squirrelwax
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Organic amines for schiff bases in perfumery
I have recently taken an interest in the schiff bases of
methyl anthranilate.
Having searched for other anthranilic esters I have found
that by extending the chain of the alcohol that is bonded
to the anthranilic acid that other scents are created 
What I would love to know is are there other amines other
than anthranilic esters that have nice smells to form
schiff bases with.
Most amines I have encountered smell of ammonia or
dead fish 
Even the matrix has a sence of humour ;P
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squirrelwax
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A beginning to the answer I seek would be of course indole and other substituted
indoles.
Here is an example of a very famous schiff base Giorgio, this page states its
make up with a little bit of a history of were schiff bases
come from.
http://www.nzzfolio.ch/www/d80bd71b-b264-4db4-afd0-277884b93...
of course a lot of us would know them as imines 
Even the matrix has a sence of humour ;P
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jon
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very interesting indeed, that makes something that was off limits, suddenly available to some of us.
this fragrance chemical has a lot of potential uses
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Saerynide
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very interesting
"Microsoft reserves the right at all times to monitor communications on the Service and disclose any information Microsoft deems necessary to...
satisfy any applicable law, regulation or legal process"
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squirrelwax
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Thankyou
But this still leaves me with the question are there other amines
than these two types that smell nice to humans.
Personally I think with todays climate on cancer causing compounds
it would be best to only use the schiff base mentioned above for candles
and products that are not used on humans.
Just about all compounds with benzene rings these days are starting to
be looked down on.
It would also be my mind that to talk about using these products on humans
may just damage there availability due to this reason.
I think there is a great future for a lot of the chemical amateurs that have
kind of lost there way in the cosmetics industry.
Custom aldehydes and ketones are truly the makings of patent driven companies.
Please see if you can dig up some more amines for us to use if you can
cosmetics is something that I find my love for organic chemistry can really
get its teeth into.
Ill keep looking my self I am sure that other amines with ring structures and
esters on the adjacent carbon could be used for this purpose.
[Edited on 8-1-2011 by squirrelwax]
Even the matrix has a sence of humour ;P
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jon
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well mixed with o-toluidine and acetic acid i don't know if it smells great, but it is very agreeable.
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turd
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I don't think so. Since nobody did, let me point out the obvious: indole is not an amine and definitely does not form imines (=Schiff bases)! Only
primary amines can form imines. Secondary amines can only form enamines or iminium salts, AFAIK, but I never got the hang of organics. 
| Quote: | Just about all compounds with benzene rings these days are starting to
be looked down on. |
Total nonsense.
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squirrelwax
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Indolene 50 (I)
base note
Schiff's base of indol & hydroxycitronellal 50%
Floral, Jasmin, Animal
Modified animal, fecal note useful in floral absolute types. Increases the substantivity of a fragrance and provides fixation as well as floralcy.
CAS # 68908-82-7
can use up to 5% of total concentrate
NEXT ;P
As for the benzene thing well some understand what im on about.
Personally im just wanting to be able to make more scents but
some of us here will fuck that for everyone.
o-toluidine is not the go jon.
But having said that the esters of its acid might just do the trick.
Yep I think adding an ester to an aniline is the trick to patents in the future
of cosmetics.
hehe at last love ya turd but im right
[Edited on 11-1-2011 by squirrelwax]
Even the matrix has a sence of humour ;P
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turd
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Not really. Formally this can be considered an enamine. And apparently in the literature the notion of "enamine Schiff base" is
known. But according to the IUPAC: http://goldbook.iupac.org/S05498.html this is not a Schiff base. Just look at the structure. But then, what do I know of organic chemistry?
Edit: Well, actually formally this can be considered an overlap of an imine and an enamine, so Schiff Base has some merit. Still I think it's
far-fetched.
Edit2: Of course if you see it this way, then this is the Schiff base of indoline (=2,3-dihydroindole). Indole can of course not form Schiff bases, it
IS a Schiff base.
| Quote: | | As for the benzene thing well some understand what im on about. |
Well, then what are you on about? Your body is full of molecules containing six-membered aromatic rings. I doubt they are looked down on. Please make
yourself more clear.
[Edited on 11-1-2011 by turd]
[Edited on 11-1-2011 by turd]
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squirrelwax
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It would seem you know more about organic chemistry than I
no wonder you picked turd as a nickname
Ill have to inform the company I got the info from.
Notice they even misspelled indole but hell I don't hold that against people.
Yes I can see what you mean by indole its self being a Schiff base.
With this in view I guess I have to take back my giggle and storm off sulking
back to the sewer were I belong .
Thanx for the correction turd 
Even the matrix has a sence of humour ;P
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Paddywhacker
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You might be able to make the methyl ester of glycine, or of other amino acids, to give you interesting amines to experiment with.
Don't forget to let us know how it works out if you try.
Edit: I'm not sure how you'd go about esterifying glycine. Fischer esterification with an acid catalyst might be problematic. Maybe
transesterification with a high boiling methyl ester and distilling out the lower boiling amine would be the way to go. A quick search hasn't thrown
up any useful protocol.
[Edited on 12-1-2011 by Paddywhacker]
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turd
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Quote: Originally posted by Paddywhacker  | | Edit: I'm not sure how you'd go about esterifying glycine. Fischer esterification with an acid catalyst might be problematic. Maybe
transesterification with a high boiling methyl ester and distilling out the lower boiling amine would be the way to go. A quick search hasn't thrown
up any useful protocol. |
Actually, there's tons of procedures calling for SOCl2 and ROH. I didn't have a closer look, but I guess they make the R-Cl which reacts cleanly with
the aminoacid. MeOH + HCl seems to work as well.
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squirrelwax
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indole is an aromatic amine not a schiff turd.
[Edited on 23-1-2011 by squirrelwax]
Even the matrix has a sence of humour ;P
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atomicfire
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How would one synthesize methyl anthranilate
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