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 n
- Flash point:195 °F
- storage temp. Sealed in dry,2-8°C
- Water Solubility 148.2mg/L(25 ºC)
- Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
- CAS DataBase Reference104-46-1(CAS DataBase Reference)
- NIST Chemistry ReferenceBenzene, 1-methoxy-4-(1-propenyl)-(104-46-1)
- EPA Substance Registry SystemAnethole (104-46-1)
cis-Anethol Usage And Synthesis
- DescriptionAnethole 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 PropertiesAnethole 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.
- Chemical PropertiesWhite 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.
- Physical propertiesAppearance: this compound shows a colorless or light-yellow liquid appearance. Melting point: 20–21?°C. Solubility: dissolve in chloroform and ether in unlimited amount; soluble in benzene, ethyl acetate, acetone, carbon disulfide, petroleum ether, and alcohol; insoluble in water. It has a sweet smell.
- HistoryIn China, anise has been used as a traditional food spice and seasoning. In the anise
plant, the main biological active ingredient is volatile oils such as trans-anethole.
Till the end of last century, several methods to obtain the pure anethole have been
1. Cooling, crystallizing, and recrystallizing after the distillation of the anise oil.
2. Heating p-methoxyphenyl crotonic acid at 220–240?°C.
3. Heating and dehydrating the derived product of anisaldehyde and C2H5MgX.
4. Heating anisaldehyde together with propionic anhydride and sodium propionate.
5. Adding concentrated hydrochloric acid and phosphoric acid to the mixture of anisole and propionaldehyde at 0?°C and then heating the product with pyridine to remove hydrogen chloride.
6. Prepare Grignard reagent using parabromoanisole, then react with allyl bromide to produce p-methoxyphenylpropylene, then heat with potassium hydroxide, and finally anethole was obtained after isomerization.
7. Using crystalline ferric chloride to catalyze the reaction of p-propenyl phenol and methanol .
Anethole is easily oxidized when exposed in the air, especially in the presence of heat, light, or catalyst . Therefore, in recent years, a series of studies have been carried out on the synthesis of its derivatives in order to obtain more active substances.
- UsesPromote the white blood cells proliferation
- DefinitionChEBI: A monomethoxybenzene that is methoxybenzene substituted by a prop-1-en-1-yl group at position 4.
- PreparationProduction. 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.
- General DescriptionWhite crystals or a liquid. Odor of anise oil and a sweet taste.
- Air & Water ReactionsSlightly water soluble .
- Reactivity ProfileProtect from light .
- Health HazardACUTE/CHRONIC HAZARDS: Toxic.
- Fire Hazardcis-Anethol is combustible.
- Contact allergensAnethole 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.
- PharmacologyAnethole is the main ingredient in star anise oil and possesses a variety of pharmacological effects.
1. Increasing the white blood cellular activity. Some agents such as Shengbaining and Shengxuening, whose main active ingredients were extracted from the star anise, can promote mature white blood cells in the bone marrow to spread into the surrounding blood. Due to the body’s own feedback, mature and release speed of bone marrow cells were accelerated. It can also keep bone marrow cells’ activity, enhancing the white blood cells (especially granulocytes).
2. Bacteriostatic effect. Star anise oil shows antibacterial effects in a variety of strains including Staphylococcus aureus, Escherichia coli, Bacillus subtilis, Aspergillus niger, Aspergillus flavus, Penicillium citrinum, yeast, Shigella, diphtheria bacillus, and Salmonella typhi. The results laid a theoretical foundation for the development and utilization of novel plant-derived antifungal propenylbenzene derivatives.
3. Antiviral effects . Star anise oil can act on different acyclovir-susceptible and acyclovir-resistant herpes simplex virus type 1 (HSV-1) strains.
4. Other effects. Anethole can improve the activity of anticholinesterase . It shows significant inhibitory effect against acetylcholinesterase and butyrylcholinesterase, and the IC50 value was 39.89±0.32?μg/mL and 75.35±1.47?μg/mL, while the value for star anise oil was 36.00±0.44?μg/mL and 70.65±0.96?μg/ mL, respectively. It has also been reported that anethole has an antioxidant effect.
Through structural transformation, a variety of compounds can be prepared from anethole. Anisaldehyde, produced by the oxidation reaction, was widely used in the preparation of flavors for its lasting aroma. On the other hand, it can also be used as the intermediate during the preparation of drugs such as amoxicillin.
- Clinical UseAs a drug, anethole is mainly used for leukopenia caused by tumor chemotherapy.
- Safety ProfilePoison 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
- Preparation ProductsAnisic aldehydeAnethole trithionetrans-AnetholeHEXESTROL4-N-PROPYLANISOLE
- Raw materialsSodium hydroxideSodiumAnisoleAnisic aldehydeAllyl bromidePropionic anhydrideDimethyl ether1,4-DimethoxybenzeneSodium propionateCrotonic acid4-Bromoanisole4-Phenyl-1-butene Allylbenzene4-AllylanisoleGALANGAL ROOT OILAnise oil
- 3,4-Dimethoxycinnamonitrile RESCINNAMINE 4-Methoxycinnamic acid 3-Hydroxy-4-methoxycinnamic acid 4-METHOXYCINNAMONITRILE 1-CYANO-1-PHENYL-2-(4-METHOXY-PHENYL)ETHYLENE ISOSAFROLE AFLATOXIN G1 trans-2,4,5-Trimethoxycinnamic acid m-Anisyl alcohol ANETHOL NATURAL POLYANETHOLESULFONIC ACID SODIUM SALT Methoxy cis-Anethol (Trifluoromethoxy)benzene Anise oil 4-Methoxyphenylacetic acid 4-Methoxybenzyl cyanide
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