| Identification | More | [Name]
trans-Anethole | [CAS]
4180-23-8 | [Synonyms]
1-(4-METHOXYPHENYL)-1-PROPENE
1-METHOXY-4-(1-PROPENYL)BENZENE
1-METHOXY-4-((E)-PROPENYL)-BENZENE
1-METHOXY-4-PROPENYLBENZENE
4-PROPENYLANISOLE
ANETHOLE
ANETHOLE, TRANS-
ANETHOLUM
(E)-1-METHOXY-4-(1-PROPENYL)BENZENE
FEMA 2086
PARA METHOXY ALPHA PHENYL PROPENE
P-METHOXYPROPENYLBENZENE
P-PROPENYLANISOLE
P-PROPENYLPHENYL METHYL ETHER
TRANS-1-METHOXY-4-(1-PROPENYL)BENZENE
TRANS-ANETHOLE
TRANS-P-METHOXYPROPENYLBENZENE
TRANS-P-PROPENYLANISOLE
(E)-1-Methoxy-4-propenyl-benzene
(E)-Anethol | [EINECS(EC#)]
224-052-0 | [Molecular Formula]
C10H12O | [MDL Number]
MFCD00009284 | [Molecular Weight]
148.2 | [MOL File]
4180-23-8.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to pale yellow liquid | [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 | [refractive index ]
n20/D 1.561(lit.)
| [Fp ]
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 | [JECFA Number]
217 | [Merck ]
14,643 | [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]
4180-23-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R43:May cause sensitization by skin contact. | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
UN 3077 9 / PGIII | [WGK Germany ]
2
| [RTECS ]
BZ9275000
| [F ]
8 | [TSCA ]
Yes | [HS Code ]
29093090 | [Toxicity]
LD50 orally in Rabbit: 2090 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
| Hazard Information | Back Directory | [Description]
(E)-Anethol is a phenylpropanoid that has been found in P. anisum seed oil and has antifungal and antioxidant activity.1,2,3 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.2,3 (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.3 | [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]
expectorant, gastric stimulant, insecticide | [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]
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). | [Solubility in organics]
Miscible with alcohol and oils, poorly soluble in Propylene glycol and Glycerin.
| [storage]
Store at -20°C | [Dosage]
The FDA "White List" permits the use of Anise oil in concentrations up to 3500 ppm. (Anise oil contains more than 90% Anethole).
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