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5-メチル-2-(1-メチルエチル)シクロヘキサノールアセタート

Menthyl acetate

HCID 27867
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
16409-45-3
標準SMILES
CC(=O)OC1CC(C)CCC1C(C)C
InChIKey
XHXUANMFYXWVNG-UHFFFAOYSA-N
分子式
C12H22O2
平均分子量
198.3 g/mol
単同位体質量
198.16197994

概要

(+/-)-Menthyl acetate is a p-menthane monoterpenoid.

名称と識別子

優先名称
Menthyl acetate
IUPAC
(5-methyl-2-propan-2-ylcyclohexyl) acetate
現地名
5-メチル-2-(1-メチルエチル)シクロヘキサノールアセタート
英語名
L-MENTHYL ACETATE
分子式
C12H22O2
分子量
198.3

名称と別名

Menthyl acetate16409-45-3Menthol, acetateMenthyl acetate racemicCyclohexanol, 5-methyl-2-(1-methylethyl)-, acetateAcetic acid, p-menth-3-yl ester, dl-DTXSID20859153RefChem:1088940DTXCID30210413Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1alpha,2beta,5alpha)-201-911-8240-459-6
名称をさらに表示
酢酸p-メンタン-3-イル2-イソプロピル-5-メチル-1-シクロヘキサノールアセタート酢酸2-イソプロピル-5-メチルシクロヘキシルメンチルアセタート酢酸5-メチル-2-(1-メチルエチル)シクロヘキシル2-イソプロピル-5-メチルシクロヘキサノールアセタートメントールアセタート3-アセトキシ-p-メンタンp-メンタン-3-オールアセタート酢酸メンチル5-メチル-2-(1-メチルエチル)シクロヘキサノールアセタート2-イソプロピル-5-メチルシクロヘキシル=アセタート5-メチル-2-(プロパン-2-イル)シクロヘキシル アセタート2-Isopropyl-5-methylcyclohexyl acetatel-Menthol acetateMENTHYL ACETATE (ISOMER UNSPECIFIED)FEMA 2668femanumber:2668mentholaceticester

物性

構造計算による物性

XLogP
3.6
極性表面積
26.3 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
3
重原子数
14
形式電荷
0
複雑度
198

実験および物理化学的性質

Chemical ClassesBiological Agents -> Plant Oils and Extracts
CosmeticsMasking; Refreshing
SpringerMaterials PropertiesBoiling point
Fragrances · 5 件

Fragrance Ingredient (Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, (1a,2a,5b)-) -> IFRA transparency List

Fragrance Ingredient (dl-Menthyl acetate) -> IFRA transparency List

Fragrance Ingredient (l-Menthyl acetate (1alpha,2beta,5alpha)) -> IFRA transparency List

Fragrance Ingredient (Menthyl acetate (1alpha,2beta,5alpha)) -> IFRA transparency List

Fragrance Ingredient (Menthyl acetate (isomer unspecified)) -> IFRA transparency List

OdorEARTHY, WEEDY, FRUITY, BERRY-LIKE ODOR
TasteEARTHY, WEEDY, FRUITY, BERRY-LIKE TASTE
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Densitydl-, (-)- 0.919-0.924
Flavoring AgentsEU Flavoring substances
Solubility · 2 件

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1657) of reports.

H411 (> 99.9%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P273, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1657 reports by companies from 5 notifications to the ECHA C&L Inventory.

H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P273, P391, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 6 件

Chemical: Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 1-acetate, (1R,2S,5R)-rel-

Chemical: Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, [1R-(1.alpha.,2.beta.,5.alpha.)]-

Chemical: Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate

Regulation (EC) No 1831/2003 (amended)

Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 1-acetate, (1R,2S,5R)-rel- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 1-acetate, (1R,2S,5R)-rel- 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)

REACH registered substance: Menthyl acetate (EC: 201-911-8)

Other Safety Information · 3 件

IMAP assessments - Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate, [1R-(1.alpha.,2.beta.,5.alpha.)]-: Human health tier I assessment

IMAP assessments - Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate: Human health tier I assessment

IMAP assessments - Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 1-acetate, (1R,2S,5R)-rel-: Human health tier I assessment

Hazards SummaryEmergency treatment: Peppermint oil; [HSDB] Mild skin irritant in rabbits; [RTECS] Peppermint oil causes CNS depression and hypothermia in rat feeding studies; [Haddad, p. 1439]

化学と産業

薬理情報

Metabolism/MetabolitesAS AN ESTER IT IS PRESUMABLY HYDROLYZED IN THE ALIMENTARY TRACT TO MENTHOL AND ACETIC ACID.

用途と製造

Uses · 5 件

Found in peppermint oil; Used in perfumes and flavors; [Hawley] Peppermint oil contains menthol, menthone, and more than 30 other chemicals. It is widely used as a flavoring agent and herbal remedy. [Haddad, p. 1439]

In perfumery; emphasizes floral notes, especially that of rose, used in toilet waters having a lavender odor. Has been suggested for flavoring extracts having caraway or mint flavors.

USED IN COSMETICS /L-FORM/

USEFUL IN MINT FLAVORS, FRUIT FLAVORS, BERRY.

SUGGESTED FOR FLAVORING EXTRACTS HAVING CARAWAY OR MINT FLAVORS

U.S. Production2023: 10,342 lb
Consumer UsesFragrance
Industry UsesFragrance
Methods of ManufacturingBY REACTING ACETIC ANHYDRIDE WITH MENTHOL IN THE PRESENCE OF ANHYDROUS SODIUM ACETATE. NATURAL OCCURRENCE: ...A NORMAL CONSTITUENT OF PEPPERMINT OIL IN VARYING AMOUNTS, DEPENDING ON THE SOURCE. /L-ISOMER/
Formulations/PreparationsGRADE: 95% MIN. /L-ISOMER/
Household Products · 4 件

Information on 6 consumer products that contain Menthyl Acetate in the following categories is provided:

Information on 1 consumer products that contain L-Menthyl Acetate in the following categories is provided:

Information on 6 consumer products that contain Menthyl acetate in the following categories is provided:

Information on 1 consumer products that contain Dl-Menthyl Acetate in the following categories is provided:

Use Classification

関連反応

1 件
反応記録を作成
HRID 1794976 の反応式
HRID 1794976生成物としてuspto-grants-2006_04

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
MENTHYL ACETATE, L-
(-)-ACETOXY-P-MENTHANE
aceticacidmenthylester
(R)-(-)-MENTHYL ACETATE
249-409-8LF3LEI45OH89-48-52623-23-6dl-Menthyl acetate29066-34-0(5-methyl-2-propan-2-ylcyclohexyl) acetate2230-87-7

データベース識別子

CAS
16409-45-3、2230-87-7、2552-91-2、2623-23-6、29066-34-0、89-48-5
PubChem CID
27867
DTXSID
DTXSID20859153
ChEMBL
CHEMBL254585
ChEBI
CHEBI:191550
EC Number
201-911-8、218-767-7、220-076-0、240-459-6、249-409-8
Nikkaji
J156.147B

soluble in alcohol, propylene glycol, most fixed oils; slightly soluble in water, glycerol

1 ml in 6 ml 70% alcohol; 1 ml in 1 ml 80% alcohol (in ethanol)

Boiling Point · 2 件

227 °C

227-228 °C

DecompositionWhen heated to decomposition it emits acrid smoke and irritating vaors.

物理化学的性質

融点
25 °C · <25 °C
沸点
229 · 229-230 °C(lit.)
比重(密度)
0.92 g/mL · 0.92 g/mL at 25 °C(lit.)
FEMA
2668 · 2668 | MENTHYL ACETATE (ISOMER UNSPECIFIED)
屈折率
20 · n20/D 1.447(lit.)
闪点
171 °F · 171 °F
臭い (Odor)
100 %で。ティークーリングミントフルーティーベリー · 100.00%で。ティークーリングミントフルーティーベリー
においのタイプ
メンソリック
由来生物
synthetic
JECFA Number
431 · 431
Henry's Law Constant
1.2 · 1.2×10-2 mol/(m3Pa) at 25℃, HSDB (2015)
主な用途
フレーバーそして香料
InChI
1S/C12H22O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h8-9,11-12H,5-7H2,1-4H3
InChIKey
XHXUANMFYXWVNG-UHFFFAOYSA-N
SMILES
CC(C)C1CCC(C)CC1OC(C)=O
LogP
4.1 · 4.10
CAS データベース
16409 · 16409-45-3(CAS DataBase Reference)

化学的性質

化学的特性l-Menthyl acetate has a fresh odor similar to mint and rose (on dilution). It has a characteristic, fresh, pungent flavor, different from menthol (being much milder). It has a cool mouthfeel with only a trace of mint flavor.

FDA Requirements · 1 件

Menthyl acetate is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient. Isobutyl acetate synthetic flavoring substances & adjuvants may be safely used in food in accordance with the following conditions ... They consist of one or more of the following /substances including isobutyl acetate/ used alone or in combination with flavoring substances generally recognized as safe in food, or regulated by an appropriate section in this part.

Hazard Classes and Categories · 5 件

Aquatic Chronic 2 (> 99.9%)

Aquatic Chronic 2 (99.5%)

Aquatic Chronic 2 (100%)

Aquatic Chronic 2 (100%)

Aquatic Chronic 2 (100%)

安全と保護具

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.

毒性情報

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5800(SRC), determined from an estimated log Kow of 4.39(2,SRC) and a regression-derived equation(3), indicates that menthyl acetate is expected to be immobile in soil(SRC). Volatilization of menthyl acetate from moist soil surfaces is expected to occur(SRC) given an estimated Henry's Law constant of 8.3X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, volatilization from moist soil surfaces is expected to be attenuated by adsorption to organic matter(SRC). In general, acetates are expected to be readily biodegradable(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5800(SRC), determined from an estimated log Kow of 4.39(2,SRC) and a regression-derived equation(3), indicates that menthyl acetate is expected to adsorb to suspended solids and sediment in water(SRC). Menthyl acetate is expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 8.3X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated volatilization half-lives for a model river and model lake are 5.6 hours and 6.0 days, respectively(3,SRC). However, adsorption to suspended solids and sediment in the water column is expected to attenuate this process(SRC). The volatilization half-life from a model pond 2 m deep is estimated to be about 2.7 days ignoring adsorption(5); when considering maximum adsorption, the volatilization half-life increases to 94 days(5). According to a classification scheme(6), an estimated BCF of 1300(3,SRC), from an estimated log Kow(2,SRC), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). In general, acetates are expected to be readily biodegradable(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), menthyl acetate, which has a vapor pressure of 0.10 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase menthyl acetate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 21 hours(3,SRC).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Soil Adsorption/Mobility · 1 件

The Koc of menthyl acetate is estimated as approximately 5800(SRC), using an estimated log Kow of 4.39(1,SRC) and a regression-derived equation(2,SRC). According to a classification scheme(3), this estimated Koc value suggests that menthyl acetate is expected to be immobile in soil(SRC).

Natural Pollution SourcesMenthyl acetate is present in peppermint oil(1).
Artificial Pollution SourcesMenthyl acetate's production and use in perfumery(1) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1 件

An estimated BCF of 1300 was calculated for menthyl acetate(SRC), using an estimated log Kow of 4.39(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC).

Volatilization from Water/Soil · 1 件

The Henry's Law constant for menthyl acetate is estimated as 8.3X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that menthyl acetate is expected to volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the estimated volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is approximately 5.6 hours(2,SRC). The estimated volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is approximately 6.0 days(2,SRC). The volatilization half-life from a model pond 2 m deep is estimated to be about 2.7 days ignoring adsorption(3); when considering maximum adsorption, the volatilization half-life increases to 94 days(3). Menthyl acetate's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces may occur(SRC).

Environmental Abiotic Degradation · 1 件

The rate constant for the vapor-phase reaction of menthyl acetate with photochemically-produced hydroxyl radicals has been estimated as 1.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 21 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). A base-catalyzed second-order hydrolysis rate constant of 3.0X10-2 L/mol-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 7.3 years and 270 days at pH values of 7 and 8, respectively(2,SRC).

Probable Routes of Human Exposure · 1 件

Occupational exposure to menthyl acetate may occur through inhalation and dermal contact with this compound at workplaces where menthyl acetate is produced or used. The general population may be exposed to menthyl acetate via inhalation and dermal contact with consumer products, such as perfumes, containing menthyl acetate, and via ingestion of food. (SRC)

Environmental Water ConcentrationsDRINKING WATER: Menthyl acetate was qualitatively detected in drinking water in Seattle, WA in 1976(1).
Environmental Fate/Exposure Summary · 1 件

Menthyl acetate is present in peppermint oil. Menthyl acetate's production and use in perfumery may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 0.10 mm Hg at 25 °C indicates menthyl acetate will exist solely as a vapor in the ambient atmosphere. Vapor-phase menthyl acetate will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 21 hours. If released to soil, menthyl acetate is expected to have no mobility based upon an estimated Koc of 5800. Volatilization from moist soil surfaces may occur based upon an estimated Henry's Law constant of 8.3X10-4 atm-cu m/mole. However, adsorption to organic matter is expected to attenuate this process. If released into water, menthyl acetate is expected to adsorb to suspended solids and sediment in water based on the estimated Koc. Volatilization from water surfaces may be an important fate process based on the estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 5.6 hours and 6.0 days, respectively. However, adsorption to suspended solids and sediment in the water column is expected to attenuate this process. An estimated BCF of 1300 suggests the potential for bioconcentration in aquatic organisms is very high. Estimated hydrolysis half-lives of 270 days and 7.3 years at pH values of 8 and 7, respectively, suggest hydrolysis is not expected to be an important process. In general, acetates are expected to be readily biodegradable. Occupational exposure to menthyl acetate may occur through inhalation and dermal contact with this compound at workplaces where menthyl acetate is produced or used. The general population may be exposed to menthyl acetate via inhalation and dermal contact with consumer products, such as perfumes, containing this compound, and via ingestion of food. (SRC)

法規制情報

FDA Requirements · 1 件

Menthyl acetate is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient. Isobutyl acetate synthetic flavoring substances & adjuvants may be safely used in food in accordance with the following conditions ... They consist of one or more of the following /substances including isobutyl acetate/ used alone or in combination with flavoring substances generally recognized as safe in food, or regulated by an appropriate section in this part.

安全データ

wgk
3
rtecs
AI5900000
毒性
rabbit,LD50,skin,> 5gm/kg (5000mg/kg),Food and Cosmetics Toxicology. Vol. 14, Pg. 479, 1976.
Hazard Classifications
Aquatic Chronic 2
ストレージクラス
10 - Combustible liquids
有毒物質データの
16409-45-3(Hazardous Substances Data)
· 6 件

Fragrance Ingredients

Fragrance Ingredients

Fragrance Ingredients

Fragrance Ingredients

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 4 件

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 1-acetate, (1R,2S,5R)-rel-: ACTIVE

Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 1-acetate, (1R,2S,5R)-: ACTIVE

FEMA NUMBER: 2668; REPORTED USES: NON-ALCOHOLIC BEVERAGES 5.5 PPM; ICE CREAM, ICES 4.0 PPM; CANDY 26 PPM; BAKED GOODS 24 PPM; CHEWING GUM 5.2 PPM. /L-ISOMER/

応用分野 · 3 件

用途食品: 天然には西洋ハッカや和種ハッカなどの精油に含まれ、清涼感のある香気を有することから、人工ペパーミントや人工ハッカ油の着香目的で用いられています。

天然物の起源Reported as a normal constituent of peppermint oil in varying amounts, depending on the source; the synthetic product is optically levorotatory; the commercial product is optically inactive.

使用L-Menthyl Acetate is a component of essential oils extracted from natural sources.

調製方法

製造方法By reacting acetic anhydride with menthol in the presence of anhydrous sodium acetate.

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補足説明

定義本品は、酢酸とメントールのエステルであり、次の化学式で表される。