cis-Anethol Chemical Properties
- Melting point:
- 20-21 °C(lit.)
- Boiling point:
- 234-237 °C(lit.)
- 0.988 g/mL at 25 °C(lit.)
- refractive index
- Flash point:
- 195 °F
- storage temp.
- Water Solubility
- 148.2mg/L(25 ºC)
- Stable. Combustible. Incompatible with strong oxidizing agents.
- CAS DataBase Reference
- 104-46-1(CAS DataBase Reference)
- NIST Chemistry Reference
- Benzene, 1-methoxy-4-(1-propenyl)-(104-46-1)
- EPA Substance Registry System
- Anethole (104-46-1)
cis-Anethol Usage And Synthesis
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.
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-methoxy-4-propylbenzene.
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ChEBI: A monomethoxybenzene that is methoxybenzene substituted by a prop-1-en-1-yl group at position 4.
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-methoxy-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-methoxypropiophenone 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.
White crystals or a liquid. Odor of anise oil and a sweet taste.
Air & Water Reactions
Slightly water soluble .
Protect from light .
ACUTE/CHRONIC HAZARDS: Toxic.
cis-Anethol is combustible.
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.
Poison by ingestion. Questionable carcinogen with experimental tumorigenic data. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ETHERS.
cis-Anethol Preparation Products And Raw materials
- 3,4,5-TRIMETHOXYCINNAMIC ACID
- AFLATOXIN G1
- trans-2,4,5-Trimethoxycinnamic acid
- m-Anisyl alcohol
- ANETHOL NATURAL
- 4-Methoxybenzyl alcohol
- POLYANETHOLESULFONIC ACID SODIUM SALT
- Anise oil
- 4-Methoxyphenylacetic acid
- 4-Methoxybenzyl cyanide
- Anisic acid
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