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trans-Anethole

Product Name
trans-Anethole
CAS No.
4180-23-8
Chemical Name
trans-Anethole
Synonyms
ANETHOLE;trans-Anethol;(E)-anethole;(E)-1-Methoxy-4-(prop-1-en-1-yl)benzene;P-PROPENYLANISOLE;4-trans-propenyl-anisole;FEMA 2086;PARA METHOXY ALPHA PHENYL PROPENE;ANETHOLUM;1-METHOXY-4-PROPENYLBENZENE
CBNumber
CB3228733
Molecular Formula
C10H12O
Formula Weight
148.2
MOL File
4180-23-8.mol
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trans-Anethole Property

Melting point:
20-21 °C(lit.)
Boiling point:
234-237 °C(lit.)
Density 
0.988 g/mL at 25 °C(lit.)
vapor pressure 
1.33 hPa (63 °C)
FEMA 
2086 | TRANS-ANETHOLE
refractive index 
n20/D 1.561(lit.)
Flash point:
195 °F
storage temp. 
2-8°C
solubility 
Soluble in benzene, ethyl acetate, acetone, carbon disulfide.
form 
Liquid After Melting
color 
Clear colorless to pale yellow
Odor
at 10.00 % in dipropylene glycol. sweet anise licorice mimosa
PH
7 (H2O)
Odor Type
licorice
Water Solubility 
practically insoluble
Sensitive 
Light Sensitive
Merck 
14,643
JECFA Number
217
BRN 
774229
Stability:
Light sensitive
InChIKey
RUVINXPYWBROJD-ONEGZZNKSA-N
LogP
3.388
CAS DataBase Reference
4180-23-8(CAS DataBase Reference)
NIST Chemistry Reference
Anethole(4180-23-8)
EPA Substance Registry System
(E)-Anethole (4180-23-8)
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Safety

Hazard Codes 
Xi,N
Risk Statements 
43-51/53
Safety Statements 
36/37-61
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
2
RTECS 
BZ9275000
8
TSCA 
Yes
HS Code 
29093090
Toxicity
LD50 orally in Rabbit: 2090 mg/kg LD50 dermal Rabbit > 5000 mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H317May cause an allergic skin reaction

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
W208620
Product name
Anethol
Purity
natural,99%,FG
Packaging
1kg
Price
$239
Updated
2024/03/01
Sigma-Aldrich
Product number
W208620
Product name
Anethol
Purity
natural,99%,FG
Packaging
5kg
Price
$958
Updated
2024/03/01
Sigma-Aldrich
Product number
W208604
Product name
trans-Anethole
Purity
≥99%, FCC, FG
Packaging
1kg
Price
$134
Updated
2024/03/01
Sigma-Aldrich
Product number
W208604
Product name
trans-Anethole
Purity
≥99%, FCC, FG
Packaging
5kg
Price
$412
Updated
2024/03/01
Sigma-Aldrich
Product number
W208604
Product name
trans-Anethole
Purity
≥99%, FCC, FG
Packaging
10Kg
Price
$658
Updated
2024/03/01
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trans-Anethole Chemical Properties,Usage,Production

Description

(E)-Anethol is a phenylpropanoid that has been found in P. anisum seed oil and has antifungal and antioxidant activity. It is active against fermentatively growing S. cerevisiae under hypoxic, but not normoxic, conditions (MIC = 100 μg/ml), and against C. parapsilosis when used at a concentration of 15% w/w. (E)-Anethol has antioxidant activity in a Trolox equivalent antioxidant capacity (TEAC) assay but does not scavenge 2,2-diphenyl-1-picrylhydrazel (DPPH) radicals in a cell-free assay.

Chemical Properties

trans-anethole is a clear colorless to pale yellow liquid and has a characteristic anise, sweet, spicy, warm odor and corresponding sweet taste.

Anethole (1-methoxy-4-propenyl-benzene, isoestragole) is an alkoxypropenylbenzene derivative and an important favoring component of essential oils of more than 20 plant species. Essential oils from seeds of anise (Pimpinellaanisum L.), star anise (Illicium verum Hook.f), and sweet fennel (Foeniculum vulgare Mill. var. dulce) are the main sources used for the isolation of anethole. Two isomers of anethole occur in nature: E- or trans-anethole and Z-or cis-anethole. About 90 % of natural anethole is trans-isomer. Besides separation from natural essential oils, anethole is obtained using the rectification of crude sulfate turpentine and/or the organic synthesis starting from methylchavicol or anisole and propionic anhydride. Compared to natural compound, synthetic trans-anethole is impurified with higher amounts of cis-isomer.

Occurrence

Anethole is methyl ether of oestrone and has been found in fennel, aniseed, coriander, and many other volatile oils.

Uses

flavoring agent in food, dentifrices, etc.; in perfumery for soap, etc.; in pharmaceuticals as flavor; in photography and in embedding materials in microscopy; some perfumery uses (fennei; absinthe; Hyacinth jacinthe; detergents; magnolia). Natural occurrence: star anise

Uses

expectorant, gastric stimulant, insecticide

Uses

platelet aggregation inhibitor

Uses

trans-Anethole is used to inhibits lung and forestomach carcinogenesis, used as carbon and energy supplement in the culture media of Pseudomonas putida strain. It is also used as used as a flavoring substance.

Definition

ChEBI: Anethole is a monomethoxybenzene that is methoxybenzene substituted by a prop-1-en-1-yl group at position 4. It has a role as a plant metabolite.

Preparation

By esterification of p-cresol with methyl alcohol and with subsequent condensation with α-cetaldehyde (Perknis); the most common method of preparation is from pine oil. By fractional distillation of the essential oils of anise, star anise, and fennel; the anise essences contain an average of 85% anethole; fennel, from 60 to 70%.

Preparation

By isomerization of estragole using alcoholic potassium hydroxide as agent (Arctander, 1969).

Taste threshold values

Taste characteristics at 10 ppm: sweet, anise, licorice and spicy with a lingering, sweet aftertaste.

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 1797, 1985 DOI: 10.1021/jo00211a002
Tetrahedron, 24, p. 2183, 1968 DOI: 10.1016/0040-4020(68)88120-7

General Description

trans-Anethole is a naturally occuring flavouring agent. It has insecticidal, larvicidal, and antimicrobial properties.

Biochem/physiol Actions

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.

Anticancer Research

It is one of the major constituents of essential oil of fennel and anise and belongs tothe class of phenylpropenes. It has the capacity to block both inflammation andcarcinogenesis. It is an antioxidant and also a suppressor of NF-κB activation byIκBα degradation (Aggarwal and Shishodia 2004).

Metabolism

Anethole is metabolized by oxidation of the propenyl group and is excreted as anisic acid (Williams, 1959). The metabolism of trans-anethole used in the preparation of anis-flavoured alcoholic beverages was studied in the rabbit and rat after iv and oral administration. It was excreted rapidly from the animal regardless of the method of administration. After iv injection it was found concentrated in the liver, lungs and brain; after oral administration, absorption was slight and most of it remained in the stomach. Ethyl alcohol has no effect on the metabolism (Le Bourhis, 1968).

trans-Anethole Preparation Products And Raw materials

Raw materials

Preparation Products

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trans-Anethole Suppliers

Ji 'an trillion spice oil co. LTD
Tel
0796-0796-8110986 18979610200
Email
1053756189@qq.com
Country
China
ProdList
113
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58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
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76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
4006608290; 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40241
Advantage
62
Chembest Research Laboratories Limited
Tel
021-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6013
Advantage
61
Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30132
Advantage
84
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24539
Advantage
81
Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44751
Advantage
61
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202 13764082696;
Email
info@hanhongsci.com
Country
China
ProdList
42982
Advantage
64
jiliang chemicals
Tel
21-62165282 15801962796;
Fax
021 61153784
Email
bidingchem@163.com
Country
China
ProdList
1157
Advantage
60
Shandong Xiya Chemical Co., Ltd
Tel
4009903999 13355009207
Fax
0539-6365991
Email
3007715519@qq.com
Country
China
ProdList
18736
Advantage
57
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View Lastest Price from trans-Anethole manufacturers

Wuhan Xinhao Biotechnology Co., Ltd
Product
trans-Anethole 4180-23-8
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100ton
Release date
2024-03-19
WUHAN FORTUNA CHEMICAL CO., LTD
Product
trans-Anethole 4180-23-8
Price
US $0.00-0.00/kg
Min. Order
25kg
Purity
99%
Supply Ability
10000kg
Release date
2023-01-14
Anhui Zhongda Biotechnology Co., Ltd
Product
trans-Anethole 4180-23-8
Price
US $0.00-0.00/g
Min. Order
1g
Purity
99%
Supply Ability
100000tons
Release date
2023-08-14

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