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Sigma-Aldrich

trans-Anethole

99%

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Synonym(s):
4-Propenylanisole, trans-1-Methoxy-4-(1-propenyl)benzene
Linear Formula:
CH3CH=CHC6H4OCH3
CAS Number:
4180-23-8
Molecular Weight:
148.20
Beilstein:
774229
EC Number:
224-052-0
MDL number:
MFCD00009284
UNSPSC Code:
12352100
PubChem Substance ID:
24847351
NACRES:
NA.22

Quality Level

200

Assay

99%

form

solid or liquid

refractive index

n20/D 1.561 (lit.)

bp

234-237 °C (lit.)

mp

20-21 °C (lit.)

solubility

H2O: very slightly soluble
acetone: soluble
alcohol: freely soluble
benzene: soluble
carbon disulfide: soluble
chloroform: miscible
diethyl ether: miscible
ethyl acetate: soluble
petroleum ether: soluble

density

0.988 g/mL at 25 °C (lit.)

SMILES string

COc1ccc(\C=C\C)cc1

InChI

1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+

InChI key

RUVINXPYWBROJD-ONEGZZNKSA-N

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General description

trans-Anethole is the chief component of several essential oils including star anise, anise seed oil and sweet fennel. It is a commercial flavor substance in baked goods, candy,ice cream, chewing gum, and alcoholic beverages.

Application

trans-Anethole was used as carbon and energy supplement in the culture media of Pseudomonas putida strain, JYR-1 .

Biochem/physiol Actions

Major metabolite of trans-anethole in human volunteers was 4-methoxyhippuric acid. It can be metabolized by a Arthrobacter strain (TA13).
Naturally occurring phenylpropene derivative that is estrogenic at lower concentrations and cytotoxic at higher concentrations to cancer cell lines. The cytotoxicity is related to the metabolism of trans-anethole to 4-hydroxy-1-propenylbenzene.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H317,H411

Hazard Classifications

Aquatic Chronic 2 - Skin Sens. 1

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Jiyoung Ryu et al.
Journal of agricultural and food chemistry, 53(15), 5954-5958 (2005-07-21)
Bacterial strain JYR-1, which utilizes high concentrations (up to 100 mM) of trans-anethole as the sole source of carbon and energy, was isolated from soil. It grew to OD(600)(nm) = 2.6 with a doubling time of 8 h when grown
S A Sangster et al.
Xenobiotica; the fate of foreign compounds in biological systems, 17(10), 1223-1232 (1987-10-01)
1. The metabolic fates of the naturally occurring food flavours trans-anethole and estragole, and their synthetic congener p-propylanisole, have been investigated in human volunteers using the [methoxy-14C]-labelled compounds. The doses used were close to those encountered in the diet, 1
Rajesh K Joshi et al.
Natural product communications, 6(1), 141-143 (2011-03-04)
The essential oil of the leaves of Feronia elephantum Corr. was analyzed by gas chromatography and gas chromatography/mass spectrometry. The main constituents were beta-pinene (28.4%), Z-anethole (22.1%), methyl chavicol (12.0%) and E-anethole (8.1%), among thirty-three identified compounds, which represented 92.6%
Bülent Cetin et al.
Journal of medicinal food, 13(1), 196-204 (2010-02-09)
The objective of this study was to determine the chemical compositions of the essential oil and hexane extract isolated from the inflorescence, leaf stems, and aerial parts of Florence fennel and the antimicrobial activities of the essential oil, hexane extract
Eun Jeong Choo et al.
Biological & pharmaceutical bulletin, 34(1), 41-46 (2011-01-08)
Anethole is known to possess anti-inflammatory and anti-tumor activities and to be a main constituent of fennel, anise, and camphor. In the present study, we evaluated anti-metastatic and apoptotic effects of anethole on highly-metastatic HT-1080 human fibrosarcoma tumor cells. Despite
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