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
Show more names
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
- Formal charge
- 0
- Complexity
- 121
Experimental & physicochemical properties
Pesticides
Agrochemicals -> Pesticide active substances
Active substance -> EU Pesticides database: Not approved
LogP
log Kow= 4.41
4.41
Solubility
Insol in water; very sol in ethyl alc, ether; slightly sol in chloroform, carbon tetrachloride
0.0044 mg/mL at 20 °C
Boiling Point
224 °C @ 760 mm Hg
108.00 °C. @ 10.00 mm Hg
Melting Point
-18 °C
-18 °C
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
- Flash point
- 202 °F · 202 °F
- storage temp.
- room temp
- solubility
- 100 mg/mL, · chloroform: soluble100mg/mL, clear
- form
- Liquid
- color
- Clear colorless
- Odor
- 100 % · at 100.00 %. oily wine fruity floral
- Odor Type
- fermented
- biological source
- synthetic
- Viscosity
- 2.4 mm2/s · 2.4mm2/s
- explosive limit
- 0.7 % · 0.7%(V)
- Water Solubility
- Soluble in alcohol. Insoluble in water.
- BRN
- 1759170 · 1759170
- Henry's Law Constant
- 1.1 · 1.1×10-2 mol/(m3Pa) at 25℃, Aprea et al. (2007)
- Dielectric constant
- 3.86 · 3.8599999999999999
- Major Application
- cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care
- InChI
- 1S/C11H22O2/c1-3-4-5-6-7-8-9-10-11(12)13-2/h3-10H2,1-2H3
- InChIKey
- YRHYCMZPEVDGFQ-UHFFFAOYSA-N
- SMILES
- CCCCCCCCCC(=O)OC
- LogP
- 4.42 at · 4.42 at 36℃
- CAS DataBase Reference
- 110 · 110-42-9(CAS DataBase Reference)
- FDA UNII
- 9 L2W51J0B · U9L2W51J0B
- NIST Chemistry Reference
- Decanoic acid, methyl ester(110-42-9)
- EPA Substance Registry System
- Methyl decanoate (110-42-9)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 9 · GHS09
- Signal word
- Warning
- Hazard statements
- 410 · H410
- Precautionary statements
- 273 · P273-P391-P501
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- Safety Statements
- 24 · 24/25
- RIDADR
- 3082 · UN 3082 9 / PGIII
- WGK Germany
- 1 · 1
- RTECS
- 9830000 · HD9830000
- TSCA
- TSCA listed
- HazardClass
- 9 · 9
- HS Code
- 29159000 · 29159000
- Storage Class
- 10 · 10 - Combustible liquids
- Hazard Classifications
- 1 Aquatic · Aquatic Acute 1Aquatic Chronic 2
- Hazardous Substances Data
- 110 · 110-42-9(Hazardous Substances Data)
- REACH Registrations
- Active
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
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
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
Hazard Classes and Categories
Aquatic Chronic 2 (53%)
Flammable liquids - Category 4
Safety & protection
Disposal Methods
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
Interactions
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
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).
Soil Adsorption/Mobility
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.
Environmental Bioconcentration
An estimated BCF of 50 was calculated for methyl decanoate(SRC) using a log Kow of 4.41(1) and a regression-derived equation(2). According to a classification scheme(3), the estimated BCF suggests the potential for bioconcentration in aquatic organisms is moderate. However, bioconcentration studies on compounds which are structurally similar(4,5) suggest that bioconcentration may be lower than that indicated by the regression-derived equation due to the ability of aquatic organisms to readily metabolize this class of compounds.
Volatilization from Water/Soil
The Henry's Law constant for methyl decanoate is estimated as 0.0017 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that methyl decanoate is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as approximately 5 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as approximately 6 days(SRC). Methyl decanoate's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur but may be attenuated by adsorption to soil(SRC). Methyl decanoate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.037 mm Hg(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
- Signal word
- Warning
- Symbol(GHS)
- GHS09
- safety_code
- 24/25
- hazard_class
- 9
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H410
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 2
- Precautionary statements
- P273-P391-P501
- Hazardous Substances Data
- 110-42-9(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Uses & manufacturing
Uses
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
Methods of Manufacturing
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
General Manufacturing Information
Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing
Decanoic acid, methyl ester: ACTIVE
.../METHYL CAPRATE/ HAS BACTERICIDAL PROPERTIES.
An emulsion of this ester will debud chrysanthemums chemically. Not commercial.
Applications
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
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
Linked notes
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