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．nD201.559．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.
アネトール 上流と下流の製品情報
原材料
準備製品