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cis-Anethol Basic information Product Name: cis-Anethol Synonyms: PARA ALPHA PHENYL PROPENE;P-PROPENYLBENZENE;P-PROPENYLPHENYL METHYL R;TRANS-1--4-(1-PROPENYL)BENZENE;TRANS-P-PROPENYLBENZENE;TRANS-P-PROPENYLANISOLE;FEMA 2086;(E)-1--4-(1-PROPENYL)BENZENE CAS: 104-46-1 MF: C10H12O MW: 148.2 EINECS: 203-205-5 Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors Mol File: 104-46-1.mol   cis-Anethol Chemical Properties Melting point 20-21 °C(lit.) Boiling point 234-237 °C(lit.) density 0.988 g/mL at 25 °C(lit.) refractive index n20/D 1.561(lit.) Fp 195 °F storage temp. 2-8°C Water Solubility 148.2mg/L(25 ºC) Stability: Stable. Combustible. Incompatible with strong oxidizing agents. CAS DataBase Reference 104-46-1(CAS DataBase Reference) NIST Chemistry Reference Benzene, 1--4-(1-propenyl)-(104-46-1) EPA Substance Registry System Anethole (104-46-1)   Safety Information Hazard Codes Xi,Xn Risk Statements 43-36/37/38-20/21/22 Safety Statements 36/37-36-26 WGK Germany 2 RTECS BZ9275000 F 8 Hazardous Substances Data 104-46-1(Hazardous Substances Data) MSDS Information Provider Language cis-Anethol English ACROS English SigmaAldrich English ALFA English   cis-Anethol Usage And Synthesis Description Anethole is the main component of anise, star anise and fennel oils. It is used in the food and cosmetic industries, in bleaching colors photography and as an embedding material. Is mainly a cause of intolerance to toothpaste but may cause contact dermatitis in food handlers. Chemical Properties Anethole occurs both as its (Z)-[25679-28-1] and (E)-[4180-23-8] isomers in nature; however, (E)-anethole is always the main isomer. Anethole occurs in anise oil (80–90%), star anise oil (>90%), and fennel oil (80%). (E)-Anethole forms colorless crystals (mp 21.5°C) with an anise-like odor and a sweet taste. Anethole is oxidized to anisaldehyde (e.g., with chromic acid); when hydrogenated, it is converted into l--4-propylbenzene. Chemical Properties White crystals; sweet taste; odor of oil of anise. Affected by light. Soluble in 8 vol- umes of 80% alcohol, 1 volume of 90% alcohol; almost immiscible with water. Uses Promote the white blood cells proliferation Definition ChEBI: A monobenzene that is benzene substituted by a prop-1-en-1-yl group at position 4. Preparation Production. Anethole is isolated from anethole-rich essential oils as well as from sulfate turpentine oils or is synthesized starting from anisole. 1) Anethole can be obtained from oils in which it occurs as a major component (main source is star anise oil) by distillation and/or crystallization. 2) A fraction of American sulfate turpentine oil (0.5% of the total) consists mainly of an azeotropic mixture of anethole and caryophyllene. (E)-Anethole can be isolated from this mixture by crystallization. 3) Another fraction of American sulfate turpentine oil (1% of the total) consists essentially of an azeotropic mixture of estragole (l--4-allylbenzene, bp101.3 kPa 216°C) and α-terpineol. Treatment with potassium hydroxide yields a mixture of anethole isomers and ??-terpineol, which can be separated by fractional distillation. 4) Synthesis from anisole and propionic acid derivatives. Anisole is converted into 4-propiophenone by Friedel–Crafts acylation with propionyl chloride or propionic anhydride. The ketone is hydrogenated to the corresponding alcohol with a copper chromite catalyst.The alcohol is dehydrated in the presence of acidic catalysts to a (Z)-/(E)-mixture of anetholes. General Description White crystals or a liquid. Odor of anise oil and a sweet taste. Air & Water Reactions Slightly water soluble . Reactivity Profile Protect from light . Health Hazard ACUTE/CHRONIC HAZARDS: Toxic. Fire Hazard cis-Anethol is combustible. Contact allergens Anethole is the main component of anise, star anise, and fennel oils. It is used in perfumes, food and cosmetic industries (toothpastes), bleaching colors, and photography, and as an embedding material. Safety Profile Poison by ingestion. Questionable carcinogen with experimental tumorigenic data. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also RS.   cis-Anethol Preparation Products And Raw materials Raw materials Sodium hydroxide-->Sodium-->Anisole-->p-Anisaldehyde-->Allyl bromide-->Propionic anhydride-->Dimethyl r-->1,4-Dibenzene-->Sodium propionate-->Crotonic acid-->4-Bromoanisole-->4-Phenyl-1-butene-->Allylbenzene-->4-Allylanisole-->Fennel Oil-->Anise oil Preparation Products p-Anisaldehyde-->Anethole trithione-->trans-Anethole-->HEXESTROL-->4-N-PROPYLANISOLE