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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:
5273-86-9
Molecular Weight:
208.25
Beilstein:
1910605
EC Number:
226-096-6
MDL number:
MFCD00009281
UNSPSC Code:
12352100
PubChem Substance ID:
24853209

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

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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
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Divyasree Sandeep et al.
Mutation research, 722(1), 62-68 (2011-03-29)
α-Asarone (1-propenyl-2,4,5-methoxybenzol), one of the active components of Acorus calamus extract, was examined for its efficacy as a radioprotector in mice exposed to lethal and sublethal whole-body γ-radiation. Oral administration of α-asarone 1h prior to the radiation exposure reduced radiation
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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