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  1. #1

    Question Gamma Methyl Ionone

    Does "gamma methyl Ionone" refer to a single chemical or a class of chemicals? I had a sample analyzed by GCMS and one of the constituents was Gamma Methyl Ionone, but the CAS number was really strange: 101325-32-0. PA sells two chemicals with the name gamma methyl ionone, both with still different cas numbers!

    Could someone clear up my confusion?

  2. #2

    Default Re: Gamma Methyl Ionone

    Methyl Ionone refers to a class of chemicals. Many ingredient suppliers produce Methyl Ionone mixtures, of differing amounts. Gamma Methyl Ionone is one such mixture, which happens to contain a lot of the single chemical Gamma Methyl Ionone, but it also contains other Methyl Ionones ( called alpha, beta etc.) . They are the various isomers of Methyl Ionone. It is quite possible that two different suppliers of Methyl Ionone will sell a mix called Gamma Methyl Ionone, and the two will be different; although, usually, they will both be high in the Gamma isomer.

  3. #3

    Default Re: Gamma Methyl Ionone

    BTW: Methyl ionone gamma from PA is purified Methyl ionone alpha iso alias Isoraldeine. I doubt you will find real gamma isomer somewhere.

  4. #4

    Default Re: Gamma Methyl Ionone

    BTW I bet you that the gamma Methyl Ionone from PA contains some alpha and beta Methyl Ionone too. I do not know of anyone providing individual isomers of Methyl Ionone.

  5. #5

    Default Re: Gamma Methyl Ionone

    Yes of course David. Purified does not mean pure Main component of Methyl ionone gamma is Methyl ionone alpha iso . I doubt there is gamma isomer, maybe in trace amounts...

  6. #6

    Default Re: Gamma Methyl Ionone

    There is a gamma Methyl Ionone isomer. Givaudan and IFF ( and others) sell mixtures of Methyl Ionone where it is the major component.

  7. #7
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    Default Re: Gamma Methyl Ionone

    I have methyl ionone gamma 70, 90 & isoraldeine, they all smell different but similar. The 90 is a bit more violet and "heavy" than isoraldeine and the 70 is slightly more woody and orris-like than the other two.
    Justin E. Beasley

  8. #8

    Default Re: Gamma Methyl Ionone

    Quote Originally Posted by David Ruskin View Post
    There is a gamma Methyl Ionone isomer. Givaudan and IFF ( and others) sell mixtures of Methyl Ionone where it is the major component.
    Are you really sure David ?

    IFF:
    METHYL IONONE GAMMA A CAS 127-51-5
    3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one (isomers)

    METHYL IONONE GAMMA COEUR CAS 127-51-5
    3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one (isomers)

    METHYL IONONE GAMMA PURE CAS 127-51-5
    3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one (isomers)


    In all cases is major component CAS 127-51-5 - alpha-iso-Methylionone.
    If you look inside MSDS http://www.johndwalsh.com/MSDS/IFF/m...mma%20pure.pdf or http://johndwalsh.com/MSDS/DSM2011/M...070%20MSDS.pdf ( not IFF,but for demonstration only ) there is no gamma isomer.

    for example Methyl ionone gamma 70 from previous MSDS contain:

    60-70% methyl ionone alpha iso
    17-30% methyl ionone alpha
    3 -14% methyl ionone beta iso
    0 -10% methyl ionone beta
    Last edited by Milhaus; 18th April 2014 at 06:43 AM.

  9. #9

    Default Re: Gamma Methyl Ionone

    I really can't be bothered to keep on arguing with you when I know what I am talking about. Having seen countless GC/MS traces where several isomers of Methyl Ionone were identified, and where the gamma isomer was often the largest component of the Methyl Ionone mix; I state unequivocally that Methyl Ionone containing a large proportion of the gamma isomer is widely used, and widely available.

    Cas No. 127-51-5 is alpha Methyl IOnone
    Cas No. 79-89-0 is beta Methyl Ionone
    Cas No. 1335-46-2 is N Methyl Ionone
    and
    Cas, No. 1322-70-9 is gamma Methyl Ionone.

    Got it?

  10. #10

    Default Re: Gamma Methyl Ionone

    I didn't think that you were disagreeing with eachother, except on the last point. I'd have to agree with David regarding that point. If you look at the specs for Givaudan's Isoraldiene cetone alpha, it lists CAS no. 1335-46-2 and 127-51-5. If gamma Methyl ionone (127-51-5) was considered a mixture of isomers, they probably wouldn't also have listed N methyl ionone (1335-46-2).

    http://www.givaudan.com/webcom/v/ind...005b53410aRCRD

    Gamma Methyl ionone is usually accompanied by other isomers but CAS no 127-51-5 relates to only the gamma Methyl ionone isomer, which is the main component.

    Quote Originally Posted by Milhaus View Post
    Main component of Methyl ionone gamma is Methyl ionone alpha iso . I doubt there is gamma isomer, maybe in trace amounts...

    Gamma Methyl ionone is a synonym of alpha Isomethyl ionone, they are one and the same.

    http://ec.europa.eu/consumers/cosmet...tails&id=39665
    http://www.takasago.com/cgi-bin/detail.cgi?key=C013182
    Last edited by Pears; 18th April 2014 at 02:04 PM.

  11. #11

    Default Re: Gamma Methyl Ionone

    No they are not the same:

    1-Penten-3-one, 1-(2,6,6-trimethyl-2-cyclohexen-1-yl) (alpha-methylionone isomer)
    1-Penten-3-one, 1-(2,6,6-trimethyl-1-cyclohexen-1-yl) (beta-methylionone isomer)
    1-Penten-3-one, 1-(6,6-methyl-2-methylenecyclohex-1-yl) (gamma-methylionone isomer)

    CAS No. 1335-46-2 is mixture of methyl ionone isomers

    Here is example of typical "methyl ionone" mixture:
    alpha-iso-Methylionone (55-65%)
    beta-iso-Methylionone (4-7%)
    alpha-n-Methylionone (22-32%)
    beta-n-Methylionone (1-5%)
    gamma-n-Methylionone (1-5%)


    "Methyl ionone gamma" is only bad TRADE name for mixture of methyl ionone isomers where is major component alpha-iso-Methylionone . But maybe i am stupid and dont understand it...

  12. #12

    Default Re: Gamma Methyl Ionone

    I agree that it's a bad name to use because there's actually a genuine gamma n-Methyl ionone and gamma iso-Methyl ionone, which are different to alpha Isomethyl ionone. However, one of the synonyms for alpha Isomethyl ionone is gamma Methyl ionone. Atleast according to some sources:

    "Gamma (iso-alpha) methyl ionone"

    http://www.privi.com/product-details.asp?cno=C10910011
    http://ff.florachem.com/products/m-r

    "Gamma Isomer Min. 65%"

    http://www.morayaglobal.com/gammamethylionone.asp

    The information from one source conflicts with this, so it's up to you which you believe.


    http://books.google.co.uk/books?id=h...20pure&f=false
    Last edited by Pears; 18th April 2014 at 02:06 PM.

  13. #13

    Default Re: Gamma Methyl Ionone

    Dont belive sellers I have requested MSDS from the India seller you have mentioned , i bet they dont know difference between these isomers.
    Your latest url say everything.
    Short citation from this book "Fragrance Chemistry: Science of the Sense of Smell":
    "In commerce methyl ionone mixture rich in alpha iso methyl ionone are sold under the name "gamma" methyl ionone"

    Maybe David could tell us where to buy methyl ionone mixture containing big amount of gamma methyl ionone.

  14. #14
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    Default Re: Gamma Methyl Ionone

    Confusing sometimes...
    Paul Kiler
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  15. #15

    Default Re: Gamma Methyl Ionone

    Don't believe Indian sellers. Best sources of all Methyl Ionones are IFF and Givaudan.

  16. #16

    Default Re: Gamma Methyl Ionone

    Here are the leffingwell pictures of the gamma isomers:

    http://www.leffingwell.com/chirality...thylionone.htm

    Then I found this:

    "United States Patent 3,840,601 PROCESS FOR PREPARATION OF METHYL IONONES Peter S. Gradeff, Andover, N.J., assignor to Rhodia Inc., New York, N.Y. No Drawing. Filed Feb. 7, 1972, Ser. No. 224,258 Int. Cl. C07c 49/18, 29/00 US. Cl. 260-594 11 Claims ABSTRACT OF THE DISCLOSURE A process is provided for the preparation of methyl ionones by the aldol condensation of citral and methyl ethyl ketone at a temperature below about 10 C., followed by dehydration to form a pseudo methyl ionone,

    15 which can then be cyclized to form the methyl ionone.

    Methyl ionone is a term used in perfumery to designate ionones which are prepared by the condensation-dehydration reaction of citral with methyl ethyl ketone, followed by cyclization. A mixture of several methyl ionones is obtained:

    gamma iso gamma normal The alpha-iso isomer has been incorrectly referred to as gamma-methyl ionone, and this name is still used to designate material that is rich in this isomer. The Essential Oil Association Standard for methyl ionone defines gamma-methyl ionone as a mixture of at least 60% iso content. The iso isomers, mainly alpha with some beta and gamma, are the most desirable of all the methyl ionones as perfume ingredients, and thus the preparation of pseudo-iso-methyl ionone has been given prime attention."

    Caveat: I'm no chemist; just an artist trying to be helpful. I have no opinion, and should not. This might be a uselss conversation, and I might be just making it worse...
    Last edited by DrSmellThis; 19th April 2014 at 12:00 AM.

  17. #17

    Default Re: Gamma Methyl Ionone

    You answered the Original question; as did I. The rest is flim-flam.

  18. #18

    Question Re: Gamma Methyl Ionone

    For mine (and anyone else's) future reference, 101325-32-0's systematic name is [1a(E),3a]-4-(2,2,3-trimethyl-6-methylenecyclohexyl)-3-Buten-2-one

  19. #19

    Default Re: Gamma Methyl Ionone

    Ionone alert!

    Today I noticed that methyl ionone gamma pure (IFF) is being sold here: http://www.creatingperfume.com/methy...onaline95.aspx

    While these ionone products are confusing, they're also some of the most interesting materials.

  20. #20

    Default Re: Gamma Methyl Ionone

    On all the confusion and argument: Clear communication only occurs when seeking to interpret words the way the speaker or writer meant them.

    Not by imposing one's concept of what words ought to mean onto to what the person said.

    The information is already presented as to variation in meaning in this case. In particular, David provided the CAS numbers, which are unambiguous.

  21. #21

    Default Re: Gamma Methyl Ionone

    Quote Originally Posted by Bill Roberts View Post
    On all the confusion and argument: Clear communication only occurs when seeking to interpret words the way the speaker or writer meant them.

    Not by imposing one's concept of what words ought to mean onto to what the person said.

    The information is already presented as to variation in meaning in this case. In particular, David provided the CAS numbers, which are unambiguous.
    What I said above was a general statement and had nothing to do with the information set forth in this thread. There are many ionones, and whether or not there is a CAS number provided, they can be a bit confusing and it takes time to become familiar with them. If that were not true, there would be less of a need to discuss them and this thread probably wouldn't be here. That's all I meant. Perhaps I should have been more clear.

  22. #22

    Default Re: Gamma Methyl Ionone

    my reply really was regarding the overall and certainly not your preceding post

  23. #23

    Default Re: Gamma Methyl Ionone

    If only Ionone this before........
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  24. #24

    Default Re: Gamma Methyl Ionone

    Quote Originally Posted by mumsy View Post
    If only Ionone this before........
    Very clever

  25. #25

    Default Re: Gamma Methyl Ionone

    Quote Originally Posted by mumsy View Post
    If only Ionone this before........
    Genius.

    Do you dabble in ionones?

  26. #26

    Default Re: Gamma Methyl Ionone

    Quote Originally Posted by ToddHuyett View Post
    Do you dabble in ionones?
    It might be beta if I did.
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  27. #27
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    Default Re: Gamma Methyl Ionone

    Fascinating reading, all the above, as I try to find more written info on Takasago's Methyl Ionone Gamma EQ (I have no idea what EQ stands for and I guess that's my point here...)

    This issue, I mean aroma discrepancies between products obtained from one seller to the next with the identical chemical name, exists with many other ingredients as well, not just the big family of ionones we all love so much. However, differences among the ionones is perhaps more noticeable –or rampant– because there are mathematically such multitudinous possibilities for isomeric mixtures by specific percent or slight impurities to "bend" the aroma profile toward this direction or that.

    Product obtained from minor manufacturers is just an annoyance because it means that one batch can vary quite a bit from the next, the variances not necessarily being anything calculated, but rather merely a result of production sloppiness, such as differences in the age of the stock by the time it arrives under your nose (which is always only a matter of trust, regardless of what's stamped on the flask), the age –and hence level of degradation and thus impurities– of the precursor chemicals the product was manufactured from, vagaries in distillation temperatures, type and cleanliness of the metal and glass hardware used for this, etc, etc. I'm talking about product from "cheap and dirty" industrial sources such as India and China, etc. OK... I shouldn't single out certain countries, should I? Slap my face. I mean from any manufacturing plant that doesn't have a major reputation for quality control, regardless of where on the globe it's located.

    IMHO, the major houses such as Takasago, Firmenich, Givaudan, IFF, Symrise, etc. also create their own "secret house blends", although not officially identified as such. Their products often have what appears to be identical labeling, yet the aroma profile consistently differs between Brand A and Brand B. Their products are at least usually reliably the same from one batch the the next, one year to the next, and reliably reflect that house's well-cared-for "signature" for the specific product, but differ from one another –again, even though they may be labeled as what technically "should be" the same single ingredient with the same CAS number. I consider these, with a wink, as secret "proprietary blends." The only way a perfumer can learn one from next is by sampling various brands, then faithfully sticking to one brand if s/he wants to consistently obtain the same odor profile. I think it's a way of developing brand loyalty among their buyers.
    I have never read it and I can't prove it, but just like winemakers, I personally suspect that Firmenich, et al. actually add or remove specific traces of this and that isomer or other trace "byproducts" to give their branded aldehydes and other products a unique aroma profile without the buyer ever actually knowing what was done that makes that ingredient perform ever so slightly "better", "differently" or "uniquely" from another brand with the same generic name. In other words, C-11 enic aldehyde doesn't inevitably have the same smell. Think of different brands of, say, beta ionone as different trademarks of single malt whiskey. All may have the same legal and technical designation, yet the human palate can often detect a drastic difference between one house's output and another's. No one can really know what chemical technician has tinkered around ever so slightly with this and that trace material, a purposeful-accidental "slip" in temperature or oxidation level during synthesis, distillation or whatever. Trade secrets abound in perfumery. We can never forget that. I guess we can do nothing other than try to consider it part of the mystery, part of the fun of it all.
    Last edited by mastorer; 20th April 2015 at 06:35 PM.
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  28. #28

    Default Re: Gamma Methyl Ionone

    I'm curious about "Isoraldeine Cetone Alpha" from Givaudan. Has anyone ever tried it and is it worth seeking out over Isoraldeine 95 for example? I found a price list online which says it's a bit more expensive than their other methylionone offerings.

    It's described by Givaudan on TGSC like this:

    Odor: Orris, Woody, Powdery background
    Use: Cetone Alpha is a highly refined alpha-iso-methyl ionone used in rich floral perfumes where an exceptional quality of methyl ionone is required.
    Last edited by Renegade; 6th June 2015 at 12:09 PM.

  29. #29
    New Member jfreddd's Avatar
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    Default Re: Gamma Methyl Ionone

    Quote Originally Posted by ToddHuyett View Post
    Ionone alert!
    While these ionone products are confusing, they're also some of the most interesting materials.
    Yep.
    Last edited by jfreddd; 17th April 2019 at 02:50 AM. Reason: dis-display of confusion
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  30. #30

    Default Re: Gamma Methyl Ionone

    Quote Originally Posted by mumsy View Post
    If only Ionone this before........

    Hahah
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