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Merck
CN

221074

Sigma-Aldrich

cis-2,4,5-Trimethoxy-1-propenylbenzene

70%

Synonym(s):

β-Asarone, cis-1-Propenyl-2,4,5-trimethoxybenzene, cis-Asarone, cis-Isoasarone

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About This Item

Linear Formula:
(CH3O)3C6H2CH=CHCH3
CAS Number:
Molecular Weight:
208.25
Beilstein:
1910605
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
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Quality Level

Assay

70%

form

liquid

refractive index

n20/D 1.558 (lit.)

density

1.073 g/mL at 25 °C (lit.)

SMILES string

[H]\C(C)=C(/[H])c1cc(OC)c(OC)cc1OC

InChI

1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3/b6-5-

InChI key

RKFAZBXYICVSKP-WAYWQWQTSA-N

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General description

cis-2,4,5-Trimethoxy-1-propenylbenzene is an antibiotic and was isolated from the extract of Acorus gramineus using various chromatographic procedures.

Application

cis-2,4,5-Trimethoxy-1-propenylbenzene (β-Asarone) was used in preparation of:
  • 2,4,5-trimethoxycinnamaldehyde and 2,4,5-trimethoxycinnamyltosylhydrazone
  • 1-(2,4,5-trimethoxyphenyl)-1,2-dihydroxypropane

Other Notes

Remainder trans (α-asarone)

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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A K Sinha et al.
Natural product letters, 15(6), 439-444 (2002-02-13)
1-(2,4,5-Trimethoxyphenyl)-1,2-dihydroxypropane (2), a natural phenylpropanoid occurring in Piper clusii, has been synthesized for the first time from toxic beta-asarone (1) of Acorus calamus with osmium tetroxide, while 1 with osmium tetroxide (catalytic amount) in presence of sodium metaperiodate furnished the
Jee Yeon Lee et al.
Journal of agricultural and food chemistry, 52(4), 776-780 (2004-02-19)
An antifungal substance was isolated from the extract of Acorus gramineus using various chromatographic procedures. The antibiotic was identified as beta-asarone, cis-2,4,5-trimethoxy-1-propenylbenzene, on the basis of the high-resolution EI-mass, NMR, and UV spectral data. Beta-asarone completely inhibited mycelial growth of
Arun K Sinha et al.
Journal of natural products, 65(5), 764-765 (2002-05-25)
Oxidation of beta-asarone (2) with DDQ gave trans-2,4,5-trimethoxycinnamaldehyde (3), which on treatment with p-toluenesulfonyl hydrazine provided corresponding alpha,beta-unsaturated hydrazone derivative (4). Reduction of 4 with sodium borohydride in acetic acid afforded gamma-asarone (1) in 43% yield.
Ying Hu et al.
Drug delivery, 18(1), 84-89 (2010-10-14)
A transdermal drug delivery system has been reported that can increase the bioavailability, reduce the administration duration, and maintain the concentration of drug in blood. In the present study, drug-in-adhesive transdermal patches of α-asarone using Eudragit E100 as pressure-sensitive adhesives
Deepa Bisht et al.
Natural product research, 25(20), 1993-1998 (2011-06-29)
Hydro-distilled essential oils extracted from three commercially important aromatic plants were analysed by capillary gas chromatography-flame ionization detector and gas chromatography/quadrupole mass spectrometry and subjected to antifungal activity. Fifteen compounds, which accounted for 97.8% of Acorus calamus root oil composition

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