DP
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B-asarone Synthesis
I'm wondering how hard it would be to synthesize B-asarone and what would be the best precursor to start with. If anyone has a synthesis or can
get the refs below please post them here... thanks.
Seshadri, Thiruvengadam,
Proc. Indian Acad. Sci. 32A, 110 (1950)
Sharma, Dandiya,
Indian J. Appl. Chem. 32, 236 (1969)
Stereospecific synthesis of b-asarone
M. T. S. Hsia et al.,
177th Am. Chem. Soc. Meet. (Honolulu, April 1979)
[Edited on 6-8-2005 by DP]
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Sergei_Eisenstein
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I think I have read the first reference, but it was years ago. Anyhow, they used the Elbs persulfate reaction and yields were low.
There are a few ways to obtain beta-asarone. Which route is the most convenient depends on your access to not-OTC chemical substances. The Wittig
reaction of asaraldehyde would be a very convenient lab procedure. Another route would involve Claisen rearrangement of allyloxy-3,4-dimethoxybenzene
(from veratraldehyde in 2 steps). Yet another method would use a FC acylation of 1,2,4-trimethoxybenzene, reduce the obtained propiophenone to the
corresponding alcohol and dehydrate the latter to beta-asarone.
Et cetera.
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praseodym
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What do you want asarone for since it is banned in many countries??
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Sergei_Eisenstein
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| Quote: | Originally posted by praseodym
What do you want asarone for since it is banned in many countries?? |
Not completely true. I believe it is still present in several soft drinks and spirits, just like safrole. Essential oils with high asaron content are
just not allowed anymore for use in pharmaceutical preparations.
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DP
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Hhhmm... I guess I'll just stick to distilling calamus oil since my access to non-OTC chems is not too good at the present time. This is
basically a profit thing... I would like to sell the B-asarone and then sell the asarone-free calamus oil. As long as the B-asarone is not used for
any foodstuffs its fine to sell it in the US and many small perfume manufactures etc would probably be interested.
[Edited on 7-8-2005 by DP]
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Odin
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| Quote: | Originally posted by DP
Hhhmm... I guess I'll just stick to distilling calamus oil since my access to non-OTC chems is not too good at the present time. This is
basically a profit thing... I would like to sell the B-asarone and then sell the asarone-free calamus oil. As long as the B-asarone is not used for
any foodstuffs its fine to sell it in the US and many small perfume manufactures etc would probably be interested.
[Edited on 7-8-2005 by DP] |
Thats a hell of alot of calamus as you need the root and rhizome 'cause the stalk and leaves do not contain any b-asarone. B-asarone naturally
is a mild stimulant
You would have to harvest over 1000 plants just for that purpose.
And who would you sell b-asarone to anyways? Alex Shulgin
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CherrieBaby
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gamma-asarone (2,4,5-trimethoxy-allylbenzene), anyone?
Vargas, Pardini & Viertler; Tetrahedron Lett. 30, pp 4037-4040, 1989.
Abstract: gamma-asarone is synthesised in high yield (~ 80%), and conveniently, by anodic methoxylation of methyl eugenol, at constant current. The
method is extremely simple and inexpensive.
Procedure: The electrolyses were performed in an undivided cell using a Pt foil anode (2.5 x 3.5 cm) and a W wire as cathode. A solution of methyl
eugenol (2.8 mmoles) in MeOH (60 mL) containing NaClO4 (6.0 mmoles) and NaOH (30.0 mmoles) was electrolysed at room temperature (50 mA, 0.0057 Acm-1
3F/mol). After completion, MeOH was removed under reduced pressure [because of the possible formation of explosive perchlorates the mixture should NOT
be taken to complete dryness]. Water added to the residue, the mixture acidulated with HCl until pH 4 and extracted with ether. After concentrating
under vacuum, gamma-Asarone was isolated by column chromatography (SiO2, Hex-EtAc 3:2) and fully characterised; spectral data as per literature. When
5.6 mmoles of methyl eugenol were used, under otherwise similar conditions, gamma-asarone was obtained in lower yield (55%).
[Edited on 30-11-2005 by CherrieBaby]
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CherrieBaby
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Electrosynthesis of γ-Asarone
R.R. Vargas, V.L. Pardini and H. Viertler
Tetrahedron Lett. 30, pp 4037-4040, 1989.
Abstract: γ-Asarone is synthesised in high yield, and conveniently, by anodic methoxylation of methyl eugenol, at constant
current. The method is extremely simple and inexpensive.
Attachment: electrosynth.gamma-Asarone_TL.30,p4037-40,1989_OCR.pdf (76kB)
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Mush
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Quote: Originally posted by DP  |
Seshadri, Thiruvengadam,
Proc. Indian Acad. Sci. 32A, 110 (1950)
[Edited on 6-8-2005 by DP] |
Proceedings of the Indian Academy of Sciences, Section A , Volume 32, p 110-113, (1950)
Nuclear oxidation in flavones and related compounds. Part XXX. A new synthesis of asarone — T. R. Seshadri and T. R. Thiruvengadam
http://www-old.ias.ac.in/j_archive/proca/32/vol32contents.ht...
[Edited on 24-2-2017 by Mush]
Attachment: Seshadri, Thiruvengadam - Proc. Indian Acad. Sci. 32A, 110 (1950).rar (468kB)
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Mush
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Synthesis and Some Pharmacological Actions of Asarone
P. K Shanna and P. C. Dandiya
Indian J. Appl. Chem. V.32, p.236; (1969)
Attachment: phpcubrWV (2.4MB)
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