HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
Huagongshe Open Program:[email protected]AI access: llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.7.8
  1. Home
  2. /Compound

Menthyl acetate

HCID 27867
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
16409-45-3
Standard SMILES
CC(=O)OC1CC(C)CCC1C(C)C
InChIKey
XHXUANMFYXWVNG-UHFFFAOYSA-N
Molecular formula
C12H22O2
Average molar mass
198.3 g/mol
Monoisotopic mass
198.16197994

Overview

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

Names & identifiers

Preferred name
Menthyl acetate
IUPAC
(5-methyl-2-propan-2-ylcyclohexyl) acetate
English name
L-MENTHYL ACETATE
Molecular formula
C12H22O2
Molecular weight
198.3

Names & synonyms

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
Show more names
2-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

Database identifiers

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

Properties

Computed structural properties

XLogP
3.6
Topological polar surface area
26.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
3
Heavy atoms
14
Formal charge
0
Complexity
198

Experimental & physicochemical properties

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

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

Safety & regulation

GHS classification

GHS Classification · 6 items

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)

Hazard information

Regulatory Information · 6 items

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 items

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]

Chemistry & industry

Pharmacology

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

Uses & manufacturing

Uses · 5 items

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 items

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:

Related reactions

1 records
New reaction record
HRID 1794976 reaction equation
HRID 1794976As productuspto-grants-2006_04

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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
Flavoring Agents
EU Flavoring substances
Solubility · 2 items

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 items

227 °C

227-228 °C

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

Physicochemical properties

Melting point
25 °C · <25 °C
Boiling point
229 · 229-230 °C(lit.)
Density
0.92 g/mL · 0.92 g/mL at 25 °C(lit.)
FEMA
2668 · 2668 | MENTHYL ACETATE (ISOMER UNSPECIFIED)
refractive index
20 · n20/D 1.447(lit.)
FLAVIS Number
9.016 · 09.016 | Menthyl acetate
Flash point
171 °F · 171 °F
Odor
100 % · at 100.00 %. tea cooling minty fruity berry
Odor Type
mentholic
biological source
synthetic
JECFA Number
431 · 431
Henry's Law Constant
1.2 · 1.2×10-2 mol/(m3Pa) at 25℃, HSDB (2015)
Major Application
flavors and fragrances
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 DataBase Reference
16409 · 16409-45-3(CAS DataBase Reference)
UNSPSC Code
12164502 · 12164502
NACRES
21 · NA.21
Symbol(GHS)
9 · GHS09
Hazard statements
411 · H411
Precautionary statements
273 · P273
WGK Germany
3 · 3
RTECS
5900000 · AI5900000
Storage Class
10 · 10 - Combustible liquids
Hazard Classifications
2 · Aquatic Chronic 2
Hazardous Substances Data
16409 · 16409-45-3(Hazardous Substances Data)
Toxicity
50 · rabbit,LD50,skin,> 5gm/kg (5000mg/kg),Food and Cosmetics Toxicology. Vol. 14, Pg. 479, 1976.
FDA Requirements · 1 item

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 items

Aquatic Chronic 2 (> 99.9%)

Aquatic Chronic 2 (99.5%)

Aquatic Chronic 2 (100%)

Aquatic Chronic 2 (100%)

Aquatic Chronic 2 (100%)

Safety & protection

Disposal Methods · 1 item

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.

Toxicology

Environmental Fate · 3 items

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 item

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 item

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 item

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 item

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 item

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 item

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)

Regulatory information

FDA Requirements · 1 item

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.

Safety data

wgk
3
rtecs
AI5900000
Toxicity
rabbit,LD50,skin,> 5gm/kg (5000mg/kg),Food and Cosmetics Toxicology. Vol. 14, Pg. 479, 1976.
Symbol(GHS)
GHS09
Storage Class
10 - Combustible liquids
Hazard statements
H411
Hazard Classifications
Aquatic Chronic 2
Precautionary statements
P273
Hazardous Substances Data
16409-45-3(Hazardous Substances Data)
Use Classification · 6 items

Fragrance Ingredients

Fragrance Ingredients

Fragrance Ingredients

Fragrance Ingredients

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 4 items

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/

Applications · 3 items

OccurrenceReported 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.

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

UsesPerfumery, flavoring.

Preparation methods

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

Suppliers30 total

湖北成丰化工有限公司13125175253 · [email protected]
广州佳途科技股份有限公司81960175 18933936954 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]
陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]
Syntechem Co.,Ltd[email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
JINING XINHE CHEMICAL CO., LTD+8615318402391 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
Henan Alfa Chemical Co., Ltd+8618339805032 · [email protected]
湖北恒绿源科技有限公司027-88188016 18717196322 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
BOC Sciences[email protected]
成都康巴斯生物科技有限公司18582381569 · [email protected]
珠海奥博凯生物医药技术有限公司400-0628126 · [email protected]
Shaanxi Dideu New Materials Co. Ltd18192503167 · [email protected]
常州阿桑奇科技有限公司18961267976 · [email protected]
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
河南威梯希化工科技有限公司0371-53732842 13383863444 · [email protected]
厦门盈融达化工有限公司+86-0592-6210733 · [email protected]
career henan chemical co+86-0371-86658258 · [email protected]
成都圣美凯生物科技有限公司028-85157043 15882256948 · [email protected]
天津丹骏国际贸易有限公司15822601686 · [email protected]
LYSCHEM International LLC13911018262 · [email protected]
重庆卡兰医药有限公司[email protected]
Hebei Chuanghai Biotechnology Co., Ltd+86-15350571055 · [email protected]
郑州研德生物科技有限公司13298105281 · [email protected]
江苏博思特化工科技有限公司87161895 15651337098 · [email protected]
Hefei TNJ Chemical Industry Co.,Ltd.+86-0551-65418671 +86-189 4982 3763 · [email protected]
杭州药睿易成生物医药有限公司18072846723 · [email protected]
深圳利斯康医药科技有限公司+86-0755-89396905 +86-18025329037 · [email protected]

Additional notes

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