2,4,5-Trimethoxycinnamaldehyde
2_4_5-Trimethoxycinnamaldehyde.png

2,4,5-Trimethoxycinnamaldehyde is the aldehyde form of alpha-asarone and the trans isomer of Cis-2,4,5-Trimethoxycinnamaldehyde.

Psychoactivity

2,4,5-Trimethoxycinnamaldehyde has no known published psychoactivity tests. It's possible that a metabolite of it might be psychoactive. 2,4,5-Trimethoxycinnamaldehyde and alpha-asarone are closely related to the potent psychedelic TMA-2. For more information on TMA-2 visit Erowid.

Natural Sources

2,4,5-Trimethoxycinnamaldehyde has been isolated from the leaves of Alpinia flabellata Ridley[1].

Synthesis

2,4,5-Trimethoxycinnamaldehyde can be been created by mild oxidation of beta-asarone using DDQ[2].

Chemical Properties

Melting Point: 140-142 C[3]
Appearance: Yellow crystals[3]
Synonyms: trans-2,4,5-trimethoxycinnamaldehyde; 2,4,5-trimethoxy cinnamaldehyde; (E)-2,4,5-trimethoxycinnamaldehyde
PubChem Compound ID: 54045441
Molecular Weight: 222.23716 [g/mol]
Molecular Formula: C12H14O4
XLogP3: 1.9
IUPAC Name: 3-(2,4,5-trimethoxyphenyl)prop-2-enal
InChI: InChI=1S/C12H14O4/c1-14-10-8-12(16-3)11(15-2)7-9(10)5-4-6-13/h4-8H,1-3H3
InChIKey: DNAVOCNYHNNEQI-UHFFFAOYSA-N
Canonical SMILES: COC1=CC(=C(C=C1C=CC=O)OC)OC
CAS No: 106128-88-5 (also 99217-06-8)

Bibliography
1. Phenylbutanoid dimers from the leaves of Alpinia flabellata.
Kikuzaki H1, Tesaki S, Yonemori S, Nakatani N.; Phytochemistry. 2001 Jan;56(1):109-14.; PubMed PMID: 11198817
2. A mild and convenient procedure for the conversion of toxic beta-asarone into rare phenylpropanoids: 2,4,5-trimethoxycinnamaldehyde and gamma-asarone.
Sinha AK1, Acharya R, Joshi BP.; J Nat Prod. 2002 May;65(5):764-5.; PubMed PMID: 12027763
3. Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients
Shmuel Yannai; CRC Press, 2003; ISBN 1420068458, 9781420068450
Unless otherwise stated, the content of this page is licensed under Creative Commons Attribution-ShareAlike 3.0 License