아네톨

한글명:아네톨

카스 번호104-46-1

상품명:cis-Anethol

CBNumberCB0228732

분자식C10H12O

포뮬러 무게148.2

MOL 파일104-46-1.mol

동의어(한글)

아네토레

아네톨

아니스장뇌

화학적 성질

녹는점	20-21 °C(lit.)
끓는 점	234-237 °C(lit.)
밀도	0.988 g/mL at 25 °C(lit.)
굴절률	n20/D 1.561(lit.)
인화점	195 °F
저장 조건	Sealed in dry,2-8°C
용해도	DMSO: 30 mg/ml; PBS (pH 7.2): 10 mg/ml
물리적 상태	기름
색상	Colorless to off-white
냄새	100.00%에서. 달콤한 아니스 감초 약용
?? ??	감초
수용성	148.2mg/L(25℃)
안정성	안정적인. 타기 쉬운. 강한 산화제와 호환되지 않습니다.
LogP	3.39
CAS 데이터베이스	104-46-1(CAS DataBase Reference)
NIST	Benzene, 1-methoxy-4-(1-propenyl)-(104-46-1)
EPA	Anethole (104-46-1)

위험 및 안전 성명

위험품 표기

Xi,Xn

위험 카페고리 넘버

43-36/37/38-20/21/22

안전지침서

36/37-36-26

WGK 독일

RTECS 번호

BZ9275000

F 고인화성물질

유해 물질 데이터

104-46-1(Hazardous Substances Data)

NFPA 704:

	2
0		0

그림문자(GHS)

아네톨 MSDS

아네톨 화학적 특성, 용도, 생산

개요
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.
화학적 성질
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.
물리적 성질
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.
역사
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.
용도
Promote the white blood cells proliferation
정의
ChEBI: A monomethoxybenzene that is methoxybenzene substituted by a prop-1-en-1-yl group at position 4.
제조 방법
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.
일반 설명
White crystals or a liquid. Odor of anise oil and a sweet taste.
공기와 물의 반응
Slightly water soluble .
반응 프로필
Protect from light .
건강위험
ACUTE/CHRONIC HAZARDS: Toxic.
화재위험
cis-Anethol is combustible.
색상 색인 번호
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.
Pharmacology
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.
Clinical Use
As a drug, anethole is mainly used for leukopenia caused by tumor chemotherapy.
Safety Profile
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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