Anethole
Anethole
CAS: 104-46-1
Molecular Formula: C10H12O
Anethole - Names and Identifiers
Anethole - Physico-chemical Properties
| Molecular Formula | C10H12O |
| Molar Mass | 148.2 |
| Density | 0.988g/mLat 25°C(lit.) |
| Melting Point | 20-21°C(lit.) |
| Boling Point | 234-237°C(lit.) |
| Flash Point | 195°F |
| Water Solubility | 148.2mg/L(25 ºC) |
| Solubility | Almost insoluble in water, miscible with ether and chloroform, soluble in benzene, ethyl acetate, acetone, carbon disulfide and petroleum ether. |
| Appearance | Colorless or yellowish liquid or crystal |
| Storage Condition | Sealed in dry,2-8°C |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| Refractive Index | n20/D 1.561(lit.) |
| MDL | MFCD00009284 |
| Physical and Chemical Properties | Colorless or yellowish liquid or crystal. The melting point is 22.5 °c, the boiling point is 235 °c, 81-81.5 °c (307Pa), the relative density is 0.9883(20/4 °c), the refractive index is 1.56145, and the flash point is 90 °c. With chloroform, ether miscible, soluble in benzene, ethyl acetate, acetone, carbon disulfide, petroleum ether and alcohol, insoluble in water. With a sweet taste, with a special aroma of fennel. |
| Use | For daily chemical, medicine, food |
Anethole - Risk and Safety
| Risk Codes | R43 - May cause sensitization by skin contact R36/37/38 - Irritating to eyes, respiratory system and skin. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S36/37 - Wear suitable protective clothing and gloves. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 2 |
| RTECS | BZ9275000 |
| FLUKA BRAND F CODES | 8 |
Anethole - Upstream Downstream Industry
| Raw Materials | Fennel oil |
Anethole - Reference
| Reference Show more | 1. Zhao Xinghe, Huang Jia, Liu Yuping. Determination of Key Aroma Components in Beijing Dry Yellow Sauce by Solid Phase Microextraction Combined with Gas-Mass Spectrometry [J]. Food and Fermentation Industry, 2018, 044(003):266-272. 2. Dong Xiaoke, Liu Jinmin, Li Zhonghao, Yuan Siyuan, Wang Kaiyue, Li Lili, Zheng Xiangchun. Study on the main blood components of Chaibei Zhixian Decoction in rats and its pharmacokinetics [J]. Global Chinese medicine, 2021,14(03):377-383. 3. [IF = 2.858] Tian-Tian Li et al."Control of pathogenic fungi on Panax notoginseng by volatile oils from the food ingredients Allium sativum and Foeniculum vulgare." LETTERS IN APPLIED MICROBIOLOGY. 2022 Apr 06 |
Anethole - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| application | anethole has a special fennel smell and corresponding sweetness, and can be used for flavoring all foods, especially pastry foods. It is also a raw material for the manufacture of anisaldehyde, anisole, and the synthetic drug-negative hormone hexanestrol. Fennel can be used in large quantities for the preparation of fennel essence, licorice essence, bayberry essence, etc., as well as toothpaste, gargle, cosmetics, soap, etc. |
| anise | anise is native to southern and southwestern Guangxi in China. only the western part of Fangcheng county and debao county each account for 1/4 of the country's output. Taiwan, Fujian, Guangdong, Guizhou, Yunnan, Zhejiang and other provinces are also cultivated. Anise is an evergreen tree, up to 20 meters high; the bark is gray to reddish brown. Single leaves alternate, leathery, lanceolate to oblong, 5~12cm long, 1.5~5cm wide, shortly pointed or shortly acuminate at the top, narrowly cuneate at the base, glossy and transparent oil spots on the top, sparsely pilose below; petiole stout, about 1cm long. Flowers open in spring, solitary leaf axils, fleshy perianth; sepals 3, yellow-green; petals 6~9, arranged in 2~3 rounds, light pink or dark red, broad-oval or oblong; stamens 11~20 pieces, arranged in 2~3 rounds; carpels 8~9 pieces, separated, short style, thick base, small stigma. Aggregate fruits are arranged in a star shape, 2.5~3.5cm in diameter, mature carpels reddish brown. Seeds oblate, brown, shiny. The flowering period is twice a year. Spring fruit harvest period is from January to February, autumn fruit period is from August to September, mainly autumn fruit. The main use of anise oil in the fragrance industry is to separate the anise brain, as the starting material for the preparation of anisaldehyde, anisol, anisic acid and its esters, and also used for food Flavors and toothpaste, tooth powder and wine, candy, beverages and tobacco are used in small amounts in daily flavors. The anise fruit is also a common seasoning and spice. It has the effects of appetizing qi, warming the kidneys and dispelling cold in medicine. Fennel oil is the main raw material for the synthesis of the negative hormone hexanestrol in medicine. |
| pharmacological effects | anethole has obvious effect of increasing white blood cells, mainly neutrophils. Its function is to promote the maturation and release of bone marrow cells into the peripheral blood. |
| ozonation to prepare anisaldehyde | natural anise brain naturally exists in the essential oil of star anise and fennel. it has the smell of fennel, spice and licorice. it is often used in vanilla, fennel, cherry and mint essence. it is a food spice approved by the Chinese GB2760-1996 for use. the recommended dosage is about 11-1500mg/kg in the final flavored food. Anisaldehyde was prepared by ozonation with anisole as raw material and a mixture of acetic acid and cyclohexane as solvent. The effects of solvent, ozonation time, dosage of reducing agent, reduction decomposition time and reduction temperature on the reaction results were investigated, and the order of ozonation reaction was preliminarily discussed. The optimized process conditions are as follows: excellent (acetic acid): excellent (cyclohexane) = 1:4, ozonation time 100min,n(NaHSOs)/bamboo (anethole) = 1.1, reduction decomposition time 60min, reduction temperature 80 ℃. Under these conditions, the yield of the product is ≥ 84% and the purity is ≥ 98%. Journal of Qingdao University of Science and Technology 2007 Issue 2 School of Chemical Engineering, Qingdao University of Science and Technology |
| use | used as fennel essence and licorice essence in the fragrance of food, especially cakes; It is also used in beverages, and is also widely used in apricot, quince, bayberry and other flavors, toothpaste and gargle. In addition, anethole is also used for flavoring agents and odorants of drugs, spices of cosmetics and soaps, raw materials of synthetic drugs and sensitizers of color photography. As a drug, anethole has a certain therapeutic effect on leukopenia caused by chemotherapy or radiotherapy, and leukopenia caused by other reasons. The consumption proportion of anisole as the production of anisaldehyde is larger. In the presence of p-aminobenzenesulfonic acid, anethole (or essential oil containing anethole) is oxidized by ozone, nitric acid, potassium permanganate or red alum sulfuric acid to obtain anisaldehyde (p-methoxybenzaldehyde). It is used as flavor and spice for toothpaste, and also used in food, medicine, etc. Used in daily chemical, medicine, and food |
| production methods | anethole has many industrial methods, and the following are introduced. (1) The fennel oil or anise oil is cooled, crystallized, distilled and recrystallized with alcohol. It is also possible to rectify fennel oil and collect distilled matter at 230-234°C. Or vacuum distillation, collect 142 ℃(5.60kPa) or 110 ℃(2.7kPa) fraction, that is, anethole. (2) It is obtained by heating p-methoxyphenylbutenoic acid at 220-240°C. (3) Heat p-propenyl anisole with caustic and isomerize to anethole. (4) obtained by methylation of p-propenyl phenol. (5) anisaldehyde acts with G2H5MgX to dehydrate the product by heating water to obtain anisole. (6) anisaldehyde is heated with propionic anhydride and sodium propionate to obtain anisole. (7) In the mixture of anisole and propionaldehyde, concentrated hydrochloric acid and phosphoric acid are added at 0°C to saturate the hydrogen chloride gas, and the product is heated with pyridine to remove hydrogen chloride to obtain anisole. Hydrobromic acid can also be used instead of concentrated hydrochloric acid. The product is treated with metallic sodium, and anethole is obtained by debromination. (8) p-bromoanisole is prepared into a Grignard reagent, and it reacts with allyl bromide to generate p-methoxyphenylpropene, which is then heated with potassium hydroxide to isomerize to obtain anethole. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:01:54
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Raw Materials for Anethole