate is not a naturally-occurring chemical, but it is commonly used by in by perfumers in rose compositions)
And the two smell nothing like each other. What is your point?
 

Black Sheep

Member
Jan 3, 2011
Arcadi Boix Camps has a gardenia called gardenia storm. It is simply outstanding. It can be used as a single gardenia or as an enhancer in pretty much everything. I recommend you get some. He also has Gardenia Blanc which is less expensive but also amazing. These two bases are true gardenia.

Really old thread, I know but is it even possible to purchase anything from this gentleman any longer? I know there was an email for him and I did email him to no avail. I've heard he can be very difficult.
Well, just asking since I'm working on a gardenia accord and jotted down some of the formulas that are here in the forum to work on. Not looking to make a magnificent accord but get practice with this flower.
 

pkiler

Basenotes Plus
Basenotes Plus
Dec 5, 2007
Difficult to get response from him, possibly Jamie and myself might be able to get response and make a purchase.

Ever since Russia stole Crimea, Arcadi's business has been much more difficult.
 
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mattmeleg

Well-known member
Aug 14, 2017
Honestly, there`s no such thing as a specific "gardenia," scent.
Ever smell oneearly in it`s life span? It`s green and fresh.
Smell it when it`s turning brown...a LOT more indole.
Smell in the morning, very different from at night.

One could spend their entire life making various versions of a gardenia perfume.

Sometimes they smell nothing like flowers,
Like that blue paste dentists shoot into your mouth, PURE wintergreen or medicine.... BLAH!
 

Black Sheep

Member
Jan 3, 2011
Honestly, there`s no such thing as a specific "gardenia," scent.
Ever smell oneearly in it`s life span? It`s green and fresh.
Smell it when it`s turning brown...a LOT more indole.
Smell in the morning, very different from at night.

One could spend their entire life making various versions of a gardenia perfume.

Sometimes they smell nothing like flowers,
Like that blue paste dentists shoot into your mouth, PURE wintergreen or medicine.... BLAH!

Gardenias on the verge of decaying smell the best, IMO.
I love smelling them in bowls of water in our house. Next month is when all the bushes bloom for 1 month only.

One of the best renderings of gardenias decaying is/was Tom Ford Velvet Gardenia. A very beautiful, beautiful scent.

I'd want to create something akin to decaying gardenias, I believe.
 

parker25mv

Well-known member
Oct 12, 2016
I get a sweet tea smell from the gardenia variety 'Crown Jewel' (a cold hardy hybrid variety). Some 4-Oxoisophorone (ketoisophorone, pretty commonly available) might be useful here.
This variety also seems to have a little bit more fruitiness than the standard gardenia.
 

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