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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:
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. Peracid oxidation of isosafrole yields isomers of 2,4-dimethyl-3,5-bis(3,4-methylenedioxyphenyl)tetrahydrofuran. Encapsulated vanadyl compounds in Y-zeolite pores catalyzed isosafrol oxidation under microwave irradiation was reported.

Application

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315

Hazard Classifications

Acute Tox. 4 Oral - Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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A Pastrakuljic et al.
Biochemical pharmacology, 53(4), 531-538 (1997-02-21)
Ethoxyresorufin O-deethylation (EROD) has been used as a specific probe for CYP1A1 and CYP1A2. Selective inhibition of one of these cytochromes P450 may differentiate their activity in human liver. Four inhibitors were chosen to examine the selective inhibition of EROD
Catalytic isosafrol oxidation mediated by impregnated and encapsulated vanadyl-Y-zeolite under microwave irradiation.
Alvarez HM, et al.
Applied Catalysis A: General, 326(1), 82-88 (2007)
Catalytic oxidation of isosafrol by vanadium complexes.
Alvarez HM, et al.
Catalysis Communications, 8(9), 1336-1340 (2007)
M T Donato et al.
Drug metabolism and disposition: the biological fate of chemicals, 23(5), 553-558 (1995-05-01)
The dealkylations of 7-ethoxy- and 7-pentoxyresorufin,p-nitrophenol hydroxylation, and regio- and stereoselective hydroxylation of testosterone were measured to study the stability and inducibility of cytochrome P450 activities in cultured human hepatocytes. The results showed that human hepatocytes in primary culture retain
M Swist et al.
Forensic science international, 149(2-3), 181-192 (2005-03-08)
In our study 1-(3,4-methylenedioxyphenyl)-2-propanone (MDP-2-P or PMK) was prepared by two different routes, i.e. by oxidizing isosafrole in an acid medium and by 1-(3,4-methylenedioxyphenyl)-2-nitropropene reduction. The final product-MDP-2-P was subjected to GC/MS analysis. The intermediates and reaction by-products were identified
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