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ChemicalBook >> CAS DataBase List >>trans-Anethole

trans-Anethole

CAS No.
4180-23-8
Chemical Name:
trans-Anethole
Synonyms
ANETHOLE;trans-Anethol;(E)-1-Methoxy-4-(prop-1-en-1-yl)benzene;(E)-anethole;FEMA 2086;P-PROPENYLANISOLE;4-trans-propenyl-anisole;1-METHOXY-4-PROPENYLBENZENE;PARA METHOXY ALPHA PHENYL PROPENE;ANETHOLUM
CBNumber:
CB3228733
Molecular Formula:
C10H12O
Molecular Weight:
148.2
MDL Number:
MFCD00009284
MOL File:
4180-23-8.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-05-28 01:03:22
Product description Number Pack Size Price
trans-Anethole ≥99%, FCC, FG W208604 1 each $58
Anethol natural, 99%, FG W208620 1 each $65.7
trans-Anethole ≥99%, FCC, FG W208604 1kg $143
Anethol natural,99%,FG W208620 1kg $245
trans-Anethole ≥99%, FCC, FG W208604 5kg $437
More product size

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.)
FLAVIS Number 04.010 | 1-Methoxy-4-(prop-1(trans)-enyl)benzene
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
biological source synthetic
Water Solubility practically insoluble
Sensitive Light Sensitive
Merck 14,643
JECFA Number 217
BRN 774229
Stability Light sensitive
Major Application flavors and fragrances
InChI 1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+
InChIKey RUVINXPYWBROJD-ONEGZZNKSA-N
SMILES COc1ccc(\C=C\C)cc1
LogP 3.388
CAS DataBase Reference 4180-23-8(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS) TRANS-ANETHOLE
EWG's Food Scores 1
FDA UNII Q3JEK5DO4K
NIST Chemistry Reference Anethole(4180-23-8)
EPA Substance Registry System (E)-Anethole (4180-23-8)
UNSPSC Code 85151701
NACRES NA.24

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)Environment (GHS09)
GHS07,GHS09
Signal word  Warning
Hazard statements  H317-H411
Precautionary statements  P261-P272-P273-P280-P302+P352-P333+P313
PPE dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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  TSCA listed
HS Code  29093090
Storage Class 10 - Combustible liquids
Hazard Classifications Aquatic Chronic 2
Skin Sens. 1
Toxicity LD50 orally in Rabbit: 2090 mg/kg LD50 dermal Rabbit > 5000 mg/kg
REACH Registrations Active
NFPA 704
1
1 0

trans-Anethole price More Price(103)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich W208604 trans-Anethole ≥99%, FCC, FG 4180-23-8 1 each $58 2026-04-30 Buy
Sigma-Aldrich W208620 Anethol natural, 99%, FG 4180-23-8 1 each $65.7 2026-04-30 Buy
Sigma-Aldrich W208604 trans-Anethole ≥99%, FCC, FG 4180-23-8 1kg $143 2026-04-30 Buy
Sigma-Aldrich W208620 Anethol natural,99%,FG 4180-23-8 1kg $245 2026-04-30 Buy
Sigma-Aldrich W208604 trans-Anethole ≥99%, FCC, FG 4180-23-8 5kg $437 2026-04-30 Buy
Product number Packaging Price Buy
W208604 1 each $58 Buy
W208620 1 each $65.7 Buy
W208604 1kg $143 Buy
W208620 1kg $245 Buy
W208604 5kg $437 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).

References

[1] M. B. EMBONG S M D Hadziyev. ESSENTIAL OILS FROM SPICES GROWN IN ALBERTA. ANISE OIL (PIMPINELLA ANISUM)[C]//57 1. 1977: 681-688. DOI: 10.4141/cjps77-100
[2] KEN-ICHI FUJITA  Isao K. Potentiation of fungicidal activities of trans-anethole against Saccharomyces cerevisiae under hypoxic conditions[J]. Journal of bioscience and bioengineering, 2004, 98 6: Pages 490-492. DOI: 10.1016/s1389-1723(05)00318-x
[3] MADDALENA DONATI . Radical scavenging and antimicrobial activities of Croton zehntneri, Pterodon emarginatus and Schinopsis brasiliensis essential oils and their major constituents: estragole, trans-anethole, β-caryophyllene and myrcene[J]. Natural Product Research, 2015, 29 10: Pages 939-946. DOI: 10.1080/14786419.2014.964709

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

trans-Anethole Preparation Products And Raw materials

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View Lastest Price from trans-Anethole manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
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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)-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) trans-Anethole, 98.5%, from Foeniculum vulgare Mill.
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