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Merck

117870

trans-Anethole

99%

Synonym(s):

4-Propenylanisole, trans-1-Methoxy-4-(1-propenyl)benzene

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About This Item

Linear Formula:
CH3CH=CHC6H4OCH3
CAS Number:
4180-23-8
Molecular Weight:
148.20
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24847351
EC Number:
224-052-0
Beilstein/REAXYS Number:
774229
MDL number:
MFCD00009284
Assay:
99%
Form:
solid or liquid

Key Documents

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InChI key

RUVINXPYWBROJD-ONEGZZNKSA-N

InChI

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

SMILES string

COc1ccc(\C=C\C)cc1

assay

99%

form

solid or liquid

Quality Level

200

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.)

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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

signalword

Warning

hcodes

H317,H411

Hazard Classifications

Aquatic Chronic 2 - Skin Sens. 1

Storage Class

10 - Combustible liquids

wgk

WGK 2

flash_point_f

213.8 °F

flash_point_c

101 °C

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN6439
BCCM9388
STBL4085
STBL0897
BCCG0981

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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
Ching Hui Chen et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 19(8-9), 763-767 (2012-04-03)
Many traditional Chinese medicines target the treatment of inflammation which is emerging to be a critical component to cancer development and progression. The key aromatic compound in star anise anethole has demonstrated both anti and pro-cancerous effects depending on the
Josenilda Malveira Cavalcanti et al.
Journal of ethnopharmacology, 144(2), 240-247 (2012-09-25)
Croton zehntneri is a Euphorbiaceae species native to northeastern Brazil, where teas and beverages made from Croton zehntneri leaves are used as healing agents. To our knowledge, there is no experimental study supporting this claim of pharmacological activity. Full-thickness excisional
Meher U Nessa et al.
Anticancer research, 32(11), 4843-4850 (2012-11-17)
Chemopreventative phytochemicals having antitumour and antioxidant properties can overcome problems of chemoresistance and nonspecific toxicity towards normal cells that are associated with platinum-based chemotherapy against cancer. These agents exert their effects by bringing into play numerous cellular proteins that in
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