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trans-Anethole

trans-Anethole Structure
trans-Anethole
  • CAS No.4180-23-8
  • Chemical Name:trans-Anethole
  • CBNumber:CB3228733
  • Molecular Formula:C10H12O
  • Formula Weight:148.2
  • MOL File:4180-23-8.mol
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
  • PH :7 (H2O)
  • Water Solubility  :practically insoluble
  • Sensitive  :Light Sensitive
  • Merck  :14,643
  • JECFA Number :217
  • BRN  :774229
  • InChIKey :RUVINXPYWBROJD-ONEGZZNKSA-N
  • 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)
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
  • F  :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
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordWarning
  • Hazard statements H317-H303-H411
  • Precautionary statements P273-P261-P280g-P302+P352a-P321-P333+P313-P501a-P280
trans-Anethole Price More Price(31)
  • Brand: Sigma-Aldrich
  • Product number: 8.00429
  • Product name : trans-Anethole
  • Purity: for synthesis
  • Packaging: 100 mL
  • Price: $99.9
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: W208604
  • Product name : trans-Anethole
  • Purity: ≥99%, FCC, FG
  • Packaging: 1 kg
  • Price: $123
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: 8.00429
  • Product name : trans-Anethole
  • Purity: for synthesis
  • Packaging: 250 mL
  • Price: $138.75
  • Updated: 2021/03/22
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  • Brand: Sigma-Aldrich
  • Product number: 00130595
  • Product name : trans-Anethole
  • Purity: primary pharmaceutical reference standard
  • Packaging: 100mg
  • Price: $284
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: W208604
  • Product name : trans-Anethole
  • Purity: ≥99%, FCC, FG
  • Packaging: 5 kg
  • Price: $367
  • Updated: 2021/03/22
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trans-Anethole Chemical Properties,Usage,Production

  • 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 expectorant, gastric stimulant, insecticide
  • Uses platelet aggregation inhibitor
  • Preparation By isomerization of estragole using alcoholic potassium hydroxide as agent (Arctander, 1969).
  • 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%.
  • 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
  • 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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  • High purity trans-Anethole 4180-23-8 kf-wang(at)kf-chem.com
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