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Tuesday, May 18, 2010

Indole & Jasmine: Indolic vs. Non-Indolic or Dirty vs.Clean

Say the word jasmine among perfume circles and expect to see the characterisation of indolic being brandished a lot at no time. Expect to see upturned noses with "indolic" mentioned alongside "fecal" in the same breath. Is jasmine a "dirty" word? Who potty-trained it? These thoughts evolved in our mind as we re-examined the troubled relationship of perfume lovers to the perfumery "king of flowers", especially now that the weather is warm and jasmine vines are flowering like mad; and so decided to take things at the top.

Indole is often used as the scapegoat for "stinky" smells, but the truth is somewhat different. Originally indole is a portmanteau of the words "indigo" and "oleum", because the chemical substance named indole was first isolated by treatment of the indigo dye with oleum (oil), thus giving rise to indole chemistry.
Indole is an aromatic heterocyclic organic compound which contains a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring (don't worry if you're not great at chemistry, it will all make sense in a second); thus compounds which contain an "indole ring" (sequence of molecules) are accordingly named "indoles".  

What does this mean? It smells "weird". But not necessarily of feces or poop, contrary to common knowledge! Organic chemistry on the whole isn't averse to naming names quite literally, especially when it comes to foul-smelling components: Hence we have cadaverine (for cadaver smell), putrescine (for the stench of garbage), skatole (from the Greek σκατό, litterally meaning shit), or butyric acid (the smell of rancid butter from the Greek βούτυρο/butter). No, the nomenclature of organic chemistry is pretty much to the point, which would pose serious doubts as to why leave such an appropriate scent out there with no fitting baptism!

The answer is simple: Pure indole, the one which is indeed present in feces and also in small part present in white flowers (such as jasmine, gardenia, tuberose and orange blossom; but also in honeysuckle and lilac, technically non white) doesn't really smell of poop in isolation. The white crystals of indole (mainly derived from coal tar) contribute to the effect, in tandem with other things (surely both feces and flowers contain myriads of molecules) but not in seperation so much. Isolated indole has a musty, weird moth-ball smell that is a little stale, reminiscent of decay, like something has gone off and you can't really pinpoint what it is. In presence of humidity and musky compounds it can become a little much, reminiscent of the ambience of a...toilet. In a way an "Eros & Thanatos" concept.
It's interesting to note that a common derivative is the amino acid tryptophan, calming neurotransmiter serotonin's percursor and an essential amino acid in the human diet. (It's isolated in caseine which is found in dairy products, but also in chocolate, oats, poultry, pumpking seeds, peanuts, spirulina and several others. Makes seeing food in a whole different way!).

But should the smell direct us into seperating white floral and jasmine fragrances into naturally-derived or not? In short, does an indolic scent indicate we're dealing with a fragrance containing natural jasmine? The answer isn't as easy as all that. It's true that natural jasmine essence, as used in the perfume industry, is dark and narcotic, containing about 2.5% of pure indole. This often gives a "full", lush and intimate ~some say naughty~ effect in the finished compound, making the jasmine "sexier" or "animalic" as described by perfume enthusiasts (the naughty effect is more due to paracresol, reminiscent of horses' smell). Try Serge Lutens' A la Nuit, also his Sarrasins (a different treatment of intimate) or Montale Jasmine Full, and you know what I am talking about. Olene by Diptyque is another one which has a dubious intimate ambience (described by someone as "one bad mama jama of a jasmine"), as does the extrait version of Joy by Jean Patou, sublimated in rosy and musky tones as well, and the heart of Bal a Versailles (flanked by naughty civet). Also try Bruno Acampora Jasmin. However you don't necessarily have to tread on jasmine to get copious amounts of indole either: Try a carnation scent as well: Carthusia Fiori di Capri. It can make walking in the park where dog owners routinely walk their dogs a completely novel experience in perception!

Nevertheless, the picking up of a poopy smell can't be a compass into actual composition after all: The natural oil requires the processing of tons of flowers raising the cost to 10,000$ per kilo of essence, while it would be perfectly easy to add seperate indole to synthetic substitutes in order to produce a compound that would be closed in value to 10$ per kilo. The difference in pricing is staggering, which explains why natural jasmine oil is today only used in minute amounts in specific extrait de parfum formulae and only there; the rest is mythos and marketing communication of the brands.

But not all jasmine fragrances need to be indolic either. Try the non-indolic Armani Sensi and Sensi White Notes. Also get a feel for Jasmine White Moss by E.Lauder or Voile de Jasmine by Bulgari. Nothing "dirty" about them whatsoever!
To construct a light, virginal jasmine without indole, the perfumer has several synthetic options (assuming they're not involved in the masochistic effort of taking the natural and getting it fractioned in order to remove the indole). Hedione in copious amounts is the first choice, as it reproduces a greener, dewier version in contrast to the natural jasmine absolute. It's combination (in elevated ratio within the "jasmine base" thus created) with benzyl acetate, benzyl salicylate (for diffusion and tenacity), alpha amyl cinnamaldehyde and linalool produces the desired effect. These jasmine fragrances are easy to wear, lighter in feel, less heady and do not pose the problem of reminding people of impolite (even if necessary) human functions.
The choice between heaven and hell, as they say, is yours!

 If you haven't caught on the Perfumery Definitions series till now, please visit:


Related reading on Perfume Shrine: The Jasmine Series, Raw Aroma Materials of Perfumery

photos by Horst P.Horst in collaboration with Dali and Lisa with Harp.

22 comments:

  1. A very interesting "materials" post! Since we're having elections today here in the U. S., I'll vote with the indolic versions of jasmine and neroli. My skin has a tendency to eat indoles and skank, so florals with them just end up smelling fuller and less sweet.

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  2. I have trouble with indolic jasmine. There, I said it. Joy smells like dirty panties on me - not poopy, but like sweaty, um, ladyparts, if you get what I mean. (I'm not sure it's the civet; I love Ubar and Climat and Bal a Versailles and Parfum Sacre, and I notice the civet in those but it never bothers me. Rather, it reminds me somewhat of the lovely dusty smell of cat fur.) Sarrasins was a skankfest galore.

    Other white flowers that are frequently described as "indolic" by some perfume lovers don't seem to bother me: tuberose, ylang, orange blossom. Well, I'm not a *big* fan of OB, but that's primarily because it can seem a little soapy and flat to me, not because of some undercurrent of body smell.

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  3. Mimi Gardenia formerly Mystic Knot06:24

    I *think* I adore indoles ... I have tried over and over to love Jasmine White Moss by Estee Lauder but I can't. Joy and I are best friends !
    I do love Jasmal by Creed and A La Nuit .

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  4. D,

    I wish you all the best with the voting results.
    It's very interesting what you say and it has often made me wonder too because I don't perceive "dirty" smells (in perfume) as several others. Is it a matter of skin or perception? That is the question.
    There is thankfully a cornucopia of scents with indolic smell on the market, so you're set. :-)

    (btw, do try Manoumalia if you can)

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  5. M,

    how fascinating, love the breakdown you did on specific flowers!

    Well, I think jasmine is the most blatantly indolic per se. Tuberose is "dirty" but also has other elements in it (rubberiness or a certain "meaty" quality sometimes) which might defray from the intimate aura that jasmine has. Ylang Ylang is sweeter to my nose, but also creamier.
    Orange blossom is usually rendered through a very synthetic way in modern perfumery which indeed would produce the "lathery" vibe you are talking of (and so often it's neroli diluted that produces it rather than actual orange blossom absolute).
    So that leaves us with jasmine, and yes, I can totally see where you're coming from. It's also very difficult to reproduce in scent in all its glory because the vine has several elements to it. Hence the recompositions through synths.
    Joy has a ladyparts bit in the extrait, very true! I'm not its greatest fan overall, so this is personal taste entering the equation although I cannot deny the vintage extrait is a wonder of balance.

    Maybe try Jasmine Emperatrice Eugenie by Creed? This is a full jasmine but with a civet-ambery vibe at the back which makes it creamier and "friendlier". Since you don't have problems with civet...

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  6. Mimi Gardenia (cute name!!),

    thanks for chiming in!
    I personally think Jasmine White Moss is not really about the jasmine. It's like a modernised Cristalle or Diorella (more chyprish than floral) So I definitely see where you're coming from.
    Ohh, A la Nuit is gorgeous if one loves indolic jasmine. And Jasmal is very pretty as well.

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  7. Very interesting post! I love love love Jasmin Full, the only Montale I own, precisely for those days when I want something really dirty. (And I agree -- tuberose's rubber and gardenia's ... whatever seem to divert the attention from the dirty bits.)

    I tend to bring out the naughty in neroli/orange blossom, I assume it's some chemical component they've added.

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  8. Fascinating article! This makes me want to scoop up some jasmine scents (pun intended) and see what all of this indole chatter is about. Although I may already have some...I have a bottle of Bal a Versailles, which I adore, as well as a tiny bit of Joy in extrait left. I also love that! It makes me wonder, too, what's in Amouage's Gold for men, since when smelling that, my mind went right to Joy in extrait. Jasmine is getting sadly overlooked in my collection. That pushy tuberose is taking up so much space!

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  9. Great article; I'm still learning so need to go smell some of the perfumes you mention. I am very familiar with Chypre scents but not so much indoles. I have some vintage Joy to start with. Does vintage Shocking by Schiaparelli have indoles in it? I definitely get a "ladies panties" scent after wearing it a long while.

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  10. Alexandra12:08

    I love idolic jasmine, the only kind of jasmin in perfumes that I like. For instance one like in Organza I can`t stand. The Different Company - Jasmin de Nuit is great, especially for the first half an hour. I also think I can smell it in old formula Ysatis. I have to try Montale. Is it similar to TDC Jasmin, just jasmin not whole fragrance?

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  11. Here I am, late to the party... I found a vintage perfume simply called "Jasmine" by Floris. Yes, it is extrait--I didn't know they made anything in concentrations other than eau de toilette. It is still sealed and I am a little hesitant to open it but if someone dares me, I will...

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  12. March,

    hi there!

    Thanks honey! Jasmin Full is one of the few Montales I deem favorites and that's saying a lot (I think you agree).

    Me thinks the gardenia has elements of mouldy cheese and tuberose is definitely rubbery. These elements can be more pronounced than the sweet, sweet decay, which is probably what's throwing us off in regards to "dirty" as in poopy/rotten decaying matter.

    In regards to neroli and orange blossom on you, my own assesment on what you describe is that it has to do with the ingredients used to render the note, not necessarily of synth nature or not:
    Usually neroli isn't very indolic but they do pair it an awful lot with musk (they go hand in hand and it all goes back to cologne) and the result can be quite intimate sometimes. Orange blossom when used as the natural absolute can be quite naughty and lush, only it's not usually used in significant amounts due to cost. But there are definitely soapy orange blossom frags and naughty orange blossom frags. The latter are often flanked by jasmine and tuberose on either side, finely cornering the market in all -considered- "feminine" smells (sweet decay, ladybits and blood). That's my theory at least. Does it sound logical?

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  13. Jared,

    thanks, looks like I have sent you on a hunt which is excellent. Not that you don't already have a seemingly fine collection!
    I love, love, love the Bal a Versailles. It's even dirtier in the old Eau de Cologne version which I simply adore.
    Do try to scoop up some jasmine (cute pun, so borrowing it!). It's really great.

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  14. Stelma,

    how kind of you to say so!
    Chypres manage to exude a different vibe, musty yes, but in a different way. More dry and powdery, while indole is somehow...wetter, although nothing at all like aqueous/dewy or marine scents. It's hard to explain. It's not a powdery smell and chypres so often have the effect of mossy face powder (not talc).

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  15. Stelma,

    forgot to mention that Schocking does have a ladyparts aura about it, due to multiple things. I think it also has a sweaty effect which contributes to the overall concept.

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  16. A,

    very interesting comment!

    Organza always seemed to me like a synthetic gardenia with sweet bits of vanilla on steroids. It's just taking up the stage. Yet it has some charm if you can stomach such a presence, bigger than life. I can see how it can't be a jasmine lover's dream though. Ysatis certainly played up the jasmine more than Organza, although it's rather more mossy and less vanilla for sure.
    Now TDC Jasmin de Nuit, to me has always been a non-traditional jasmine: It's full of spice! I love the spice (obviously the Ellena family do too) but the jasmine isn't very prominent to really peg it as a jasmine frag. It's utterly lovely though, you have great taste!

    Do try A la Nuit if you can, it's totally close to a real night-blooming jasmine vine, with its heady fruity top at the warmer hours seguing into heady, narcotic sweetness in the later stages.

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  17. QC,

    I admit I haven't tried that one. It's interesting that it's extrait, in older days that was possible. Now they carry Night Scented Jasmine, which hasn't really wowed me personally.
    Is the old really good?

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  18. Brian Shea05:33

    I must be anosmic to indole, because no jasmine absolute I have ever smelled has been in any way 'funky' to me, rich, sensuous, full,yes, but funky, no. And certainly not poopy. I do detect something funky in orange blossom absolute though, a sort of musty, decaying vegetation kind of smell. To me that note is even more pronounced in the orange blossom water absolute. I've never gotten anything 'rubbery' with tuberose either, although myrrh oil to my nose smells a bit rubbery, and saffron has a bit of that as well. I've also read of rose absolutes as having funky off-notes as well, but once again, I've never experienced it!

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  19. Brian,

    thanks for commenting!

    It's more moth-ballish funky than funky in a unwashed body parts funky sense ;D
    I too find jasmine absolute rich, sensuous and full and very pleasurable, even in isolation.
    Tuberose has even more of that mothball funkiness to me, but that's not a deterent. To me it's combination of camphor, sweet floral and some rubber Band-Aid accord that makes up tuberose absolute and I'm referring to Indian tuberose of great quality.
    Rose doesn't really translate as funky no matter what I do! Artichoke yes; funky no... :/

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  20. I've never understood the "indolic=poopy" trope so bandied about by perfumistas. I, too, get hints of mothballs and decay from heavy indoles rather than anything fecal, and then only as a facet of the scent, not the whole story. (If Joy really smelled like a soiled diaper, people wouldn't wear it, yes?)

    Indole is crucial to good jasmine scents to make them lush, vivid, and true-to-life, and to keep them from smelling like bubble tea. When I deign to wear jasmine perfumes, I insist on the indolic kind. Bring on the mothballs!

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  21. Darryl,

    I think "fecal" and poopy" are all in the mind of people with an aversion to natural smells in the first place.
    To illustrate: Bal a Versailles is supposed to be "dirty" in a "fecal" and "naughty" way (so much civet in some concentrations of it). But would you flat out say "something smells like poop here" while smelling it? Nope. It's just a hypersensitivity on the part of us not wanting to offend.

    Perhaps the same to some degree is happening with indolic fragrances: people are wary of appearing like they dragged something off the attic and wore it without washing to clear the smell, "like old ladies do" (another dread!). It's all paying too much attention IMO to something that just isn't such an important aspect of the finished product. In the end, it's always perceived as perfume, not mothballs. (Unless someone is seriously lacking in experience or is a child, to whom everything is new, naturally and we don't expect children to come up with sophisticated terms but with familiar associations).

    Though I need to point out I absolutely agree with you that jasmine without indoles isn't jasmine. ;-) :-)

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  22. I feel the same as Mals86. I'm glad I'm not the only one. I had always thought that jasmine smelled like urine to me, but perhaps a pair of dirty panties is more accurate.

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