Methylmyristat

Methyl Myristate

HCID 31284CAS 124-10-7

Grundinformationen

Standard-SMILES
CCCCCCCCCCCCCC(=O)OC
InChIKey
ZAZKJZBWRNNLDS-UHFFFAOYSA-N
Summenformel
C15H30O2
Durchschnittliche Molmasse
242,4 g/mol
Monoisotopische Masse
242,2245802

Überblick

Methyl tetradecanoate is a fatty acid methyl ester resulting from the formal condensation of the carboxy group of tetradecanoic acid (myristic acid) with methanol. It has a role as a flavouring agent, a fragrance and a plant metabolite. It is functionally related to a tetradecanoic acid.

Namen und Bezeichner

Bevorzugter Name
Methyl Myristate
IUPAC
methyl tetradecanoate
Lokaler Name
Methylmyristat
Englischer Name
METHYL MYRISTATE
Summenformel
C15H30O2
Molmasse
242.4

Namen und Synonyme

Methyl tetradecanoateMETHYL MYRISTATE124-10-7Tetradecanoic acid, methyl esterUniphat A50Metholeneat 2495Methyl n-tetradecanoateMyristic acid, methyl esterFEMA No. 2722Tetradecanoic Acid Methyl EsterDTXSID5027019formyl tetradecanoate
Weitere Namen anzeigen
FEMA 2722TetradecanoicMyristic acid methylMethyl tetradecanoatMyristicin acid methylesterNSC 5029Emery 2214
NSC-5029RG9851783CDTXCID607019CHEBI:89199RefChem:158031C14-MES204-680-1Myristic acid methyl ester

Datenbank-Bezeichner

CAS
124-10-7
PubChem CID
31284
DTXSID
DTXSID5027019
ChEMBL
CHEMBL207549
ChEBI
CHEBI:89199
UNII
RG9851783C
EC Number
204-680-1
Nikkaji
J382D

Eigenschaften

Berechnete Struktureigenschaften

XLogP
6,8
Polarare Oberfläche (TPSA)
26,3 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
13
Schwere Atome
17

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Uses -> Emulsifiers/Surfactants
LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Short fatty esters [FA0710]
Cosmetics · 2 Einträge

Cosmetic ingredients (Methyl Myristate) -> CIR (Cosmetic Ingredient Review)

Emollient; Skin conditioning

SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Methyl myristate) -> IFRA transparency List
LogP · 3 Einträge

log Kow= 6.41

6.41

6.41

Physikochemische Eigenschaften

Schmelzpunkt
18 °C · 18 °C(lit.)
Siedepunkt
323 °C · 323 °C(lit.)
Dichte
0.855 g/mL · 0.855 g/mL at 25 °C(lit.)
Dampfdruck
0.065 Pa · 0.065 Pa (25 °C)
FEMA
2722 · 2722 | METHYL MYRISTATE
Brechungsindex
20 · n20/D 1.436(lit.)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 3 Einträge

This chemical does not meet GHS hazard criteria for 99.9% (1614 of 1616) of all reports.

Not Classified

Aggregated GHS information provided per 1616 reports by companies from 3 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: Tetradecanoic acid, methyl ester

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

Status: Active Update: 30-01-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/21958

Methyl myristate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Tetradecanoic acid, methyl ester: Human health tier I assessment
Hazards SummaryMay cause irritation; [MSDSonline]
FDA Requirements · 1 Eintrag

Methyl myristate is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

EPA Safer ChemicalChemical: Methyl myristate
Hazard Classes and CategoriesNot Classified

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

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.

Toxikologische Informationen

Body BurdenMethyl myristate was detected in thrombogenic coronary plaques in 1 of 2 human aortas samples at 10 ppb(1).
Interactions · 2 Einträge

LINEAR ALKANES OF SPECIFIC CHAIN LENGTH ENHANCED DIFFERENTIALLY THE MITOGENIC RESPONSE OF MURINE SPLEEN LYMPHOCYTES TO THE LECTIN PHYTOHEMAGGLUTININ. WITHIN THE HOMOLOGOUS SERIES OF COMPOUNDS HAVING C6-18, A BIPHASIC STRUCTURE-FUNCTION RELATIONSHIP WAS FOUND, WITH MAXIMUM COMITOGENIC ACTIVITY OCCURRING FOR TETRADECANE. THE CONCN OF TETRADECANE HAVING EQUIVALENT COMITOGENIC ACTIVITY WAS SIMILAR TO THAT OF METHYL MYRISTATE.

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 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5,400(SRC), determined from a structure estimation method(2), indicates that methyl myristate is expected to be immobile in soil(SRC). Volatilization of methyl myristate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.005 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Methyl myristate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.00049 mm Hg(4). Methyl myristate is expected to rapidly biodegrade in aerobic soils by analogy to structurally similar long-chain fatty acid esters(5-7).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5400(SRC), determined from a structure estimation method(2), indicates that methyl myristate 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 0.005 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 6.2 days, respectively(SRC), using an estimation method(3). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The volatilization half-life from a model pond is estimated to be about 57 hours ignoring adsorption; when considering maximum adsorption the volatilization half-life increases to 45 days(5). According to a classification scheme(6), an estimated BCF of 540(SRC) from its log Kow of 6.41(12) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high although it may be lower than that indicated due to the expected rapid metabolism rate for long-chain fatty acid esters(10). Methyl myristate is expected to rapidly biodegrade in aerobic soils by analogy to structurally similar long-chain fatty acid esters(8-10). An estimated base-catalyzed second-order hydrolysis rate constant of 0.030 L/mole-sec(9,SRC) corresponds to half-lives of 7.3 years and 270 days at pH values of 7 and 8, respectively(11).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl myristate, which has a vapor pressure of 0.00049 mm Hg at 25 °C(2), will exist solely in the vapor phase in the ambient atmosphere. Vapor-phase methyl myristate 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 24 hours(SRC) from its estimated rate constant of 1.6X10-11 cu cm/molecule-sec at 25 °C(3).

Food Survey ValuesMethyl myristate was identified as a volatile component of clams, short neck clams, and corbicula(1).
Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Soil Adsorption/Mobility · 1 Eintrag

Using a structure estimation method based on molecular connectivity indices(1), the Koc for methyl myristate can be estimated to be about 5400(SRC). According to a classification scheme(2), this estimated Koc value suggests that methyl myristate is expected to be immobile in soil.

Regulatorische Informationen

FDA Requirements · 1 Eintrag

Methyl myristate is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

Sicherheitsdaten

wgk
1
tsca
TSCA listed
hs_code
29322090
risk_code
38
hazard_code
Xi
safety_code
23-24/25

Chemie und Industrie

Pharmakologische Informationen

Cellular LocationsExtracellular

Verwendung und Herstellung

Uses · 6 Einträge

CIR ingredient: Methyl Myristate

Used to make myristic acid detergents, emulsifiers, wetting agents, stabilizers, resins, lubricants, plasticizers, textiles, animal feeds, alkanolamides, and fatty alcohols and acids; Also used as standard for gas chromatography and for flavoring; [HSDB]

Textiles (Fiber & Fabric Manufacturing) [Category: Industry]

Intermediate for myristic acid detergents, emulsifiers, wetting agents, stabilizers, resins, lubricants, plasticizers, textiles, animal feeds; std for gas chromatography, flavoring.

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

FLAVORING AGENT, EG, IN CANDY & ICE CREAM

U.S. Production · 2 Einträge

2023: 1,000,000 - <8,500,000 lb

(1978) PROBABLY GREATER THAN 2.27X10+6 GRAMS

Consumer UsesSoftener and conditioner
Industry UsesEmulsifier
Methods of Manufacturing · 2 Einträge

BY DIRECT ESTERIFICATION OF METHANOL WITH MYRISTIC ACID IN PRESENCE OF GASEOUS HYDROGEN CHLORIDE.

...ALCOHOLYSIS OF COCONUT OIL WITH METHANOL. METHOD OF PURIFICATION: VACUUM FRACTIONAL DISTILLATION.

Formulations/PreparationsGrades: Technical (93%); Purified (99.8%)
Anwendungen · 3 Einträge

BeschreibungMethyl myristate has a honey and orris-like odor with a corresponding flavor at trace levels. May be prepared by direct esterification of methanol with myristic acid in the presence of gaseous HCL.

VerwendenMethyl myristate may be used as an intermediate polarity oil component of oil-in-water, especially “Pickering-type”, emulsions.

VerwendenMethyl myristate finds limited use in perfume compositions, not only in Orris bases with Ionones, but also in Mimosa, Cassie, Tuberose, Honey-suckle, etc. It performs well in powder perfumes with musks and Methylionones. The ester finds some use in flavor compositions, mainly in Honey and a few types of fruit flavor. The concentration is normally only traces, or from 0.2 to 2 ppm.

Darstellung

synthetischeBy direct esterification of methanol with myristic acid in the presence of gaseous HCl.

Ergänzende Hinweise

DefinitionThemethyl ester of myristic acid.

Zugehörige Reaktionen

9

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