アネトール

危険有害性情報のコード(GHS)

• 絵表示(GHS)

  

• 注意喚起語

  Warning

• 危険有害性情報

  H317：アレルギー性皮膚反応を起こすおそれ

• 注意書き

  P261：粉じん/煙/ガス/ミスト/蒸気/スプレーの吸入を避ける こと。

  P280：保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。

アネトール 価格

MSDS Information

• cis-Anethol

アネトール 化学特性,用途語,生産方法

• 定義

  本品は、次の化学式で表される芳香族エーテルである。

• 溶解性

  水に不溶, エタノール, エーテルに易溶。エタノール及びアセトンに極めて溶けやすく、水にほとんど溶けない。

• 解説

  アネトール．精油成分の一つで，ういきょう油や，だいういきょう油などに含まれる．アニス様の香気をもち，甘味を有する．融点21～23 ℃，沸点232～236 ℃．d²⁵0.988．n_D²⁰1.559．水に難溶．リキュール酒，化粧品，練り歯磨き，アニスアルデヒドの製造などに用いられる．

  アニス特有の香味を有する無色の液体。化学的にはp(パラ)-プロペニルフェニルメチルエーテルとよぶ。冷時固化する。スターアニス油（大茴香油(だいういきょうゆ)）中に多く存在し、この精油を冷却して結晶を分離するか、分留により製造する。また、アニスアルデヒドと臭化エチルマグネシウムとを反応させ、生成物を脱水させて合成する。食品、菓子の香味づけとして多量に用いられる。

  　香辛料の成分として、とくにアニス特有の甘い香りはこの成分による。せっけん香料、口腔(こうくう)剤、リキュールにも使用する。

• 化粧品の成分用途

  変性剤、皮膚コンディショニング剤、香料、香味剤

• 効能

  矯味・矯臭剤

• 説明

  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.

• 化学的特性

  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.

• 物理的性質

  Appearance: 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.

• 来歴

  In 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 developed, including:
  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.

• 使用

  Promote the white blood cells proliferation

• 定義

  ChEBI: A monomethoxybenzene that is methoxybenzene substituted by a prop-1-en-1-yl group at position 4.

• 製造方法

  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, bp_{101.3 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.

• 一般的な説明

  White crystals or a liquid. Odor of anise oil and a sweet taste.

• 空気と水の反応

  Slightly water soluble .

• 反応プロフィール

  Protect from light .

• 健康ハザード

  ACUTE/CHRONIC HAZARDS: Toxic.

• 火災危険

  cis-Anethol is combustible.

• 接触アレルゲン

  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.

• 薬理学

  Anethole 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.

• 臨床応用

  As a drug, anethole is mainly used for leukopenia caused by tumor chemotherapy.

• 安全性プロファイル

  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.

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