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멘틸 아세테이트

Menthyl acetate

HCID 27867
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
16409-45-3
표준 SMILES
CC(=O)OC1CC(C)CCC1C(C)C
InChIKey
XHXUANMFYXWVNG-UHFFFAOYSA-N
분자식
C12H22O2
평균 분자량
198.3 g/mol
단동위원소 질량
198.16197994

개요

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

이름 및 식별자

우선 이름
Menthyl acetate
IUPAC
(5-methyl-2-propan-2-ylcyclohexyl) acetate
현지명
멘틸 아세테이트
영어명
L-MENTHYL ACETATE
분자식
C12H22O2
분자량
198.3

이름 및 동의어

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
이름 더 보기
멘틸아세테이트L-멘틸아세테이트2-Isopropyl-5-methylcyclohexyl acetatel-Menthol acetateMENTHYL ACETATE (ISOMER UNSPECIFIED)FEMA 2668femanumber:2668mentholaceticesterMENTHYL ACETATE, L-(-)-ACETOXY-P-MENTHANEaceticacidmenthylester(R)-(-)-MENTHYL ACETATE
249-409-8LF3LEI45OH89-48-52623-23-6dl-Menthyl acetate29066-34-0(5-methyl-2-propan-2-ylcyclohexyl) acetate2230-87-7

데이터베이스 식별자

CAS
16409-45-3、2230-87-7、2552-91-2、2623-23-6、29066-34-0、89-48-5

물성

구조 계산 물성

XLogP
3.6
극성 표면적
26.3 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
3
무거운 원자 수
14
형식 전하
0
복잡도
198

실험 및 물리화학적 성질

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

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

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

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)

유해성 정보

Regulatory Information · 6건

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 · 3건

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]

화학 및 산업

약리 정보

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

용도 및 제조

Uses · 5건

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 · 4건

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:

관련 반응

1건
반응 기록 만들기
HRID 1794976 반응식
HRID 1794976생성물로uspto-grants-2006_04

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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
· 2건

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 · 2건

227 °C

227-228 °C

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

물리화학적 성질

녹는점
25 °C · <25 °C
끓는 점
229 · 229-230 °C(lit.)
밀도
0.92 g/mL · 0.92 g/mL at 25 °C(lit.)
FEMA
2668 · 2668 | MENTHYL ACETATE (ISOMER UNSPECIFIED)
굴절률
20 · n20/D 1.447(lit.)
인화점
171 °F · 171 °F
냄새
100 %에서 · 100.00%에서. 차 냉각 민트 과일 베리
냄새 유형
멘톨
생물학적 소스
synthetic
JECFA Number
431 · 431
Henry's Law Constant
1.2 · 1.2×10-2 mol/(m3Pa) at 25℃, HSDB (2015)
주요 응용
향료 및 향
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

화학적 성질

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 · 1건

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 · 5건

Aquatic Chronic 2 (> 99.9%)

Aquatic Chronic 2 (99.5%)

Aquatic Chronic 2 (100%)

Aquatic Chronic 2 (100%)

Aquatic Chronic 2 (100%)

안전 및 보호

Disposal Methods · 1건

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.

독성 정보

Environmental Fate · 3건

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 · 1건

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 · 1건

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 · 1건

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 · 1건

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 · 1건

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 · 1건

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)

규제 정보

FDA Requirements · 1건

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.

안전 데이터

wgk
3
rtecs
AI5900000
독성
rabbit,LD50,skin,> 5gm/kg (5000mg/kg),Food and Cosmetics Toxicology. Vol. 14, Pg. 479, 1976.
기존화학 물질
KE-23084
Hazard Classifications
Aquatic Chronic 2
스토리지 클래스
10 - Combustible liquids
유해 물질 데이터
16409-45-3(Hazardous Substances Data)
Use Classification · 6건

Fragrance Ingredients

Fragrance Ingredients

Fragrance Ingredients

Fragrance Ingredients

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 4건

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/

응용 분야

출처Reported 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.

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

제조 방법

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

공급사30 곳

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