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  1. #1

    Default Iso Eugenol replacer

    Hey all, I know this has been discussed briefly on here before but I didn't find my answer in what I read there.

    Basically I need a replacer for Iso Eugenol that comes as close as possible to the real thing. While happily I can ignore IFRA in this country, I can't ignore the cosmetics standards and they restrict the use of iso eugenol to 0.02 of a fragrance.

    The maximum amount of iso eugenol I use in an accord is 10% so working on the premise of a 10% base diluted to 20% as a parfum, I can use around 1%. My thought was that it would be best to create a replacer base that has 1% iso eugenol and the rest to fill the gaps.

    Here's my main problem: I find methyl diantilis too powdery to really be a viable replacer (not to mention the fact that I find it very distasteful that Givaudan sells it at twice the price of iso eugenol since their friends at IFRA conveniently lobbied to ban the real thing).

    I have looked at dihydroeugenol and I think it's odor is quite a good match - though it lacks the staying power. Methyl Diantilis and Iso Eugenol are both around 400 hours, while dihydro eugenol is only 92. Methyl iso eugenol is 240 but the odor doesn't seem quite right to me.

    Any other suggestions?

    If the longevity of dihydroeugenol was the same as iso eugenol I would use it combined with a little vanillin to soften it like iso eugenol but alas that doesn't seem possible.

    I have made an accord with around 80% dihydro eugenol, 10% methyl diantilis, and the rest a mix of DPG and iso eugenol and the scent profile is fairly good but - as I said - longevity is going to be an issue.

  2. #2

    Default Re: Iso Eugenol replacer

    Jamie, are you going by the substantivities listed on Goodscents or by your own findings? The substantivities listed on Goodscents aren't always entirely accurate, although they might be in this instance.
    Last edited by Pears; 18th October 2015 at 02:20 AM.

  3. #3

    Default Re: Iso Eugenol replacer

    Quote Originally Posted by Pears View Post
    Jamie, are you going by the substantivities listed on Goodscents or by your own findings? The substantivities listed on Goodscents aren't always entirely accurate, although they might be in this instance.
    I use them as a rough guide and then go from my experience; in my experience with dihydro eugenol it doesn't last anywhere near as long.

  4. #4

    Default Re: Iso Eugenol replacer

    Isoeugenyl phenylacetate sounds interesting, though not as close to isoeugenol as you're asking. Edward Maurer (1958) writes: "Has a mild, but very sweet spicy clove-pink aroma with a honey-vanilla undertone. . . . This may be regarded, perhaps, as the fixative par excellence for all fine blossom compositions. At 1% it imparts a noticeable freshness and uplift to Carnation compounds, and also a piquancy to Lilac, Jasmin and Light Floral bouquets." I haven't tried it (I'd like to).

  5. #5

    Default Re: Iso Eugenol replacer

    Quote Originally Posted by jfrater View Post
    I use them as a rough guide and then go from my experience; in my experience with dihydro eugenol it doesn't last anywhere near as long.
    I think that I'd probably keep the dihydroeugenol as the primary component, as well as the methyl diantilis, and then add a little eugenyl acetate or isoeugenyl acetate for increased longevity. I might also add a little ethyl guaiacol, which is structurally almost identical to eugenol/isoeugenol - possessing one less carbon atom. However, although it's odour is clove-like, it also possesses a smoky note and therefore needs to be used a little more carefully. That's just my 2 cents. Good luck.

    Pears
    Last edited by Pears; 18th October 2015 at 06:05 AM.

  6. #6

    Default Re: Iso Eugenol replacer

    Quote Originally Posted by Pears View Post
    I think that I'd probably keep the dihydroeugenol as the primary component, as well as the methyl diantilis, and then add a little eugenyl acetate or isoeugenyl acetate for increased longevity. I might also add a little ethyl guaiacol, which is structurally almost identical to eugenol/isoeugenol - possessing one less carbon atom. However, although it's odour is clove-like, it also possesses a smoky note and therefore needs to be used a little more carefully. That's just my 2 cents. Good luck.

    Pears
    Thanks for that. I have looked into acetyl isoeugenol and ordered some to try out. Apparently I can use it and it is technically fine to do so - but once it in in the perfume composition it decomposes to iso eugenol It is a trick that can be used to get around the restrictions. On the other hand I have also read that it is not really a suitable one for one replacement so I'll have to do some experimenting.

    I don't have ethyl guiacol - I'll order some to try it out. Robertet does a nice guiac heart which has had much of the smokiness removed - I wonder if there is a similar version of ethyl guiacol around.

  7. #7

    Default Re: Iso Eugenol replacer

    Quote Originally Posted by Alysoun View Post
    Isoeugenyl phenylacetate sounds interesting, though not as close to isoeugenol as you're asking. Edward Maurer (1958) writes: "Has a mild, but very sweet spicy clove-pink aroma with a honey-vanilla undertone. . . . This may be regarded, perhaps, as the fixative par excellence for all fine blossom compositions. At 1% it imparts a noticeable freshness and uplift to Carnation compounds, and also a piquancy to Lilac, Jasmin and Light Floral bouquets." I haven't tried it (I'd like to).
    Interesting - that sounds like a description of methyl diantilis curiously. I will order some - it sounds like it could be beneficial to some other bases I am working on right now too.

  8. #8

    Default Re: Iso Eugenol replacer

    Quote Originally Posted by jfrater View Post
    (not to mention the fact that I find it very distasteful that Givaudan sells it at twice the price of iso eugenol since their friends at IFRA conveniently lobbied to ban the real thing).
    would it be more tasteful if they gave it away for free instead of ripping you off in this most brutal way ?
    have you at least considered the possibility that the production cost is higher ?
    or do you think they just snip with their fingers and Isoeugenol (which is not the starting material btw) magically turns into Methyl Diantilis ?

  9. #9

    Default Re: Iso Eugenol replacer

    Quote Originally Posted by 'Timon View Post
    would it be more tasteful if they gave it away for free instead of ripping you off in this most brutal way ?
    have you at least considered the possibility that the production cost is higher ?
    or do you think they just snip with their fingers and Isoeugenol (which is not the starting material btw) magically turns into Methyl Diantilis ?
    Of course not; but on the other hand, you completely missed my point. I have absolutely no problem with companies charging what they want for their products - even if it's a $600 bottle of diluted galaxolide courtesy of Amouage—I even own some! My problem is when companies like Givaudan fund an organization that lobbies on their behalf to ban the (much cheaper) competition. THAT was the point I was making.
    Last edited by jfrater; 18th October 2015 at 09:49 AM.

  10. #10

    Default Re: Iso Eugenol replacer

    I don't think I missed your point completely like you suggest. It's rather the way that I don't share your opinion in this case.

    You complained explicitly about the pricing as if in some way this is part of a distasteful business strategy at the cost of the perfumers choice of materials: Ban a product so a replacement can be sold at higher price. My point is that the price of the material is not a good argument, since it depends in first place on the production cost. You might argue that overall the profit is still higher (probably it is somewhat!), but I honestly don't think this is their intention in supporting IFRA.
    Well I could go on and share my thoughts on IFRA, if you wish to.
    Talking about perfumery is another option and more interesting of course. In any case please don't take my objections personal. I have the feeling anything IFRA related often stirs up emotions, myself included.

  11. #11

    Default Re: Iso Eugenol replacer

    Quote Originally Posted by jfrater View Post
    even if it's a $600 bottle of diluted galaxolide courtesy of Amouage.
    ROFL!! We have got to love Jubilation XXV men. You forgot to mention the diluted iso e super though...

  12. #12

    Default Re: Iso Eugenol replacer

    Quote Originally Posted by Pears View Post
    I think that I'd probably keep the dihydroeugenol as the primary component, as well as the methyl diantilis, and then add a little eugenyl acetate or isoeugenyl acetate for increased longevity. I might also add a little ethyl guaiacol, which is structurally almost identical to eugenol/isoeugenol - possessing one less carbon atom. However, although it's odour is clove-like, it also possesses a smoky note and therefore needs to be used a little more carefully. That's just my 2 cents. Good luck.

    Pears
    Just curious, to what extent would you say we can move away from Methyl Diantillis' powderiness by exploring this direction? (I actually really like m.diantillis on its own merits, but I have to agree that it's pronounced powdery facets make it nothing like an isoeugenol replacer.)

  13. #13

    Default Re: Iso Eugenol replacer

    related to the topic of this thread:
    I always thought Dianthine is a carnation base by Firmenich. However, I noticed the mention of "Dianthine" in the book Scent & Chemistry 2011, it's apparently the name for Guaiacol Allyl ether! (1-Allyloxy-2-Methoxybenzene)
    The TGSC site hardly reveals anything:
    http://www.thegoodscentscompany.com/data/rw1423371.html

    now there is another compound, the closely related 1-Allyloxy-2-Ethoxybenzene or Guaethol Allyl ether
    at least with odor description:
    http://www.thegoodscentscompany.com/data/rw1020791.html

    perhaps the first compound was also part of the original Dianthine base ? Another mystery to solve...

  14. #14

    Default Re: Iso Eugenol replacer

    Quote Originally Posted by Iforgot View Post
    ROFL!! We have got to love Jubilation XXV men. You forgot to mention the diluted iso e super though...
    Sorry - I just figured the iso-e-super was too obvious to mention

  15. #15

    Default Re: Iso Eugenol replacer

    Quote Originally Posted by 'Timon View Post
    related to the topic of this thread:
    I always thought Dianthine is a carnation base by Firmenich. However, I noticed the mention of "Dianthine" in the book Scent & Chemistry 2011, it's apparently the name for Guaiacol Allyl ether! (1-Allyloxy-2-Methoxybenzene)
    The TGSC site hardly reveals anything:
    http://www.thegoodscentscompany.com/data/rw1423371.html

    now there is another compound, the closely related 1-Allyloxy-2-Ethoxybenzene or Guaethol Allyl ether
    at least with odor description:
    http://www.thegoodscentscompany.com/data/rw1020791.html

    perhaps the first compound was also part of the original Dianthine base ? Another mystery to solve...
    The original dianthine base (now seriously wrecked by Firmenich thanks to them following IFRA guidelines rather than European regulations) was extremely basic - being largely eugenol, ylang ylang, cinnamic alcohol, heliotropin and a few others. No unusual or complex synthetics were used. It was one of those vintage bases created to make a single chemical more usable (as Mousse de Saxe was to IBQ).

    The chemical in question in Dianthine was Eugenol (at more than 50% of the original formula). As far as I am aware there was no iso eugenol in the original. If you are concerned about IFRA restrictions you can't use the original - or recreate it for that matter. On the other hand, there is absolutely nothing in the original that would prevent you using it in massive amounts today if you are ignoring IFRA and following only the European cosmetics guidelines which don't restrict eugenol but merely require it to be on the label. Ditto with the cinnamic alcohol (around 20% of the original).

    I have a sample of the new dianthine from Firmenich and while it is initially very similar to the odour profile of the original, it fades within a couple of minutes on the skin. My replica of the original dianthine lasts for hours on the skin as you would expect with such a high dose of cinnamic alcohol and orris resin.

    This is actually a really good example of how good fragrances can be ruined by following IFRA rules. L'Origan used 20% dianthine in the original formula. That is now, of course, about 15% too much. The original had to balance out an enormous dose of methyl ionone. Needless to say, the new dianthine can't compete with the necessary methyl ionones so the fragrance is discontinued. On the other hand Guerlain - who copied L'Origan in L'Heure Bleue - just accepted that their new version of that perfume would last 10 seconds on the skin instead of 10 hours. That is, of course, exacerbated by their corporate rule against the use of animal products - so goodbye castoreum and civet too.

  16. #16
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    Default Re: Iso Eugenol replacer

    With your membership, you can see the GC I had done on Vintage Firmenich Dianthine base on Perfumertalk.

    It is 41% eugenol, and 20% Cinnamic Alcohol.
    No Isoeugenol nor any other eugenyl acetates.

    I *would* indeed caution about higher dosages of Eugenol, as it can indeed become an allergenic issue.
    My Red Leather was composed and it had 6% eugenol, and after wearing it consecutively for many days, whenever I put it on, it would make me itch after a few hours, right where I sprayed it on. So I reduced the eugenol content by roughly 3/4 of that 6 grams, and now it wears fine.

    I've done quite a bit of research on replacements for the eugenolic type content, and the more esoteric eugenol elements are very hard to come by, unless you book a Chinese chemical co to make them for you. Even the main Clove/eugenol producers in indonesia said the same thing.

    It's a difficult thing, that I don't have a good solution for yet.

    Certainly Dihydroeugenol is a good start.

    With my selection of materials available, the best in my mind are these, in order of preference:
    Eugenol
    Isoeugenol
    Dihydro Eugenol
    Isoeugenyl Acetate
    Eugenyl Acetate

    Several others are more vanillic or powdery, Methyl Eugenol is so underwhelming, It is indeed difficult to replace both Eugenol and Isoeugenol.

    PK
    Paul Kiler
    PK Perfumes
    http://www.PKPERFUMES.com
    In addition to Our own PK line, we make Custom Bespoke Perfumes, perfumes for Entrepreneurs needing scents for perfumes or products, Custom Wedding Perfumes, and even Special Event Perfumes.

  17. #17

    Default Re: Iso Eugenol replacer

    Quote Originally Posted by pkiler View Post
    With your membership, you can see the GC I had done on Vintage Firmenich Dianthine base on Perfumertalk.

    It is 41% eugenol, and 20% Cinnamic Alcohol.
    No Isoeugenol nor any other eugenyl acetates.

    I *would* indeed caution about higher dosages of Eugenol, as it can indeed become an allergenic issue.
    My Red Leather was composed and it had 6% eugenol, and after wearing it consecutively for many days, whenever I put it on, it would make me itch after a few hours, right where I sprayed it on. So I reduced the eugenol content by roughly 3/4 of that 6 grams, and now it wears fine.

    I've done quite a bit of research on replacements for the eugenolic type content, and the more esoteric eugenol elements are very hard to come by, unless you book a Chinese chemical co to make them for you. Even the main Clove/eugenol producers in indonesia said the same thing.

    It's a difficult thing, that I don't have a good solution for yet.

    Certainly Dihydroeugenol is a good start.

    With my selection of materials available, the best in my mind are these, in order of preference:
    Eugenol
    Isoeugenol
    Dihydro Eugenol
    Isoeugenyl Acetate
    Eugenyl Acetate

    Several others are more vanillic or powdery, Methyl Eugenol is so underwhelming, It is indeed difficult to replace both Eugenol and Isoeugenol.

    PK
    I have seen your GCMS - it was quite insightful but interestingly Arcadi Boix Camps (who has seen the original formula) said it had significantly more eugenol than the GCMS would indicate. Certainly when I make it up at more than 50% it does seem to smell similar to the current dianthine base. I wonder if DEP may be the cause of the discrepancy.

    Have you had experience with isoeugenol acetate? I am hoping that one will be the answer given that it converts to isoeugenol in the presence of alcohol.

  18. #18
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    Default Re: Iso Eugenol replacer

    There is this one that I'd love to get my nose and grubby little hands on:

    Acetaldehyde ethyl isoeugenyl acetal

    http://www.thegoodscentscompany.com/data/rw1020471.html

    There is a Dianthine formula on p. 3 of this patent with Eugenol @ 50%
    https://patentimages.storage.googlea.../US4383943.pdf

    But finding a supplier for the above material is difficult...


    Jamie, I did mention the Isoeugenyl acetate in my list, @ #4 in preference . . . But it is weaker than the others, the list is a vertical sort, in terms of strength and odor profile for the genre, without going to vanilla or powder.

    PK
    Paul Kiler
    PK Perfumes
    http://www.PKPERFUMES.com
    In addition to Our own PK line, we make Custom Bespoke Perfumes, perfumes for Entrepreneurs needing scents for perfumes or products, Custom Wedding Perfumes, and even Special Event Perfumes.

  19. #19

    Default Re: Iso Eugenol replacer

    Quote Originally Posted by pkiler View Post
    There is this one that I'd love to get my nose and grubby little hands on:

    Acetaldehyde ethyl isoeugenyl acetal

    http://www.thegoodscentscompany.com/data/rw1020471.html

    There is a Dianthine formula on p. 3 of this patent with Eugenol @ 50%
    https://patentimages.storage.googlea.../US4383943.pdf

    But finding a supplier for the above material is difficult...


    Jamie, I did mention the Isoeugenyl acetate in my list, @ #4 in preference . . . But it is weaker than the others, the list is a vertical sort, in terms of strength and odor profile for the genre, without going to vanilla or powder.

    PK
    What a great couple of formulae for dianthine bases! I love the first one using cinnamon oil instead of cinnamic alcohol - I adore cinnamon oil. As for 1-(1-ethoxyethoxy)-2-methoxy-4-[(E)-prop-1-enyl]benzene - looks like a trip to a Chinese manufacturer may be needed.

    I will continue to try to make a replacer with the maximum iso-eugenol allowed. My bottle of natural iso eugenol just arrived and I really do want to use it.

  20. #20

    Default Re: Iso Eugenol replacer

    Jamie, I'm curious to know why you wish to use isoeugenol when according to Paul, the GC/MS didn't reveal any in the Dianthine base that you wish to replicate.
    Last edited by Pears; 19th October 2015 at 07:21 AM.

  21. #21

    Default Re: Iso Eugenol replacer

    Quote Originally Posted by pkiler View Post
    There is this one that I'd love to get my nose and grubby little hands on:
    PK
    this is one of the very few patents which showed up yesterday evening (night...) when I was trying to get any useful information on the mysterious compound named Dianthine mentioned in the S&C book (most valuable). Still no success in this regard.
    But this acetal is certainly very interesting, the authors even prefer it over the mixture containing isoeugenol.
    Of course from an IFRA point of view this is still unsafe, since it can be expected to form Isoeugenol (more so than Isoeugenyl acetate). But I don't care, it sounds lovely and it's very simple to prepare as well.

    An alternative to Methyl Isoeugenol, but hard to get as well: Ethyl Isoeugenol.

  22. #22

    Default Re: Iso Eugenol replacer

    Quote Originally Posted by Pears View Post
    Jamie, I'm curious to know why you wish to use isoeugenol when according to Paul, the GC/MS didn't reveal any in the Dianthine base that you wish to replicate.
    I already have my vintage dianthine base and it's completely compliant with NZ cosmetics requirements (though totally not IFRA compliant). I want to use Iso Eugenol in other bases and perfumes to support eugenol in the heart without being too powdery.




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