221074
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
EC Number:
226-096-6
UNSPSC Code:
12352100
PubChem Substance ID:
Beilstein/REAXYS Number:
1910605
MDL number:
NACRES:
NA.22
Assay:
70%
Form:
liquid
InChI key
RKFAZBXYICVSKP-WAYWQWQTSA-N
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-
SMILES string
[H]\C(C)=C(/[H])c1cc(OC)c(OC)cc1OC
assay
70%
form
liquid
refractive index
n20/D 1.558 (lit.)
density
1.073 g/mL at 25 °C (lit.)
Quality Level
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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
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.
Other Notes
Remainder trans (α-asarone)
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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.
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
Qi-Xiong Chen et al.
Biological & pharmaceutical bulletin, 36(1), 23-30 (2012-10-19)
For centuries, extracts of Acorus gramineus have been used extensively in traditional Chinese medicine for the treatment, management, and/or control of human ailments, including central nervous system disorders such as convulsions and epilepsy. In the present study, we investigated the
Zhenwei Yu et al.
AAPS PharmSciTech, 14(1), 294-300 (2013-01-12)
A hot-melt, pressure-sensitive adhesive (HMPSA) based on styrene-isoprene-styrene was prepared, and its compatibility with various transdermal penetration enhancers was investigated. The effect of penetration enhancers on the adhesion properties of HMPSA was also studied. A drug-in-adhesive patch was formulated using
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