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
Beilstein/REAXYS Number:
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)
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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
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.
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
Daijie Wang et al.
Journal of separation science, 34(23), 3339-3343 (2011-11-01)
In this study, supercritical fluid extraction (SFE) was used to extract essential oil from Acorus tatarinowii Schott under the pressure of 25 MPa and temperature of 35°C. Two (E)- and (Z)-diastereomers of α-asarone and β-asarone were separated and purified by
Jadwiga Marczewska et al.
Acta poloniae pharmaceutica, 70(2), 349-354 (2013-04-26)
In our previous paper we examined mutagenic and genotoxic activity of 4 alpha-asarone isomers 2-5 exhibiting relatively high hypolipidemic activity. In the present paper, we examined genotoxic activity of alpha-asarone and its isomers as the ability to damage cellular DNA
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