Identification

Namemethyl acetoacetate
IUPACmethyl 3-oxobutanoate
CAS Number105-45-3
EINECS203-299-8
FDA UNIICW4I82QAX1
Molecular FormulaC5 H8 O3
Molecular Weight116.11636000
MDL NumberMFCD00008784
Nikkaji NumberJ45.957G
Beilstein0506727

Regulatory

DG SANTE Food Flavourings09.634 methyl acetoacetate

Physical Properties

Appearance colorless clear liquid (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Specific Gravity 1.07300 to 1.07900 @ 25.00 °C.
Pounds per Gallon - (est). 8.928 to 8.978
Refractive Index 1.41500 to 1.42100 @ 20.00 °C.
Melting Point -80.00 °C. @ 760.00 mm Hg
Boiling Point 169.00 °C. @ 760.00 mm Hg
Vapor Pressure 1.543000 mmHg @ 25.00 °C. (est)
Flash Point 150.00 °F. TCC ( 65.56 °C. )
logP (o/w) 0.185 (est)
Soluble in alcohol
Insoluble in water
Similar Items note

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesperfuming agents

Organoleptic Properties

Odor Strength medium
Substantivity 4 hour(s) at 100.00 %
Odor Description at 100.00 %.

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Oral/Parenteral Toxicityoral-rat LD50 2800 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorycosmetic, flavor and fragrance agents
RIFM Fragrance Material Safety AssessmentSearch
Recommendation for methyl acetoacetate usage levels up to2.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU)0.012 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI)3900 (μg/person/day)
Threshold of Concern1800 (μg/person/day)
Structure ClassI
Dairy products, excluding products of category 02.0 (01.0)7.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0)5.00000
Edible ices, including sherbet and sorbet (03.0)10.00000
Processed fruit (04.1)7.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2)-
Confectionery (05.0)10.00000
Chewing gum (05.3)-
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0)5.00000
Bakery wares (07.0)10.00000
Meat and meat products, including poultry and game (08.0)2.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0)2.00000
Eggs and egg products (10.0)-
Sweeteners, including honey (11.0)-
Salts, spices, soups, sauces, salads, protein products, etc. (12.0)5.00000
Foodstuffs intended for particular nutritional uses (13.0)10.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1)5.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2)10.00000
Ready-to-eat savouries (15.0)20.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0)5.00000

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Potential Uses

FL citrus FR fruit FL herbal FL lemon FL orange

Natural Occurrence

not found in nature

Synonyms

acetoacetic acid methyl ester 3-oxo butanoic acid methyl ester butanoic acid, 3-oxo-, methyl ester 3-oxo- butyric acid methyl ester MAA 1- methoxybutane-1,3-dione methyl 3-oxobutanoate methyl 3-oxobutyrate methyl acetyl acetate methyl acetylacetate methylacetoacetate PubMed: Stereodivergent Synthesis and Relative Stereostructure of the C1-C13 Fragment of Symbiodinolide. PubMed: Presolvated electron reactions with methyl acetoacetate: electron localization, proton-deuteron exchange, and H-atom abstraction. PubMed: NADPH-dependent reductive biotransformation with Escherichia coli and its pfkA deletion mutant: influence on global gene expression and role of oxygen supply. PubMed: Synthesis, characterization, and antimicrobial evaluation of a small library of ferrocene-containing acetoacetates and phenyl analogs: the discovery of a potent anticandidal agent. PubMed: SoxR as a single-cell biosensor for NADPH-consuming enzymes in Escherichia coli. 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PubMed: Inhibition of energy metabolism by 2-methylacetoacetate and 2-methyl-3-hydroxybutyrate in cerebral cortex of developing rats. PubMed: Purification and cDNA cloning of NADPH-dependent aldoketoreductase, involved in asymmetric reduction of methyl 4-bromo-3-oxobutyrate, from Penicillium citrinum IFO4631. PubMed: Peroxynitrite-initiated oxidation of acetoacetate and 2-methylacetoacetate esters by oxygen: potential sources of reactive intermediates in keto acidoses. PubMed: Enantioselective reduction of carbonyl compounds by whole-cell biotransformation, combining a formate dehydrogenase and a (R)-specific alcohol dehydrogenase. PubMed: A modular and concise total synthesis of (+/-)-daurichromenic acid and analogues. PubMed: Rapid assembly of the bicyclo[5.3.1]undecenone core of penostatin F: a successive Diels-Alder/Claisen reaction strategy with an efficient stereochemical relay. PubMed: Domino Michael-Aldol reactions on 1,4-diarylbut-2-ene-1,4-diones with methyl acetoacetate furnish methyl 2-aroyl-4- hydroxy-6-oxo-4-arylcyclohexane-1-carboxylate derivatives. PubMed: Ruthenium-catalyzed one-pot double allylation/cycloisomerization of 1,3-dicarbonyl compounds leading to exo-methylenecyclopentanes. PubMed: Catalytic asymmetric Michael reaction of beta-keto esters: effects of the linker heteroatom in linked-BINOL. PubMed: Spectrophotometric and fluorimetric determination of hexamine in pure form and its pharmaceutical formulation. PubMed: A ring-closing metathesis approach toward formal total synthesis of (+)-diplodialide A. PubMed: First total syntheses of the phytotoxins solanapyrones D and E via the domino Michael protocol. PubMed: Synthesis, characterization and evaluation of antituberculosis activity of some hydrazones. PubMed: Reduction of ketones and alkyl iodides by SmI(2) and Sm(II)-HMPA complexes. Rate and mechanistic studies. PubMed: Stereospecific substitution of enantiomerically pure 1-(2-pyridinyl)ethyl methanesulfonate with beta-dicarbony compounds. PubMed: Metal-induced cyclization of thiosemicarbazones derived from beta-keto amides and beta-keto esters: open-chain and cyclized ligands in zinc(II) complexes. PubMed: Characterization of the aromatic profile in aqueous essence and fruit juice of yellow passion fruit (Passiflora edulis Sims F. Flavicarpa degner) by GC-MS and GC/O. PubMed: An unexpected [1,5]-h shift in the synthesis of nitroanilines. PubMed: Application of the Tethered Biginelli Reaction for Enantioselective Synthesis of Batzelladine Alkaloids. Absolute Configuration of the Tricyclic Guanidine Portion of Batzelladine B. PubMed: The first total synthesis of (-)-solanapyrone E based on domino Michael strategy. PubMed: Stereocontrolled reduction of alpha- and beta-keto esters with micro green algae, Chlorella strains. 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