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Methyllaurat

Methyl Laurate

HCID 8139
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Grundinformationen

CAS
111-82-0
Standard-SMILES
CCCCCCCCCCCC(=O)OC
InChIKey
UQDUPQYQJKYHQI-UHFFFAOYSA-N
Summenformel
C13H26O2
Durchschnittliche Molmasse
214,34 g/mol
Monoisotopische Masse
214,19328007

Überblick

Methyl laurate is a fatty acid methyl ester of lauric acid. It has a role as a metabolite. It is a fatty acid methyl ester and a dodecanoate ester.

Namen und Bezeichner

Bevorzugter Name
Methyl Laurate
IUPAC
methyl dodecanoate
Lokaler Name
Methyllaurat
Englischer Name
Methyl laurate
Summenformel
C13H26O2
Molmasse
214.34

Namen und Synonyme

Methyl laurateMETHYL DODECANOATE111-82-0Lauric acid methyl esterDodecanoic acid, methyl esterMethyl laurinateMethyl dodecylateMethyl n-dodecanoateUniphat A40Metholene 2296Lauric acid, methyl esterStepan C40
Weitere Namen anzeigen
DODECANOIC ACID METHYL ESTERC13H26O2FEMA 2715stepanc40uniphata40Dodecanoic ac
FEMA number 2715FEMA No. 2715DTXSID50268898IPS6BI6KWformyl dodecanoateNSC-5027DTXCID206889CHEBI:87494

Datenbank-Bezeichner

CAS
111-82-0
PubChem CID
8139
DTXSID
DTXSID5026889
ChEMBL
CHEMBL1894365
ChEBI
CHEBI:87494
UNII
8IPS6BI6KW
EC Number
203-911-3
Nikkaji
J374C

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,8
Polarare Oberfläche (TPSA)
26,3 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
11
Schwere Atome
15
Formalladung
0
Komplexität
143

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Esters, Other
LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Short fatty esters [FA0710]
CosmeticsEmollient; Skin conditioning
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Methyl laurate) -> IFRA transparency List
LogP · 3 Einträge

log Kow= 5.41

5.41

5.41

Odor · 2 Einträge

FATTY, FLORAL ODOR REMINISCENT OF WINE

OILY, WINEY, FATTY ODOR

TasteFATTY TASTE
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 2 Einträge

0.8702 @ 20 °C/4 °C

0.863-0.872

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 12.2% (52 of 426) of reports.

Warning

H400 (74.6%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

P273, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 426 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: Dodecanoic acid, methyl ester

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

REACH registered substance: Methyl laurate (EC: 203-911-3)

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

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

Methyl laurate 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.

Chemie und Industrie

Pharmakologische Informationen

Cellular LocationsExtracellular

Verwendung und Herstellung

Uses · 4 Einträge

Made from coconut oil; [Hawley] Used as a flavoring agent and as an intermediate for detergents, emulsifiers, wetting agents, stabilizers, lubricants, plasticizers, textiles, alkanolamides, fatty alcohols, and acids; [HSDB]

Intermediate for detergents, emulsifiers, wetting agents, stabilizers, lubricants, plasticizers, textiles, flavoring

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

FLAVORING AGENT, EG, IN BAKED GOODS & ICE CREAM

U.S. Production2023: 40,000,000 - <55,000,000 lb
Consumer UsesBinder
Industry UsesLubricating agent
Methods of ManufacturingBY PROLONGED BOILING OF LAURIC ACID WITH METHANOL IN THE PRESENCE OF SULFURIC ACID.
Formulations/PreparationsGrades: 69%, 74%, 90%, 96%, 99.8%
Use Classification · 6 Einträge

EPA Safer Chemical Functional Use Classes -> Emollients;Skin Conditioning Agents;Solvents

Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Cosmetics -> Emollient; Skin conditioning

General Manufacturing Information · 5 Einträge

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

Dodecanoic acid, methyl ester: ACTIVE

Zugehörige Reaktionen

11
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 373192
HRID 373192als Eduktuspto-grants-1992_11
Reaktionsgleichung von HRID 654278
HRID 654278als Eduktuspto-grants-1992_07
Reaktionsgleichung von HRID 871069
HRID 871069als Produktuspto-grants-2015_03
Reaktionsgleichung von HRID 1048638
HRID 1048638als Eduktuspto-grants-2016_07
Reaktionsgleichung von HRID 1500154
HRID 1500154als Eduktuspto-grants-2015_12
Reaktionsgleichung von HRID 1548402
HRID 1548402als ProduktTraining data from https://doi.org/10.1039/C8SC04228D (1/10)
Reaktionsgleichung von HRID 1656304
HRID 1656304als Produktuspto-grants-1993_10
Reaktionsgleichung von HRID 2116743
HRID 2116743als Eduktuspto-grants-2008_10
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Flavoring AgentsEU Flavoring substances
Color/Form · 2 Einträge

COLORLESS LIQUID

Water-white liquid

Physikochemische Eigenschaften

Schmelzpunkt
4 · 4-5 °C (lit.)
Siedepunkt
262 °C/766 · 262 °C/766 mmHg (lit.)
Dichte
0.87 g/mL · 0.87 g/mL at 25 °C (lit.)
Dampfdruck
0.55 Pa · 0.55Pa at 25℃
Brechungsindex
20 · n20/D 1.432
FEMA
2715 · 2715 | METHYL LAURATE
Flammpunkt
230 °F · >230 °F
storage temp.
room temp
Löslichkeit
0.00759 g/L · water: insoluble0.00759g/L at 25°C (practically)
Aggregatzustand
Liquid
Farbe
Clear colorless to slightly yellow
Geruch (Odor)
100 % · at 100.00 %. waxy soapy creamy coconut mushroom
Geruchsart
waxy
Biologische Quelle
synthetic
Wasserlöslichkeit
Not miscible in water. Soluble in alcohol, dipropylene glycol.
JECFA Number
180 · 180
BRN
1767780 · 1767780
Henry's Law Constant
8.3 · 8.3×10-3 mol/(m3Pa) at 25℃, Krop and Velzen (1997)
Dielectric constant
3.6 · 3.6000000000000001
Major Application
flavors and fragrances
Kosmetik-Inhaltsstoffe Funktionen
SKIN CONDITIONINGPERFUMINGSKIN CONDITIONING - EMOLLIENT
InChI
1S/C13H26O2/c1-3-4-5-6-7-8-9-10-11-12-13(14)15-2/h3-12H2,1-2H3
InChIKey
UQDUPQYQJKYHQI-UHFFFAOYSA-N
SMILES
CCCCCCCCCCCC(=O)OC
LogP
5.41 at · 5.41 at 36℃
CAS Datenbank
111 · 111-82-0(CAS DataBase Reference)
EPA chemische Informationen
Methyl laurate (111-82-0)
EPA Safer ChemicalChemical: Methyl laurate
Hazard Classes and Categories · 4 Einträge

Aquatic Acute 1 (74.6%)

Skin corrosion/irritation - Category 2

Hazardous to the aquatic environment (Acute) - Category 1

Specific target organ toxicity - Single exposure - Category 3 (Narcotic effects)

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

Interactions · 1 Eintrag

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 1,600(SRC), determined from a structure estimation method(2), indicates that methyl dodecanoate is expected to be immobile in soil(SRC). Volatilization of methyl dodecanoate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.003 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Methyl dodecanoate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.004 mm Hg(4). Methyl dodecanoate 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 1,600(SRC), determined from a structure estimation method(2), indicates that methyl dodecanoate 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 0.003 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). 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 56 hours ignoring adsorption; when considering maximum adsorption the volatilization half-life increases to 14 days(5). According to a classification scheme(6), an estimated BCF of 290(SRC) from its log Kow of 5.41(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 this compound(9). Methyl dodecanoate 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 dodecanoate, which has a vapor pressure of 0.0041 mm Hg at 25 °C(2), will exist in solely as a vapor in the ambient atmosphere. Vapor-phase methyl dodecanoate 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 29 hours(SRC) from its estimated rate constant of 1.3X10-11 cu cm/molecule-sec at 25 °C(3).

Soil Adsorption/Mobility · 1 Eintrag

Using a structure estimation method based on molecular connectivity indices(1), the Koc for methyl dodecanoate can be estimated to be about 1600(SRC). According to a classification scheme(2), this estimated Koc value suggests that methyl dodecanoate is expected to have low mobility in soil.

Natural Pollution SourcesREPORTED FOUND IN ORRIS ABSOLUTE.
Artificial Pollution SourcesMethyl dodecanoate's production and use as a synthetic intermediate and flavoring(1) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationAEROBIC: By analogy to chemically similar long chain fatty acid esters that were rapidly degraded by mixed sewage sludge(1-3), methyl dodecanoate is expected to rapidly biodegrade under aerobic conditions(SRC).
Sediment/Soil ConcentrationsSOIL: Methyl dodecanoate was qualitatively detected in soil samples from Southern Alberta, Canada, in strata associated with the Mazama volcano eruption which occurred approximately 7000 years ago(1).
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Environmental Bioconcentration · 1 Eintrag

An estimated BCF of 290 was calculated for methyl dodecanoate(SRC) using a log Kow of 5.41(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 high. However, bioconcentration studies on compounds which are structurally similar(4,5) suggests 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(SRC).

Volatilization from Water/Soil · 1 Eintrag

The Henry's Law constant for methyl dodecanoate is estimated as 0.003 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that methyl dodecanoate 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). The volatilization half-life from a model pond 2 m deep is estimated to be about 56 hours ignoring adsorption; when considering maximum adsorption the volatilization half-life increases to 14 days(3). Methyl dodecanoate's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur although adsorption is expected to attenuate this process(SRC). Methyl dodecanoate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.0041 mm Hg(4).

Non-Human Toxicity Excerpts · 2 Einträge

USING DEPRESSED GROWTH RESPONSE AS A CRITERION, THE EFFECTS OF METHYL ESTERS OF FATTY ACIDS OF CHAIN LENGTH 4 TO 18 CARBONS ON ESSENTIAL FATTY ACID DEFICIENCY WERE STUDIED. HIGH MORTALITY WAS OBSERVED IN RATS FED METHYL LAURATE. IT ACCENTUATED THE ESSENTIAL FATTY ACID DEFICIENCY BECAUSE SUPPLEMENTATION RESULTED IN AN INCR ACCUMULATION OF HEPATIC CHOLESTEROL ESTERS.

INTRAVENOUS INJECTION OF 1.2 MG METHYL LAURATE PRODUCED IMMEDIATE DEATH IN MICE.

Environmental Abiotic Degradation · 1 Eintrag

The rate constant for the vapor-phase reaction of methyl dodecanoate with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 29 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.030 L/mole-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). Methyl dodecanoate is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum(3).

Regulatorische Informationen

FDA Requirements · 1 Eintrag

Methyl laurate 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
ridadr
UN 3082 9 / PGIII
hs_code
2915 90 30
RTECS-Nr.
OF0670000
risk_code
50
Toxizität
LD50 orally in Rabbit: > 2000 mg/kg
hazard_code
N
safety_code
24/25-61
Speicherklasse
10 - Combustible liquids
Giftige Stoffe Daten
111-82-0(Hazardous Substances Data)
Hazard Classifications
Aquatic Acute 1Aquatic Chronic 2

Method of purification: vacuum fractional distillation.

NON-ALCOHOLIC BEVERAGES 0.50-5.0 PPM; ICE CREAM, ICES, ETC 0.50-5.0 PPM; CANDY 0.02-0.50 PPM; BAKED GOODS 1.0 PPM.

USEFUL IN FATTY FLAVORS, COCONUT, NUT.

Anwendungen · 3 Einträge

BeschreibungMethyl laurate has a fatty, floral odor reminiscent of wine. May be prepared by prolonged boiling of lauric acid with methanol in the presence of sulfuric acid. Methyl Laurate is a flavour ketone produced in a reaction biocatalyzed by microencapsulated fungal spores. Also used in production of biodiesel.

OccurrenceReported found in orris absolute, strawberry, apple, bilberry, rum, coconut, grapes, melon, papaya, pineapple, blackberry, mustard, cheeses, hop oil, cognac, white wine, cocoa, oats, plumcot, elderberry juice, loquat, babaco fruit (Carica pentagona Heilborn), Bourbon vanilla, mountain papaya, Chinese cabbage, mussels, cape gooseberry, pawpaw, banana, berries and blue cheese

VerwendenMethyl laurate has been used in selective synthesis of the secondary amide surfactant, N-methyl lauroylethanolamide.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

LaurinsureMethanolEthyllaurat

Nachgelagerte Produkte

1-Dodecanol2-MorpholinoethansulfonsaeureDodecyllauratcis-7,10,13,16,19-Docosapentaenoic acid methyl ester

Ergänzende Hinweise

DefinitionChEBI: A fatty acid methyl ester of lauric acid.