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Sigma-Aldrich

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

70%

Synonym(e):

β-Asaron, cis-1-Propenyl-2,4,5-trimethoxy-benzol, cis-Asaron, cis-Isoasaron

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About This Item

Lineare Formel:
(CH3O)3C6H2CH=CHCH3
CAS-Nummer:
5273-86-9
Molekulargewicht:
208.25
Beilstein:
1910605
EG-Nummer:
226-096-6
MDL-Nummer:
MFCD00009281
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24853209

Assay

70%

Form

liquid

Brechungsindex

n20/D 1.558 (lit.)

Dichte

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-

InChIKey

RKFAZBXYICVSKP-WAYWQWQTSA-N

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Allgemeine Beschreibung

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

Anwendung

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

Sonstige Hinweise

Remainder trans (α-asarone)

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

H-Sätze

H302

Gefahreneinstufungen

Acute Tox. 4 Oral

Lagerklassenschlüssel

10 - Combustible liquids

WGK

WGK 3

Flammpunkt (°F)

235.4 °F - closed cup

Flammpunkt (°C)

113 °C - closed cup

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

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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
Zhenwei Yu et al.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 36(21), 2967-2970 (2012-02-09)
To investigate the relationship of properties and drug release rate of hot melt pressure sensitive adhesive (HMPSA), and to provide a recommendation of preparing and selecting of HMPSA for transdermal use. HMPSA with different properties were prepared using styrene-isoprene-styrene triblock
Yong-Qi Fang et al.
Die Pharmazie, 67(2), 120-123 (2012-04-20)
beta-Asarone has significant pharmacological effects on the central nervous system. As a potential therapeutic agent to manage brain diseases, analysis of the pharmacokinetics of beta-asarone in brain is necessary. We used cardio-perfusion method to exclude the beta-asarone in the brain
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