dimethyl anthranilate vs methyl anthranilate

gecko214

Well-known member
May 7, 2010
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?
 

Chris Bartlett

Basenotes Plus
Basenotes Plus
Jul 17, 2011
I don’t 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 Schiff’s 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 that’s 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 - that’s because the former is photo-toxic.
 

gecko214

Well-known member
May 7, 2010
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.
 

Chris Bartlett

Basenotes Plus
Basenotes Plus
Jul 17, 2011
No problem.

Don’t forget though that it isn’t 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 Schiff’s 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.
 

David Ruskin

Well-known member
May 28, 2009
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.
 

Nizan

Well-known member
Nov 15, 2013
What could be a good test? I guess reacting it with something cheap that forms a colored base with ease? Maybe vanillin?
 

Chris Bartlett

Basenotes Plus
Basenotes Plus
Jul 17, 2011
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 Schiff’s 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.
 

David Ruskin

Well-known member
May 28, 2009
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.
 
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Sucindryati

New member
Mar 19, 2017
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
 

pkiler

Basenotes Plus
Basenotes Plus
Dec 5, 2007
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.
 

jfrater

Well-known member
Jun 2, 2005
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.
 

David Ruskin

Well-known member
May 28, 2009
I have always thought that Dimethyl Anthranilate smells of old books.

Cooking anything at 90°C 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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