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  1. #1
    gecko214's Avatar
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    Default dimethyl anthranilate vs methyl anthranilate

    I occasionally play around making up the classics from the Louis Appell formulas. I don't always have everything and so I improvise when necessary (I highly recommend it by the way, you really learn a lot). One of the chemicals I don't have is dimethyl anthranilate (I have methyl anthranilate) . He uses dimethyl-A pretty liberally in many of these formulas, so I am wondering if I should get some. Good Scents supplier drop down section says the following: "Dimethyl Anthranilate is similar in use to Methyl Anthranilate, but it will not form Schiff bases with the aldehydes and has little or no tendency to discolour."

    Since I don't have both materials to compare, would anyone be able to verify that statement? If I don't care too much about discoloration and the eventual formation of schiff bases, should I bother investing in getting dimethyl anthranilate? Is it's odor profile/strength/longevity significantly different? Any other useful info on this material?

  2. #2

    Default Re: dimethyl anthranilate vs methyl anthranilate

    I donít use dimethyl anthranilate a huge amount myself, though I do have some. Alone, the odours of these two are very similar indeed, however while discolouration may not be a concern for you, the formation of Schiffís Bases (or the lack of them) will certainly influence the odour of the blend if it contains any aldehydes - and most blends do - the SB usually smells similar to the parent aldehyde, but much milder and softer.

    What you are likely to find if you substitute methyl anthranilate for dimethyl anthranilate therefore is that initially it will smell pretty-much as intended, but over time the aldehydes will be softened and their impact reduced: you may well think thatís a good thing but it will surely be different from what Appell designed.

    One other important difference is that the dimethyl form is the subject of an IFRA restriction standard, while the methyl is not - thatís because the former is photo-toxic.
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    Chris Bartlett
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  3. #3
    gecko214's Avatar
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    Default Re: dimethyl anthranilate vs methyl anthranilate

    Thanks Chris,

    This is very helpful.

    You are right, I don't mind the aldehydes being softened, because mostly I find them to remind me of everything I don't like in "artificial" scents. This is probably because of bad associations in my past with cheap products containing them and my own inability to dose them properly when I try to use them.... Still, I guess I had probably better get some. It can't be very expensive. And I try to collect anything restricted by IFRA just on principle.

  4. #4

    Default Re: dimethyl anthranilate vs methyl anthranilate

    No problem.

    Donít forget though that it isnít just the aliphatic aldehydes that will react with methyl anthranilate but also all the others, including things like Vanillin, Hydroxycitronellal, Helional, Cinnamaldehyde and so on.

    As an example the Schiffís Base formed from Hydroxycitronellal and Methyl Anthranilate is Aurantiol - so the odour note would go from lily-of-the-valley to more like orange flower - quite a change.
    ďBattle cries and champagne just in time for sunrise.
    ― David Bowie
    Chris Bartlett
    Perfumes from the edge . . .

    Fine fragrances hand made in The Shire
    Quality perfume making ingredients
    Twitter: @PellWallPerfume
    If you are looking for a perfumery consultation Iím happy to quote: if you want free advice, thatís what these forums are for
    You can also join my blog for more info about perfumes and perfumery.

  5. #5

    Default Re: dimethyl anthranilate vs methyl anthranilate

    Be careful if you buy Dimethyl Anthranilate, or where you source it. The main reason I used to use it was because it wouldn't discolour; especially useful if you are making a candle fragrance. One batch that was bought, caused discolouration and when we GC'd it, it was found to be 50.0% Dimethyl Anthranilate and 50.0% Methyl Anthranilate, thus defeating the purpose it was bought for. Make quite sure you have what you asked for.

  6. #6

    Default Re: dimethyl anthranilate vs methyl anthranilate

    What could be a good test? I guess reacting it with something cheap that forms a colored base with ease? Maybe vanillin?

  7. #7

    Default Re: dimethyl anthranilate vs methyl anthranilate

    Quote Originally Posted by Nizan View Post
    What could be a good test? I guess reacting it with something cheap that forms a colored base with ease? Maybe vanillin?
    Vanillin would be effective - the Schiffís Base with methyl anthranilate is almost black. If I remember correctly the ethyl vanillin equivalent is bright red, so that would probably work well too.
    ďBattle cries and champagne just in time for sunrise.
    ― David Bowie
    Chris Bartlett
    Perfumes from the edge . . .

    Fine fragrances hand made in The Shire
    Quality perfume making ingredients
    Twitter: @PellWallPerfume
    If you are looking for a perfumery consultation Iím happy to quote: if you want free advice, thatís what these forums are for
    You can also join my blog for more info about perfumes and perfumery.

  8. #8

    Default Re: dimethyl anthranilate vs methyl anthranilate

    Quote Originally Posted by Nizan View Post
    What could be a good test? I guess reacting it with something cheap that forms a colored base with ease? Maybe vanillin?
    The best way would be to get it GC'd. If that isn't possible, reacting it with Hydroxycitronellal should do. Methyl Anthranilate reacts with Hydroxycitronellal very quickly at room temperature, and as both are liquid you have no problems with dissolving one in the other.
    Last edited by David Ruskin; 24th July 2017 at 09:57 AM.

  9. #9

    Default Re: dimethyl anthranilate vs methyl anthranilate

    Quote Originally Posted by David Ruskin View Post
    The best way would be to get it GC'd. If that isn't possible, reacting it with Hydroxycitronellal should do. Methyl Anthranilate reacts with Hydroxycitronellal very quickly at room temperature, and as both are liquid you have know problems with dissolving one in the other.
    Talk about discoloritation... i wanna ask.. I have made aurantiol by my self with 15 min 30 min 1,23,4 hours modification time. But when it is heating at 90'C in 2, 3 and 4 hours the color of aurantiol is darkening. What caused of color darkening? GC give the result that rasio of metil antranilat increasing. Are increasing of metil antraniat caused changing color? Thanksss

  10. #10
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    Default Re: dimethyl anthranilate vs methyl anthranilate

    All schiff bases change color from clear, to mostly yellow. Some dark brown or even black.
    Change in color is one of the key signs to know that the reaction is, or has taken place.
    Paul Kiler
    PK Perfumes
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    Gold Medal for "Best Aroma"; Los Angeles Artisan Fragrance Salon

  11. #11

    Default Re: dimethyl anthranilate vs methyl anthranilate

    Dimethyl anthranilate is essential for making a synthetic mandarin - it has a striking mandarin note to it compared to the heavier and sweeter (to my nose) methyl anthranilate. Also dimethyl anthranilate has a light mustiness that is absent from methyl anthranilate.

  12. #12

    Default Re: dimethyl anthranilate vs methyl anthranilate

    I have always thought that Dimethyl Anthranilate smells of old books.

    Cooking anything at 90įC for several hours will not do any good. Aurantiol should be a deep, clear yellow. Treating it to such temperatures for so long, will not result in a useable product.

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