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221074

Sigma-Aldrich

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

70%

Sinonimo/i:

β-Asarone, cis-1-Propenyl-2,4,5-trimethoxybenzene, cis-Asarone, cis-Isoasarone

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About This Item

Formula condensata:
(CH3O)3C6H2CH=CHCH3
Numero CAS:
5273-86-9
Peso molecolare:
208.25
Beilstein:
1910605
Numero CE:
226-096-6
Numero MDL:
MFCD00009281
Codice UNSPSC:
12352100
ID PubChem:
24853209

Livello qualitativo

100

Saggio

70%

Stato

liquid

Indice di rifrazione

n20/D 1.558 (lit.)

Densità

1.073 g/mL at 25 °C (lit.)

Stringa SMILE

[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-
RKFAZBXYICVSKP-WAYWQWQTSA-N

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Descrizione generale

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

Applicazioni

cis-2,4,5-Trimethoxy-1-propenylbenzene (β-Asarone) was used in preparation of:
  • 2,4,5-trimethoxycinnamaldehyde and 2,4,5-trimethoxycinnamyltosylhydrazone[2]
  • 1-(2,4,5-trimethoxyphenyl)-1,2-dihydroxypropane[3]

Altre note

Remainder trans (α-asarone)

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H302

Classi di pericolo

Acute Tox. 4 Oral

Codice della classe di stoccaggio

10 - Combustible liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

235.4 °F - closed cup

Punto d’infiammabilità (°C)

113 °C - closed cup

Dispositivi di protezione individuale

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

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Certificati d'analisi (COA)

Lot/Batch Number
STBJ5237
STBJ4351
STBJ3856
STBG3974V
STBG2813V

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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
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
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
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