Methyl Decanoate

HCID 8050CAS 110-42-9

Basic information

Standard SMILES
CCCCCCCCCC(=O)OC
InChIKey
YRHYCMZPEVDGFQ-UHFFFAOYSA-N
Molecular formula
C11H22O2
Average molar mass
186.29 g/mol
Monoisotopic mass
186.16197994

Overview

Methyl decanoate is a fatty acid methyl ester and a decanoate ester.

Names & identifiers

Preferred name
Methyl Decanoate
IUPAC
methyl decanoate
English name
Methyl decanoate
Molecular formula
C11H22O2
Molecular weight
186.29

Names & synonyms

METHYL DECANOATE110-42-9Methyl caprateDecanoic acid, methyl esterCapric acid methyl esterMethyl caprinateMethyl-n-caprateUniphat A30Metholene 2095Methyl decanoate (natural)CCRIS 673DTXSID4026842
Show more names
DECANOIC ACID METHYL ESTERMethyl GCuniphata30ESTASOL MD10metholene2095
formyl decanoateHSDB 5399n-Capric acid methyl esterNSC 3713EINECS 203-766-6UNII-U9L2W51J0BBRN 1759170AI3-26168

Database identifiers

CAS
110-42-9
PubChem CID
8050
DTXSID
DTXSID4026842
ChEMBL
CHEMBL2137647
ChEBI
CHEBI:143577
UNII
U9L2W51J0B
EC Number
203-766-6
Nikkaji
J1.975E

Properties

Computed structural properties

XLogP
4.7
Topological polar surface area
26.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
9
Heavy atoms
13

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Esters, Other
LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Short fatty esters [FA0710]
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Methyl decanoate) -> IFRA transparency List
Pesticides · 2 items

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Not approved

LogP · 2 items

log Kow= 4.41

4.41

Physicochemical properties

Melting point
-14 · -14--11 °C (lit.)
Boiling point
108 °C/10 · 108 °C/10 mmHg 224 °C (lit.)
Density
0.871 g/mL · 0.871 g/mL at 20 °C (lit.)
vapor pressure
4.93 Pa · 4.93Pa at 25℃
refractive index
20 · n20/D 1.425(lit.)
FLAVIS Number
9.251 · 09.251 | Methyl decanoate

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 44.7% (118 of 264) of reports.

H411 (53%): 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 264 reports by companies from 5 notifications to the ECHA C&L Inventory.

Warning

H227: Combustible liquid [Warning Flammable liquids]

Hazard information

Regulatory Information · 5 items

Chemical: Decanoic acid, methyl ester

Decanoic acid, methyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Decanoic acid, methyl ester 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)

2008/127, Reg. (EU) 2017/195, Reg. (EU) 2020/1160, Reg. (EU) 2021/745, Reg. (EU) 2023/1446, Reg. (EU) 2024/1280, Reg. (EU) No 540/2011

Status: Active Update: 06-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/16051

Decanoic acid, methyl ester: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Decanoic acid, methyl ester: Human health tier I assessment
Hazards SummaryFatty acid C6-C10 methylester: Irritating to rabbit and human skin and mildly irritating to rabbit eyes; [IUCLID]
Hazard Classes and Categories · 2 items

Aquatic Chronic 2 (53%)

Flammable liquids - Category 4

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

Body BurdenOne of eight samples of mother's milk collected in 4 urban/industrial areas in the United States were positive for the presence of methyl decanoate(1,2).
Interactions · 1 item

Linear saturated fatty acid methyl esters were comitogenic with lectins for mouse lymphocytes, the degree of comitogenicity being strongly dependent on the length of the acyl group, and maximal for methyl tetradecanoate. Lesser effects were found for analogs with 10, 12, or 16 acyl carbon atoms, whereas those with fewer than 10 or more than 16 were inactive. /Methyl esters/

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 470(SRC), determined from a structure estimation method(2), indicates that methyl decanoate is expected to be moderately mobile in soil(SRC). Volatilization of methyl decanoate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.0017 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Methyl decanoate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.037 mm Hg(4). Methyl decanoate is expected to rapidly biodegrade in aerobic soils as suggested by the rapid biodegradation of structurally similar long-chain fatty acid esters(5-7).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 470(SRC), determined from a structure estimation method(2), indicates that methyl decanoate is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 0.0017 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Volatilization half-lives for a model river and model lake are 5 hours and 6 days, respectively(SRC), using an estimation method(3). According to a classification scheme(5), an estimated BCF of 50(SRC) from its log Kow of 4.41(11) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate. Methyl decanoate is expected to rapidly biodegrade in aerobic waters as suggested by the rapid biodegradation of structurally similar long-chain fatty acid esters(7-9). An estimated base-catalyzed second-order hydrolysis rate constant of 0.030 L/mole-sec(10,SRC) corresponds to half-lives of 7 years and 270 days at pH values of 7 and 8, respectively(10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl decanoate, which has a vapor pressure of 0.037 mm Hg at 25 °C(2), will exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl decanoate 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 37 hours(SRC) from its estimated rate constant of 1.0X10-11 cu cm/molecule-sec at 25 °C(3).

Food Survey ValuesMethyl decanoate was identified as a component of the aroma fraction of blue cheese(1) and Beaufort cheese(2). It was detected as a natural flavoring constituent of cassava and farine(3).
Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for methyl decanoate can be estimated to be about 470(SRC). According to a classification scheme(2), this estimated Koc value suggests that methyl decanoate is expected to have moderate mobility in soil.

Natural Pollution SourcesMethyl decanoate was identified as a component of cassava and farine(1) and blue(2) and Beaufort cheese(3).

Safety data

PPE
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
rtecs
HD9830000
ridadr
UN 3082 9 / PGIII
hs_code
29159000

Chemistry & industry

Pharmacology

Cellular LocationsExtracellular

Uses & manufacturing

Uses · 6 items

Found in cassava, farine, and blue and Beaufort cheeses; Used as flavoring agent, insect attractant, pesticide stabilizer, and plant growth regulator; Also used to make caproic acid, detergents, emulsifiers, wetting agents, stabilizers, resins, lubricants, plasticizers, alkanolamides, and fatty alcohols and acids; [HSDB]

Farming (Pesticides) [Category: Industry]

AS WINE BOUQUET; COGNAC ESSENCE; INSECT ATTRACTANT; BOTH IN AND AS STABILIZER OF PESTICIDE FORMULATIONS

PLANT GROWTH REGULATOR

Int for caproic acid, detergents, emulsifiers, wetting agents, stabilizers, resins, lubricants, plasticizers, flavoring

CHEM INT-EG, FOR ALKANOLAMIDES, FATTY ALCOHOLS & ACIDS

U.S. Production2023: 1,000,000 - <5,000,000 lb
Industry UsesIntermediate
Methods of Manufacturing · 2 items

Esterification of capric acid with methanol or alcoholysis of coconut oil, purified by fractional vacuum distillation.

REACTION OF TRIGLYCERIDES, EG, COCONUT OR PALM KERNEL OIL, WITH METHANOL FOLLOWED BY FRACTIONAL DISTILLATION; REACTION OF CAPRIC ACID WITH METHANOL

Formulations/PreparationsGrades: ...99.8% Pure.
Use ClassificationFragrance Ingredients
Applications · 2 items

UsesMethyl decanoate is employed as an intermediate for caproic acid, detergents, emulsifiers, wetting agents, stabilizers, resins, lubricants, plasticizers and flavouring. As a chemical intermediate for alkanolamides, fatty alcohols, and acids.

General DescriptionMethyl decanoate is reported to occur in parmesan cheese, sparkling wine and banana.

Preparation methods

PreparationMethyl decanoate is prepared by esterification of capric acid with methanol or alcoholysis of coconut oil, purified by fractional vacuum distillation.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海比阳实业有限公司+86-21-52699951; +8613917686115 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]

Additional notes

DefinitionChEBI: Methyl decanoate is a fatty acid methyl ester and a decanoate ester. It is a metabolite found in or produced by Saccharomyces cerevisiae.

Related reactions

14 records

Linked notes

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