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methyl butyrate

Chemical Structure

General Material Information

Preferred name methyl butyrate
Trivial Name Methyl butyrate
Short Description butyric acid, methyl ester
Formula C5 H10 O2
CAS Number 623-42-7
FEMA Number 2693
Flavis Number 9.038
ECHA Number 210-792-1
FDA UNII CGX598508O
Nikkaji Number J45.010C
Beilstein Number 1740743
MDL MFCD00009391
COE Number 263
NMR Predictor External link
JECFA Food Flavoring 149 methyl butyrate
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 623-42-7 ; METHYL BUTYRATE
Synonyms
  • butanoic acid methyl ester
  • butanoic acid, methyl ester
  • butyric acid methyl ester
  • N- butyric acid methyl ester
  • butyric acid, methyl ester
  • methyl butanoate
  • nat. methyl butyrate
  • methyl butyrate (natural)
  • methyl butyrate natural
  • methyl butyrate, natural
  • methyl N-butanoate
  • methyl N-butyrate
  • methyl-butyrate FCC
  • methyl-N-butanoate
  • methylbutanoat
  • Butyric acid, ester with MeOH
  • 3-Methylpropanoic acid methyl ester
  • NSC 9380

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

methyl butanoate
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:623-42-7
Pubchem (cid):12180
Pubchem (sid):134977109
Flavornet:623-42-7
Pherobase:View
Publications by Info
Volatile Flavor Components in Bogyojosaeng and Suhong Cultivars of Strawberry (Fragaria ananassa Duch.)
Publications by PubMed
Quantum Chemical Study of Autoignition of Methyl Butanoate.
Leucine Modulates Mitochondrial Biogenesis and SIRT1-AMPK Signaling in C2C12 Myotubes.
Comparative essential oil composition of aerial parts of Tanacetum dumosum Boiss. from Southern Zagros, Iran.
Theoretical study of the rate constants for the hydrogen atom abstraction reactions of esters with (•)OH radicals.
Characterization of aroma compounds of Chinese famous liquors by gas chromatography-mass spectrometry and flash GC electronic-nose.
Theoretical and kinetic study of the hydrogen atom abstraction reactions of esters with H(O.)2 radicals.
Leucine and HMB differentially modulate proteasome system in skeletal muscle under different sarcopenic conditions.
Medications affecting functional status in older persons.
Analysis and sensory evaluation of jostaberry (Ribes x nidigrolaria Bauer) volatiles.
The effectiveness of natural and synthetic immunomodulators in the treatment of inflammatory bowel disease in dogs.
Gas signatures from Escherichia coli and Escherichia coli-inoculated human whole blood.
Redirecting catalysis from proteolysis to perhydrolysis in subtilisin Carlsberg.
Solvent-Free Synthesis of Flavour Esters through Immobilized Lipase Mediated Transesterification.
Quantitative analysis of fragrance and odorants released from fresh and decaying strawberries.
Abelmoschus esculentus (L.) Moench. and Abelmoschus moschatus Medik: seeds production and analysis of the volatile compounds.
Analysis and sensory evaluation of gooseberry (Ribes uva crispa L.) volatiles.
Reaction pathways for the thermal decomposition of methyl butanoate.
Characterization of Aronia melanocarpa volatiles by headspace-solid-phase microextraction (HS-SPME), simultaneous distillation/extraction (SDE), and gas chromatography-olfactometry (GC-O) methods.
Body composition of piglets from sows fed the leucine metabolite β-hydroxy β-methyl butyrate in late gestation.
Effect of β-hydroxy β-methyl butyrate supplementation of sows in late gestation and lactation on sow production of colostrum and milk and piglet performance.
Effects of β-hydroxy β-methyl butyrate supplementation to sows in late gestation on absorption and hepatic metabolism of glucose and amino acids during transition.
High-temperature measurements of the reactions of OH with small methyl esters: methyl formate, methyl acetate, methyl propanoate, and methyl butanoate.
Identification and quantification of odorous compounds from adhesives used in food packaging materials by headspace solid phase extraction and headspace solid phase microextraction coupled to gas chromatography-olfactometry-mass spectrometry.
Synergistic effects of leucine and resveratrol on insulin sensitivity and fat metabolism in adipocytes and mice.
1-methylcyclopropene effects on temporal changes of aroma volatiles and phytochemicals of fresh-cut cantaloupe.
Development and validation of LC-MS/MS method for the estimation of β-hydroxy-β-methylbutyrate in rat plasma and its application to pharmacokinetic studies.
An in vitro evaluation of the effect of probiotics and prebiotics on the metabolic profile of human microbiota.
Beta-hydroxy-beta-methyl-butyrate blunts negative age-related changes in body composition, functionality and myofiber dimensions in rats.
Evaluation of volatiles from two subtropical strawberry cultivars using GC-olfactometry, GC-MS odor activity values, and sensory analysis.
Headspace-solid phase microextraction coupled to gas chromatography-combustion-isotope ratio mass spectrometer and to enantioselective gas chromatography for strawberry flavoured food quality control.
Aroma profile and volatiles odor activity along gold cultivar pineapple flesh.
Fuel-specific influences on the composition of reaction intermediates in premixed flames of three C5H10O2 ester isomers.
Key aroma components of a dry-cured sausage with high fat content (sobrassada).
Effects of gestation and transition diets, piglet birth weight, and fasting time on depletion of glycogen pools in liver and 3 muscles of newborn piglets.
Comparison of volatile components in Chinese traditional pickled peppers using HS-SPME-GC-MS, GC-O and multivariate analysis.
RP-HPLC/MS-APCI analysis of branched chain TAG prepared by precursor-directed biosynthesis with Rhodococcus erythropolis.
Impact of postharvest methyl jasmonate treatment on the volatile composition and flavonol content of strawberries.
Study on the constituents of Mexican propolis and their cytotoxic activity against PANC-1 human pancreatic cancer cells.
Influence of modified atmosphere packaging on volatile compounds and physicochemical and antioxidant attributes of fresh-cut pineapple (Ananas comosus).
The phenylpropanoids of Aster flaccidus.
Chemical characterization, antioxidant properties, and volatile constituents of naranjilla (Solanum quitoense Lam.) cultivated in Costa Rica.
Construction of combustion models for rapeseed methyl ester bio-diesel fuel for internal combustion engine applications.
Lipoxygenase gene expression in ripening kiwifruit in relation to ethylene and aroma production.
Comparative analysis of the volatile fraction from Annona cherimola Mill. cultivars by solid-phase microextraction and gas chromatography-quadrupole mass spectrometry detection.
Kinetic modeling of methyl butanoate in shock tube.
Inhibition of NF-kappaB-mediated transcription and induction of apoptosis in human breast cancer cells by epoxypseudoisoeugenol-2-methyl butyrate.
Immobilization of Candida antarctica lipase B by adsorption to green coconut fiber.
A randomized, double-blind, placebo-controlled trial of a beta-hydroxyl beta-methyl butyrate, glutamine, and arginine mixture for the treatment of cancer cachexia (RTOG 0122).
Wavelength dependence of light-induced lipid oxidation and naturally occurring photosensitizers in cheese.
A new irreversible enzyme-aided esterification method in organic solvents.
3-Mesityl-2-oxo-1-oxaspiro-[4.4]non-3-en-4-yl 2-(4-chloro-phen-yl)-3-methyl-butyrate.
Thermal decomposition of methyl butanoate: ab initio study of a biodiesel fuel surrogate.
The effects of in ovo feeding arginine, beta-hydroxy-beta-methyl-butyrate, and protein on jejunal digestive and absorptive activity in embryonic and neonatal turkey poults.
Correlating volatile compounds, sensory attributes, and quality parameters in stored fresh-cut cantaloupe.
Identification of pig liver esterase variants by tandem mass spectroscopy analysis and their characterization.
Enthalpies of formation, bond dissociation energies and reaction paths for the decomposition of model biofuels: ethyl propanoate and methyl butanoate.
Experimental and modeling study of C5H10O2 ethyl and methyl esters.
[Changes in amino acid and fatty acid contents as well as activity of some related enzymes in apple fruit during aroma production].
Gas chromatographic-mass spectrometric analysis of essential oils from Pimpinella aurea, Pimpinella corymbosa, Pimpinella peregrina and Pimpinella puberula gathered from Eastern and Southern Turkey.
Parallel synthesis: a new approach for developing analytical internal standards. Application to the analysis of patulin by gas chromatography-mass spectrometry.
Dietary toxicity of calcium beta-hydroxy-beta-methyl butyrate (CaHMB).
Flavor release and rheology behavior of strawberry fatfree stirred yogurt during storage.
Recombinant porcine intestinal carboxylesterase: cloning from the pig liver esterase gene by site-directed mutagenesis, functional expression and characterization.
Headspace gas chromatography-mass spectrometry of volatile compounds in murici (Byrsonima crassifolia l. Rich).
Quality assessment of strawberries (Fragaria species).
Influence of harvest date and light integral on the development of strawberry flavour compounds.
Gas-phase reactivity of the O=P(OCH3)2+ phosphonium ion with aliphatic esters in a quadrupole ion trap. Spontaneous elimination of ketenes.
[Separation and identification of thellungianin G from the root of Pimpinella thellungiana Wolff].
Studies of the constituents of Uruguayan propolis.
Studies on taxol biosynthesis. Preparation of taxa-4(20),11(12)-dien-5 alpha-acetoxy-10 beta-ol by deoxygenation of a taxadiene tetraacetate obtained from Japanese yew.
Total synthesis of (-)-bafilomycin A(1).
Volatile compounds of selected strawberry varieties analyzed by purge-and-trap headspace GC-MS.
Aromatic profile of aqueous banana essence and banana fruit by gas chromatography-mass spectrometry (GC-MS) and gas chromatography-olfactometry (GC-O).
Biotransformation of MTBE, ETBE, and TAME after inhalation or ingestion in rats and humans.
Olfaction in the Queensland fruit fly, Bactrocera tryoni. II: Response spectra and temporal encoding characteristics of the carbon dioxide receptors.
Olfaction in the Queensland fruit fly, Bactrocera tryoni. I: Identification of olfactory receptor neuron types responding to environmental odors.
Dielectric properties of some components of fruit aroma in carbon tetrachloride solution at 298.15 K.
In vitro effects of beta-hydroxy-beta-methylbutyrate (HMB) on cell-mediated immunity in fish.
Use of creatine and other supplements by members of civilian and military health clubs: a cross-sectional survey.
Modeling flavor release from aqueous sucrose solutions, using mass transfer and partition coefficients.
Decyl-thio-trifluoropropanone, a competitive inhibitor of moth pheromone receptors.
Effect of superficial scald suppression by diphenylamine application on volatile evolution by stored Cortland apple fruit.
Dietary supplements and the promotion of muscle growth with resistance exercise.
Assimilation of volatiles from ripe apples by Sporidiobolus salmonicolor and Tilletiopsis washingtonensis.
Lipoxygenase inhibitors, Part 6. Synthesis of new tetrahydropyrazine and other heterocyclic compounds by reaction of hydrazonoyl chlorides.
Biochemistry of esterases associated with organophosphate resistance in Lucilia cuprina with comparisons to putative orthologues in other Diptera.
[Separation and identification of the llungianin A and B from the root of Pimpinella thellungiana Wolff].
Cholesterol quantitation by GLC: artifactual formation of short-chain steryl esters.
Colostral milk fat percentage and pig performance are enhanced by feeding the leucine metabolite beta-hydroxy-beta-methyl butyrate to sows.
Effects of beta-hydroxy-beta-methyl butyrate on performance and carcass quality of feedlot steers.
A cluster of esterase genes on chromosome 3R of Drosophila melanogaster includes homologues of esterase genes conferring insecticide resistance in Lucilia cuprina.
A note on the identity of porcine liver carboxylesterase and prolyl-beta-naphthylamidase.
Novel anticancer prodrugs of butyric acid. 2.
Host-derived volatiles as attractants and pheromone synergists for driedfruit beetleCarpophilus hemipterus.
Immobilization of lipase from Candida cylindraceae and its use in the synthesis of menthol esters by transesterification.
Analysis of beta-hydroxy-beta-methyl butyrate in plasma by gas chromatography and mass spectrometry.
Influence of protein percentage and degradability on performance of lactating cows during moderate temperature.
Subcellular localization of non-specific carboxylesterases, acylcarnitine hydrolase, monoacylglycerol lipase and palmitoyl-CoA hydrolase in rat liver.
Purification of rat kidney carboxylesterase and its comparison with other tissue esterases.
Net portal absorption of volatile fatty acids and L(+)-lactate by lactating Holstein cows.
Carboxylesterases in guinea-pig plasma and liver. Tissue specific reactivation by diacetylmonoxime after soman inhibition in vitro.
Purification and characterization of a carboxylesterase from rabbit liver lysosomes.
Local anesthetic action of carboxylic esters: evidence for the significance of molecular volume and for the number of sites involved.
Esterase activities and soman toxicity in developing rat.
A radiochemical assay method for carboxylesterase, and comparison of enzyme activity towards the substrates methyl [1-14C] butyrate and 4-nitrophenyl butyrate.
Beclobrinic acid--a new hypolipidemic agent--inhibits in vitro human platelet activation by blocking prostaglandin synthesis.
Methyl butyrate-hydrolyzing activity of hepatic triglyceride lipase from rat post-heparin plasma.
Effect of Brij 58 on the hydrolysis of methyl butyrate by lipase from Pseudomonas fluorescens.
Effect of carbon-4 and carbon-5 volatile fatty acids on growth of mixed rumen bacteria in vitro.
Purification and some properties of intracellular esterase from Pseudomonas fluorescens.
Ruminal VFA production with steers fed whole or ground corn grain.
Identification of the chloramphenicol-hydrolyzing enzyme of guinea pig liver as one of the nonspecific carboxylesterases.
Characteristics of the rumen proteolysis of fraction I (18S) leaf protein from lucerne (Medicago sativa L).
Effect of alcohols on the hydrolysis catalyzed by human pancreatic carboxylic-ester hydrolase.
Studies on the substrate specificity of a carboxyl ester hydrolase from human pancreatic juice. I. Action on carboxyl esters, glycerides and phospholipids.
Adaptation and cross-adaptation to odor stimulation of olfactory receptors in the tiger salamander.
Candletoxins A and B, 2 new aromatic esters of 12-deoxy-16-hydroxy-phorbol, from the irritant latex of Euphoria poisonii Pax.
The succulent Euphorbias of Nigeria. II. aliphatic diterpene esters of the latices of E. poisonii Pax. and E. unispina N.E. Br.
Subcellular fractionation, partial purification and characterization of neutral triacylglycerol lipase from pig liver.
Studies on lankacidin-group (T-2636) antibiotics. X. Microbial conversion of lankacidin-group antibiotics.
Quantitative analysis of cholesterol in 5 to 20 microliter of plasma.
Cell-bound lipase and esterase of Brevibacterium linens.
Demonstration and function of 2-methyl-butyrate racemase in Ascaris lumbricoides.
Demonstration and function of 2-methyl-butyrate racemase in Ascaris lumbricoides.
Lipase from Pseudomonas fragi. II. Properties of the Enzyme.
Lipase of Mucor pusillus.
HYDROLYTIC ENZYMES OF RABBIT MONONUCLEAR EXUDATE CELLS. I. QUANTITATIVE ASSAY AND PROPERTIES OF CERTAIN PROTEASES, NON-SPECIFIC ESTERASES, AND LIPASES OF MONONUCLEAR AND POLYMORPHONUCLEAR CELLS AND ERYTHROCYTES.
The relation of alpha-methyl-butyrate to isoleucine metabolism. II. Propionate formation.
[Omega oxidation of methyl butyrate].
STUDIES ON ENZYME ACTION : XXXV. LIPASE ACTIONS OF EXTRACTS OF TISSUES OF RABBITS AT DIFFERENT AGES.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
HMDB (The Human Metabolome Database):HMDB33890
FooDB:FDB012084
YMDB (Yeast Metabolome Database):YMDB01743
Export Tariff Code:2915.60.0000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
grade: technical

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 102.13310241699
Specific gravity @ 25 °C
Pounds per Gallon 7.431 to 7.481
Refractive Index 1.385 to 1.39 @ 20 °C
Boiling Point 102 to 103°C @ 760 mm Hg
Boiling Point 33 to 34°C @ 50 mm Hg
Acid Value 1 max KOH/g
Vapor Pressure 31.136 mmHg @ 25 °C
Vapor Density 3.5
Flash Point TCC Value 11.67 °C TCC
logP (o/w) 1.29
Solubility
alcohol Yes
water, 9120 mg/L @ 25 °C (est) Yes
water, 1.50E+04 mg/L @ 25 °C (exp) Yes

Organoleptic Properties

Odor Type: Fruity
fruity, apple, sweet, banana, pineapple, pungent, ethereal, fusel, fermented, creamy
General comment At 10.00 % in dipropylene glycol. fruity apple sweet banana pineapple
Mosciano, Gerard P&F 23, No. 1, 33, (1998) At 1.00 %. Pungent, etherial, fruity, perfumey and fusel with a fermented, cultured, creamy undernote
Flavor Type: Fusel
fusel, fruity, estery, dairy, acidic
Mosciano, Gerard P&F 23, No. 1, 33, (1998) At 10.00 ppm. Impacting, fusel, fruity and estry with a cultured dairy, acidic depth

Occurrences

Potential Uses

Applications
Odor purposes Currant , Melon , Passion fruit
Flavoring purposes Apple , Banana , Berry mixed berry , Cheese blue cheese , Cheese cheddar cheese , Coffee , Cranberry , Fig , Grape , Guava , Huckleberry , Nut , Olive , Papaya , Pineapple , Pumpkin , Quince , Raspberry , Rum , Tutti frutti
Other purposes Feyoa
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 11 - Highly flammable.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 16 - Keep away from sources of ignition - No Smoking.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Human Experience:
8 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 > 5000 mg/kg
Food and Chemical Toxicology. Vol. 20, Pg. 741, 1982.

oral-rabbit LD50 3380 mg/kg
Industrial Medicine and Surgery. Vol. 41, Pg. 31, 1972.

Dermal Toxicity:
skin-rabbit LD50 3560 mg/kg
Toxicology and Applied Pharmacology. Vol. 42, Pg. 417, 1977.

Inhalation Toxicity:
inhalation-mouse LC50 18000 mg/m3/2H
"Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 81, 1982.

inhalation-mammal (species unspecified) LC50 20000 mg/m3
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(5), Pg. 61, 1986.

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for methyl butyrate usage levels up to:
2.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 220.00 (μg/capita/day)
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: 48.00000200.00000
beverages(nonalcoholic): -17.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -31.00000
fruit ices: -31.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -86.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 2, Revision 1 (FGE.02) : Branched- and straight-chain aliphatic saturated primary alcohols and related esters of primary alcohols and straight-chain carboxylic acids and one straight-chain aldehyde from chemical groups 1 and 2 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Scientific Opinion on the safety and efficacy of straight-chain primary aliphatic alcohols/aldehydes/acids, acetals and esters with esters containing saturated alcohols and acetals containing saturated aldehydes (chemical group 1) when used as flavourings for all animal species
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):623-42-7
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :12180
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1237
WGK Germany:2
methyl butanoate
Chemidplus:0000623427
EPA/NOAA CAMEO:hazardous materials
RTECS:ET5500000 for cas# 623-42-7