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329606

Sigma-Aldrich

Isosafrol

mixture of cis and trans

Synonym(s):

1,2-Methylenedioxy-4-propenylbenzene

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About This Item

Empirical Formula (Hill Notation):
C10H10O2
CAS Number:
120-58-1
Molecular Weight:
162.19
Beilstein/REAXYS Number:
82640
EC Number:
204-410-2
MDL number:
MFCD00005838
UNSPSC Code:
12352100
PubChem Substance ID:
24859803
NACRES:
NA.22

form

liquid

refractive index

n20/D 1.573 (lit.)

bp

77-86 °C/3.5 mmHg (lit.)

density

1.12 g/mL at 25 °C (lit.)

SMILES string

C\C=C\c1ccc2OCOc2c1

InChI

1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2-6H,7H2,1H3/b3-2+

Inchi Key

VHVOLFRBFDOUSH-NSCUHMNNSA-N

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General description

Isosafrol is also referred as 1,2-methylenedioxy-4(1-propenyl)benzene. It is an important intermediate for the synthesis of drugs like L-DOPA.[1] Peracid oxidation of isosafrole yields isomers of 2,4-dimethyl-3,5-bis(3,4-methylenedioxyphenyl)tetrahydrofuran.[2] Encapsulated vanadyl compounds in Y-zeolite pores catalyzed isosafrol oxidation under microwave irradiation was reported.[3]

Application

Isosafrol was used in preparation of 1-(3,4-methylenedioxyphenyl)-2-propanone (MDP-2-P or PMK).[4]

Pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H315

Hazard Classifications

Acute Tox. 4 Oral - Skin Irrit. 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN0830
MKCJ8878
MKCJ2170
MKBZ0058V
MKBS2389V

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M J Leaver et al.
Molecular marine biology and biotechnology, 2(6), 338-345 (1993-12-01)
A full length cDNA coding for cytochrome P450 1A1 was isolated from a plaice liver cDNA library constructed in lambda ZAPII. The deduced amino acid sequence of this cDNA was 78% homologous to that of rainbow trout P450 1A1 and
E I Shvartz et al.
Voprosy meditsinskoi khimii, 44(2), 167-171 (1998-06-23)
The transcription level of CYP2B1/2 gene in the liver of Sprague-Dawley (SD), Brattleboro (BL) and Wistar (W) rats treated with isosafrol (IS), Arochlor 1254 (AC), phenobarbital (PB) and triphenildioxane (TPD) was studied. The quantity of CYP2B1/2 mRNA was assessed by
P H Jellinck et al.
The Journal of steroid biochemistry and molecular biology, 46(6), 791-798 (1993-12-01)
The effect of indole-3-carbinol (IC), an anticarcinogen present in cruciferous vegetables, to alter the metabolism of 4-androstenedione (AD) by female rat liver microsomes was investigated and compared to that of its main gastric conversion product, diindolylmethane (DIM) as well as
C L Miranda et al.
Toxicology and applied pharmacology, 142(1), 123-132 (1997-01-01)
Liver microsomes from juvenile trout metabolized DMBA to unknown highly polar metabolites (X) and to DMBA-t-5,6-diol, DMBA-t-8,9-diol, 7-OHM-12-MBA, 7M-12-OHMBA, 2-OH-DMBA, 4-OH-DMBA, and trace amounts of DMBA-t-3,4-diol. Treatment of trout with beta-naphthoflavone (BNF) and isosafrole (ISF) increased the formation of these
D Taras-Valéro et al.
Environmental and molecular mutagenesis, 32(4), 314-324 (1999-01-09)
Mice of the XVIInc/Z and DBA/2N strains, which are responsive and nonresponsive, respectively, to the aryl hydrocarbon (Ah) receptor, were treated with the hepatocarcinogen 5,9-dimethyldibenzo[c,g]carbazole and their livers were examined by nuclease P1-enhanced 32P-postlabeling for the levels of DNA adducts
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