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221074

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

Name: <I>cis</I>-2,4,5-Trimethoxy-1-propenylbenzene
Brand: ALDRICH

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:

5273-86-9

Molecular Weight:

208.25

EC Number:

226-096-6

UNSPSC Code:

12352100

PubChem Substance ID:

24853209

Beilstein/REAXYS Number:

1910605

MDL number:

MFCD00009281

NACRES:

NA.22

Assay:

70%

Form:

liquid

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Properties

Quality Level

100

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

Description

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

GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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One step conversion of toxic beta-asarone from Acorus calamus into 1-(2,4,5-trimethoxyphenyl)-1,2-dihydroxypropane and asaronaldehyde occurring in Piper clusii.

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

A mild and convenient procedure for the conversion of toxic beta-asarone into rare phenylpropanoids: 2,4,5-trimethoxycinnamaldehyde and gamma-asarone.

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.

Antifungal activity of beta-asarone from rhizomes of Acorus gramineus.

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

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Global Trade Item Number

SKU	GTIN
221074-1G	04061838776877