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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
Molecular Weight:
148.2
MDL Number:
MFCD00009284
MOL File:
4180-23-8.mol
MSDS File:
SDS
Last updated:2024-10-25 16:21:11

trans-Anethole Properties

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
PH 7 (H2O)
Odor at 10.00 % in dipropylene glycol. sweet anise licorice mimosa
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
Substances Added to Food (formerly EAFUS) TRANS-ANETHOLE
CAS DataBase Reference 4180-23-8(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII Q3JEK5DO4K
NIST Chemistry Reference Anethole(4180-23-8)
EPA Substance Registry System (E)-Anethole (4180-23-8)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS09
Signal word  Warning
Hazard statements  H317-H411
Precautionary statements  P261-P272-P273-P280-P302+P352-P333+P313
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
NFPA 704
1
1 0

trans-Anethole price More Price(50)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich W208620 Anethol natural,99%,FG 4180-23-8 1kg $239 2024-03-01 Buy
Sigma-Aldrich W208620 Anethol natural,99%,FG 4180-23-8 5kg $958 2024-03-01 Buy
Sigma-Aldrich W208604 trans-Anethole ≥99%, FCC, FG 4180-23-8 1kg $134 2024-03-01 Buy
Sigma-Aldrich W208604 trans-Anethole ≥99%, FCC, FG 4180-23-8 5kg $412 2024-03-01 Buy
Sigma-Aldrich W208604 trans-Anethole ≥99%, FCC, FG 4180-23-8 10Kg $658 2024-03-01 Buy
Product number Packaging Price Buy
W208620 1kg $239 Buy
W208620 5kg $958 Buy
W208604 1kg $134 Buy
W208604 5kg $412 Buy
W208604 10Kg $658 Buy

trans-Anethole Chemical Properties,Uses,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
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

platelet aggregation inhibitor

Uses

expectorant, gastric stimulant, insecticide

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.

Dosage

The FDA "White List" permits the use of Anise oil in concentrations up to 3500 ppm. (Anise oil contains more than 90% Anethole).

140-67-0
4180-23-8
Synthesis of trans-Anethole from Estragole

trans-Anethole Preparation Products And Raw materials

Global( 456)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Mojin Biotechnology Co., Ltd
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+undefined86-15315557071 sales02@sdzhonghuimaterial.com China 983 58

View Lastest Price from trans-Anethole manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Synthetic Anethole pictures 2024-10-31 Synthetic Anethole
4180-23-8
US $70.00 / kg 1kg 99 5000 Hebei Zhuanglai Chemical Trading Co.,Ltd
trans-Anethole pictures 2024-10-31 trans-Anethole
4180-23-8
US $30.00 / kg 1kg 99% 5000kg/Month Hebei Zhuanglai Chemical Trading Co.,Ltd
trans-Anethole pictures 2024-10-31 trans-Anethole
4180-23-8
US $0.00-0.00 / kg 25kg 99% 10000kg WUHAN FORTUNA CHEMICAL CO., LTD
  • trans-Anethole pictures
  • trans-Anethole
    4180-23-8
  • US $30.00 / kg
  • 99%
  • Hebei Zhuanglai Chemical Trading Co.,Ltd
  • trans-Anethole pictures
  • trans-Anethole
    4180-23-8
  • US $0.00-0.00 / kg
  • 99%
  • WUHAN FORTUNA CHEMICAL CO., LTD
trans-Anethole, 98+%, stab. trans-Anethole, 98.5% trans-Anethole trans-Anethole, stabilized (E)-1-METHOXY-4-(1-PROPENYL)BENZENE 1-methoxy-4-(1-propenyl)-,(E)-Benzene anethole (E) Anistearoptene trans-Anisecamphor trans-anisol 4-PROPENYLANISOLE ANETHOLE, TRANS- 1-METHOXY-4-((E)-PROPENYL)-BENZENE 1-METHOXY-4-(1-PROPENYL)BENZENE 1-(4-METHOXYPHENYL)-1-PROPENE P-METHOXYPROPENYLBENZENE P-PROPENYLPHENYL METHYL ETHER TRANS-P-PROPENYLANISOLE TRANS-P-METHOXYPROPENYLBENZENE TRANS-ANETHOLE (E)-Anethol (e)-p-propenylanisole ANETHOL EXTRA USP 21/22 FCC ANETHOL USP, NATURAL ANETHOLE, DAB 10 TRANS-ANETHOLE 99+% FCC ANETHOLE, TERPENE STANDARD FOR GC Anethol99%ForSynthesis trans-4-Propenyl-anisol trans-Anetholetrans-4-Propenyl-anisol ANETHOLE NATURAL Benzene, 1-methoxy-4-(1E)-1-propenyl- (E)-1-Methoxy-4-propenyl-benzene Anethole,98% anis camphor ANETHOL NATUERLICH AUS ANISOEL ANETHOLE N.F. 4-Propenylanisole, trans-1-Methoxy-4-(1-propenyl)benzene 4-Propenylanisole, trans-1-Methoxy-4-(1-propenyl)benzene, Anetholum trans-1-(4-Methoxyphenyl)-1-propene trans-1-p-Anisylpropene TRANS-P-METHOXY-BETA-METHYLSTYRENE trans-Anethole,4-Propenylanisole, trans-1-Methoxy-4-(1-propenyl)benzene Anethole (2 mL) (AS) (E)-1-(4-Methoxyphenyl)-1-propene 1-Methoxy-4-[(E)-1-propenyl]benzene 4-[(E)-1-Propenyl]anisol 4-[(E)-1-Propenyl]phenyl methyl ether trans-Anethole,99% trans-Anethole, 99% 100ML trans-Anethole, 99% 5ML trans-p-Methoxypropenylbenzene trans-p-Propenylanisole TRANS-ANETHOLE FOR SYNTHESIS 250 ML TRANS-ANETHOLE FOR SYNTHESIS 100 ML trans-Anethole(synthetic) Trans-Anethole (Synonyms: (E)-Anethole) High purity trans-Anethole 4180-23-8 kf-wang(at)kf-chem.com Trans-Anethole ((E)?-Anethole)