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アネトール

Anethole

HCID 637563
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
104-46-1
標準SMILES
C/C=C/c1ccc(OC)cc1
InChIKey
RUVINXPYWBROJD-ONEGZZNKSA-N
分子式
C10H12O
平均分子量
148.2 g/mol
単同位体質量
148.088815

概要

Anethole appears as white crystals or a liquid. Odor of anise oil and a sweet taste. (NTP, 1992)

名称と識別子

優先名称
Anethole
IUPAC
1-methoxy-4-[(E)-prop-1-enyl]benzene
現地名
アネトール
英語名
cis-Anethol
分子式
C10H12O
分子量
148.2

名称と別名

ANETHOLE104-46-1Anise camphorMonasirupAnethol4-PropenylanisoleAnisole, p-propenyl-trans-p-Propenylanisolep-Anethole1-Methoxy-4-(1-propenyl)benzeneAniskampfertrans-1-p-Anisylpropene
名称をさらに表示
4-(1-プロペニル)アニソール1-(1-プロペニル)-4-メトキシベンゼン1-メトキシ-4-(1-プロペニル)ベンゼン1-(4-メトキシフェニル)プロペン4-(1-プロペニル)-1-メトキシベンゼンモナシラップアネトールβ-メチル-4-メトキシスチレンメチル[4-(1-プロペニル)フェニル]エーテル4-メトキシ-1-(1-プロペニル)ベンゼン1-(4-メトキシフェニル)-1-プロペンアニスカンファーp-プロペニルアニソールアノールメチルエーテルアネト-ル1-メトキシ-4-(プロプ-1-エン-1-イル)ベンゼンp-(1-プロペニル)アニソールSYNTHETIC ANETHOLEFEMA 2086IsoestragoleNatural AnetholePARA METHOXY ALPHA PHENYL PROPENEAnethole NatANETHOLE 21/22
Anethole, trans1-methoxy-4-[(E)-prop-1-enyl]benzenep-1-Propenylanisole1-Methoxy-4-propenylbenzene4-MethoxypropenylbenzeneBenzene, 1-methoxy-4-(1-propenyl)-p-Propenylphenyl methyl etherFEMA No. 2086

物性

構造計算による物性

XLogP
3.3
極性表面積
9.2 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
2
重原子数
11
形式電荷
0
複雑度
121

実験および物理化学的性質

Chemical ClassesOther Classes -> Other Aromatic Compounds
DrugsPharmaceuticals
Cosmetics · 2 件

Cosmetics ingredient -> Flavor; Fragrance; Other (Specify)

Denaturant

SpringerMaterials PropertiesBoiling point
Fragrances · 2 件

Fragrance Ingredient (Anethole (isomer unspecified)) -> IFRA transparency List

Fragrance Ingredient (trans-Anethole) -> IFRA transparency List

Pesticides · 2 件

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Not approved

OdorANISE OIL ODOR
TasteSWEET TASTE
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 3 件

0.9882 (NTP, 1992) - Less dense than water; will float

0.9878 @ 20 °C/4 °C

0.983-0.988

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 2.9% (55 of 1880) of reports.

Warning

H317 (95.3%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1880 reports by companies from 19 notifications to the ECHA C&L Inventory.

This chemical does not meet GHS hazard criteria for 6.2% (20 of 321) of reports.

危険有害性情報

Regulatory Information · 6 件

Chemical: Benzene, 1-methoxy-4-(1-propenyl)-

Chemical: Benzene, 1-methoxy-4-(1-propenyl)-, (E)-

Hazard Traits - Fragrance Allergen

Regulation (EC) No 1831/2003 (amended)

Benzene, 1-methoxy-4-(1-propen-1-yl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1-methoxy-4-(1-propen-1-yl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Benzene, 1-methoxy-4-(1E)-1-propen-1-yl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1-methoxy-4-(1E)-1-propen-1-yl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Other Safety InformationIMAP assessments - Benzene, 1-methoxy-4-(1-propenyl)-, (E)-: Human health tier II assessment
DOT LabelCombustible Liquid
Fire HazardsThis compound is combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: Toxic. (NTP, 1992)
Hazards Summary

化学と産業

薬理情報

Metabolism/Metabolites · 3 件

ANETHOLE YIELDS PARA-PROPENYLPHENOL IN RABBIT, MOUSE, GUINEA PIG, & DOG. ANETHOLE YIELDS PARA-PROPENYLPHENOL IN RAT. /FROM TABLE/

ANETHOLE YIELDS ANISIC ACID IN MAN, RABBIT, & RAT. ANETHOLE YIELDS PARA-METHOXYCINNAMYL ALCOHOL IN RAT.

OXIDATIVE O-DEMETHYLATION LEADING TO P-HYDROXYPROPENYLBENZENE & P-HYDROXYCINNAMIC ACID WAS FOUND TO BE A MAJOR BIOTRANSFORMATION OF ANETHOLE. METABOLISM VIA CINNAMOYL DERIV WAS MORE EXTENSIVE WITH THE PROPENYL SUBSTITUENT THAN FOR THE ALLYL COMPD; & FURTHER METABOLISM BY BETA-OXIDATION ALSO OCCURRED.

MeSH Pharmacological ClassificationSubstances added to foods and medicine to improve the taste.
Absorption, Distribution and Excretion · 5 件

/IN BIOTRANSFORMATION OF ANETHOLE/...ANISIC ACID...CONSTITUTED THE MAJOR URINARY METABOLITE. ...THERE WAS A QUANTITATIVE RECOVERY OF THE DOSE ADMIN.

TRANS-ANETHOLE WAS AMONG 4 FOOD ADDITIVES STUDIED & FOUND LARGELY ABSORBED FROM DIGESTIVE TRACT BY PASSIVE DIFFUSION. ABSORPTION KINETICS VARY PARTIALLY BY DIFFERENCES OF COMPD IN COEFFICIENTS OF LIPOSOLUBILITY.

...TRANS-ANETHOLE USED IN PREPN OF ANIS-FLAVORED ALCOHOLIC BEVERAGES WAS STUDIED IN THE RABBIT & RAT AFTER IV & ORAL ADMIN. IT WAS EXCRETED RAPIDLY FROM THE ANIMAL REGARDLESS OF /ROUTE/ OF ADMIN. AFTER IV INJECTION, IT WAS FOUND CONCENTRATED IN LIVER, LUNGS & BRAIN; AFTER ORAL ADMIN...MOST OF IT REMAINED IN STOMACH.

TRANS-ANETHOLE IS ONE OF THE COMPOUNDS LARGELY ABSORBED FROM THE DIGESTIVE TRACT BY MECHANISM OF PASSIVE DIFFUSION.

THE METABOLITES OF ANETHOLE IN RATS WERE IDENTIFIED AND DETERMINED. MOST OF THE URINARY METABOLITES WERE ALSO DETECTED IN THE BILE.

用途と製造

Uses · 6 件

Chief constituent of anise, star anise, and fennel oils; Used as a flavoring agent (foods, beverages, and drugs) and fragrance (soaps and dentifrices); [Merck Index] Used to make anisaldehyde, as a sensitizer in bleaching colors in photography, an embedding material in microscopy, and an insect attractant; [HSDB]

Photographic Processing [Category: Other]

関連反応

0 件
反応記録を作成

現在のフィルター条件では反応記録がありません。

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
104-46-1、4180-23-8、50770-19-9
PubChem CID
637563
DTXSID
DTXSID9020087
ChEMBL
CHEMBL452630
ChEBI
CHEBI:2716
UNII
Q3JEK5DO4K
EC Number
203-205-5、224-052-0、256-753-2
Nikkaji
J4.026F、J61.645A
Flavoring Agents
EU Flavoring substances
Viscosity2.45X10-3 Pa.s

物理化学的性質

融点
20 to · 20 to 21 °C (68 to 70 °F; 293 to 294 K)
沸点
234 °C · 234 °C (453 °F; 507 K) ; 81 °C (178 °F; 354 K) at 2 mmHg
比重(密度)
0.998 g/cm3 · 0.998 g/cm3
屈折率
20 · n20/D 1.561(lit.)
闪点
195 °F · 195 °F
貯蔵温度
2 · Sealed in dry,2-8°C
溶解性
30 mg/ml; · DMSO: 30 mg/ml; PBS (pH 7.2): 10 mg/ml
外見
Oil
色
Colorless to off-white
臭い (Odor)
100 %で。甘いアニス甘草薬用 · 100.00%で。甘いアニス甘草薬用
においのタイプ
甘草
水溶解度
148.2 mg/L · 148.2mg/L(25℃)
Henry's Law Constant
9.9 · 9.9×10-2 mol/(m3Pa) at 25℃, Roon et al. (2005)
安定性
安定。可燃性。強力な酸化剤とは相容れない。
化粧品成分の機能
香料変性剤
LogP
3.39 · 3.39
CAS データベース
104 · 104-46-1(CAS DataBase Reference)
NISTの化学物質情報
1 · Benzene, 1-methoxy-4-(1-propenyl)-(104-46-1)
EPAの化学物質情報
Anethole (104-46-1)

化学的性質

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.

· 1 件

A mutagen and tumorigen; Causes hepatitis, somnolence, and coma in high-dose feeding studies of rats; [RTECS] Fennel oil is toxic by ingestion--may cause vomiting, seizures, and pulmonary edema; [HSDB] Food handlers may develop contact dermatitis to anethole; [Kanerva, p. 1752] May cause irritation; [MSDSonline]

FDA Requirements · 2 件

Anethole used as a synthetic flavoring substance or adjuvant in food for human consumption is generally recognized as safe when used in accordance with good manufacturing practice.

Anethole used as a synthetic flavoring substance or adjuvant in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.

Reactive GroupEthers
FIFRA Requirements · 1 件

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. p-Anethole is found on List C. Case No: 3018; Pesticide type: Rodenticide; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Anethole; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Reactivity ProfileProtect from light (NTP, 1992).
Air and Water ReactionsSlightly water soluble (NTP, 1992).
Hazard Classes and Categories · 3 件

Skin Sens. 1B (95.3%)

Skin Sens. 1 (93.8%)

Skin sensitisation - category 1

安全と保護具

Fire FightingTo extinguish a fire involving this chemical you may use a dry chemical, carbon dioxide, foam or halon extinguisher; a water spray may also be used. (NTP, 1992)
First Aid · 1 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: Use absorbent paper to pick up spill material. Contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash contaminated surfaces with alcohol followed by washing with a strong soap and water solution.

Disposal Methods · 1 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Isolation and EvacuationExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Personal Protective Equipment (PPE)MINIMUM PROTECTIVE CLOTHING: When working with this chemical, you should wear impervious coveralls, shoe covers and gloves.

毒性情報

Body BurdenAnethole was discovered in one out of 46 samples of human adipose tissue (age class: 0-14 yrs and North Central region(1).
InteractionsMEAN SLEEPING TIME IN MICE TREATED WITH 50 MG/KG NA-PENTOBARBITAL ABOUT DOUBLED WITH 20 & 50 MG OF SOME COMPD; ANETHOLE WAS LESS ACTIVE.
Environmental Fate · 3 件

TERRESTRIAL FATE: Anethole will have a medium to low mobility(3) in soil based on estimated Koc values ranging from 327 to 680(1,2). Insufficient data are available to predict the relative importance or rate of biodegradation in soil conditions(SRC).

AQUATIC FATE: Volatilization of anethole from water is not rapid but could possibly be significant based upon estimated Henry's Law constant of 7.18X10-5 atm cu m/mol(1,2,SRC). Volatilization half-lives from a model river (1 m deep flowing 1 m/sec with a wind velocity of 3 m/sec) and a model lake (1 meter deep) can be estimated to be about 18 hours and 9 days respectively(2). Insufficient data are available to predict the relative importance or rate of biodegradation from natural waters(SRC). Aquatic bioconcentration is not expected to be an important fate process, however, based on a Koc value of 680(3), some absorption to sediment may occur(SRC).

ATMOSPHERIC FATE: Based on an extrapolated vapor pressure of approximately 0.005 mm Hg at 25 °C(1), anethole will exist in the atmosphere in the vapor phase(2). It will degrade in the atmosphere by reaction with photochemically produced hydroxyl radicals with estimated half-lives of 4.9 and 4.5 hrs for the cis and trans isomers, respectively(3). Anethole will also degrade in the atmosphere by reaction with atmospheric ozone with estimated half-lives of 4.03 and 2.02 hrs for the cis and trans isomers, respectively(3).

Food Survey ValuesAn analysis of chickpea seed, found a 0.9% constituent of anethole(1).
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Effluent Concentrations · 1 件

In a monitoring study of organic constituents of kraft mill aerated stabilization basins in Oregon, anethole was detected at trace quantities (detection limits were not reported)(1). Another study of kraft mill aerated lagoons also identified anethole in four samples of an unbleached kraft aerated lagoon influent and effluent in the following concentrations (ppb): 30-60, 20-10, 30-trace (detection limit not reported), and 20-10; influents and effluents respectively(2). A third study of unbleached treated kraft paper mill wastewater in Georgia found anethole at approximately 0.007 mg/l(3).

Soil Adsorption/Mobility · 1 件

Using a structure estimation method based on molecular connectivity indexes, the Koc for anethole can be estimated to be about 680(1). The Koc for anethole can be estimated to be about 327 based on an experimental water solubility of 111 mg/L(3) and a regression derived equation(2). According to a suggested classification scheme(4), these estimated Koc values suggest that anethole has medium to low soil mobility.

Natural Pollution SourcesAnethole occurs naturally in anise, star anise, and fennel oils(1) and chickpea seed(2).
Human Toxicity Excerpts · 4 件

A CASE OF STOMATITIS HAS BEEN REPORTED AFTER USE OF DENTURE CREAM CONTAINING OIL OF ANISE (80-90% ANETHOLE). APPLIED TO SKIN ANETHOLE CAUSES ERYTHEMA, SCALING & VESICULATION.

COMPARED WITH RESULTS OF TESTS WITH BALSAMS & OTHER ESSENTIAL OILS, STAR OF ANISE OIL DOES NOT GIVE CROSS-REACTION & PSEUDO CROSS-SENSITIVITY. PT POSITIVE TO THIS OIL ARE FREQUENTLY POSITIVE TO ANETHOLE.

ANETHOLE TESTED @ 2% IN PETROLATUM PRODUCED NO IRRITATION AFTER A 48-HR CLOSED PATCH TEST IN 25 HUMAN SUBJECTS. A MAXIMIZATION TEST WAS CARRIED OUT ON 25 VOLUNTEERS. MATERIAL WAS TESTED @ 2% CONCN IN PETROLATUM & PRODUCED NO REACTIONS.

ANETHOLE WAS THE MOST SENSITIZING OF APPROX 8 SENSITIZING COMPONENTS. SYNERGISM MAY HAVE BEEN INVOLVED IN THE IRRITATING & SENSITIZING PROPERTIES.

Artificial Pollution Sources · 1 件

Chloronitrobenzenes are produced by nitration of chlorobenzene. The crude chloronitrobenzene obtained from the nitration process contains about 34% o-chloronitrobenzene, 65% p-chloronitrobenzene, and 1% m-chloronitrobenzene. The isomers are separated by a combination of crystallization and distillation.

Drug Induced Liver Injury · 4 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Anethole

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Environmental Bioconcentration · 1 件

Based upon an experimental water solubility of 111 mg/l(1), the BCF of anethole can be estimated to be approximately 43.4 from a regression-derived equation(2). This estimated BCF value suggests that bioconcentration in aquatic organisms is not expected to be an important fate process(SRC).

法規制情報

FDA Requirements · 2 件

Anethole used as a synthetic flavoring substance or adjuvant in food for human consumption is generally recognized as safe when used in accordance with good manufacturing practice.

Anethole used as a synthetic flavoring substance or adjuvant in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.

FIFRA Requirements · 1 件

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. p-Anethole is found on List C. Case No: 3018; Pesticide type: Rodenticide; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Anethole; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

安全データ

F
8
wgk
2
tsca
TSCA listed
rtecs
BZ9275000
risk_code
43-36/37/38-20/21/22
消防法
危-4-3-III
hazard_code
Xi,Xn
safety_code
36/37-36-26
有毒物質データの
104-46-1(Hazardous Substances Data)
危険度評価(NFPA 704基準/消防庁データ)
人的[青]=0

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

MFR ANISALDEHYDE; IN PERFUMERY, SOAP & DENTIFRICES; SENSITIZER IN BLEACHING COLORS IN COLOR PHOTOGRAPHY; AS EMBEDDING MATERIAL IN MICROSCOPY; PHARMACEUTIC AID (FLAVOR); VET: HAS BEEN USED AS A CARMINATIVE & AS A FLAVORING AGENT

AS FLAVOR INGREDIENT

IN LICORICE CANDIES

U.S. Production · 3 件

2023: 2,063,610 lb

2023: 250,000 - <400,000 lb

(1991) 1,641,000 kg

Consumer UsesFragrance
Industry Uses · 2 件

Intermediate

Other

Methods of Manufacturing · 2 件

SYNTHESIS BY ESTERIFICATION OF P-CRESOL WITH METHYL ALCOHOL & SUBSEQUENT CONDENSATION WITH ACETALDEHYDE (PERKINS). ...MOST COMMON METHOD...FROM PINE OIL. BY FRACTIONAL DISTILLATION.../OF/ ESSENTIAL OILS OF ANISE, STAR ANISE & FENNEL. ...ANISE...CONTAIN...85% ANETHOLE; FENNEL FROM 60 TO 70%.

SEPN OF CIS & TRANS ISOMERS: NAVES ET AL, COMPT REND 246: 1734 (1958); BULL SOC CHIM FRANCE 1958, 566; HELY CHIM ACTA 43: 230 (1960); FERRONI ET AL, GAZZ CHIM ITAL 92: 1198 (1962). SYNTHESIS: MUELLER, ROSCHEISEN, BER 90: 543 (1957).

Formulations/PreparationsGRADES: USP (TECHNICAL); FCC (FOOD CHEMICALS CODEX).
Household Products · 3 件

Cosmetics product ingredient: 1-Methoxy-4-(1E)-1-propen-1-yl-benzene (trans-Anethole) (Anethole)

Information on 22 consumer products that contain Anethole in the following categories is provided:

Information on 45 consumer products that contain Trans-Anethole in the following categories is provided:

Use Classification · 6 件

Fragrance Ingredients

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 6 件

All Other Basic Organic Chemical Manufacturing

All Other Basic Organic Chemical Manufacturing

Benzene, 1-methoxy-4-(1-propen-1-yl)-: ACTIVE

Benzene, 1-methoxy-4-(1E)-1-propen-1-yl-: ACTIVE

Benzene, 1-methoxy-4-(propen-1-yl)-: INACTIVE

...THERE IS REGULAR USE OF COMPOUNDED ESSENTIAL OILS CONSISTING...OF...ANETHOL /IN MFR OF SWEET LIQUEURS/. ... THE EFFECTIVE YIELD OF ANETHOL, BASED ON THE FINISHED LIQUEUR "AS IS" IS APPROX 1:2000.

応用分野 · 5 件

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。

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.

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

一般的な説明White crystals or a liquid. Odor of anise oil and a sweet taste.

調製方法 · 1 件

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, 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.

上流・下流製品情報

上流原料

4-ブロモアニソールアニス種子油ナトリウムアニソールウイキョウ油1,4-ジメトキシベンゼン4-フェニル-1-ブテンp-アニスアルデヒドアリルブロミドプロピオン酸無水物水酸化ナトリウム4-アリルアニソールメチルエーテルアリルベンゼン3-メチルアクリル酸プロピオン酸 ナトリウム

下流製品

アネトールトリチオンtrans-アネトール1-プロピル-4-メトキシベンゼンp-アニスアルデヒドヘキセストロール4-Methoxy-beta-bromopropiophenone

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補足説明

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。

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