EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

methyl acetoacetate
butanoic acid, 3-oxo-, methyl ester

Sponsors

Name:methyl 3-oxobutanoate
CAS Number: 105-45-3Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:203-299-8
FDA UNII:CW4I82QAX1
Nikkaji Web:J45.957G
Beilstein Number:0506727
MDL:MFCD00008784
Molecular Weight:116.11636000
Formula:C5 H8 O3
NMR Predictor:Predict (works with chrome or firefox)
Category:cosmetic, flavor and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
FLAVIS Number:09.634 (Old)
DG SANTE Food Flavourings:09.634 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 mm/Hg @ 25.00 °C. (est)
Flash Point: 150.00 °F. TCC ( 65.56 °C. )
logP (o/w): 0.185 (est)
Soluble in:
 alcohol
 water, 4.06e+005 mg/L @ 25 °C (est)
Insoluble in:
 water
Similar Items:note
amyl acetoacetate
isoamyl acetoacetate
para-anisyl acetoacetate
benzyl acetoacetate
bergamot acetoacetate
butyl acetoacetate
isobutyl acetoacetate
cinnamyl acetoacetate
cyclohexyl acetoacetate
dodecyl acetoacetate
ethyl 2-ethyl acetoacetate
ethyl acetoacetate
geranyl acetoacetate
heptyl acetoacetate
(Z)-3-hexen-1-yl acetoacetate
hexyl acetoacetate
jasmin acetoacetate
laevo-menthyl acetoacetate
spicy acetoacetate
 
Organoleptic Properties:
Odor Type: fruity
Odor Strength:medium
Substantivity:4 hour(s) at 100.00 %
fresh fruity citrus green
Odor Description:at 100.00 %. fresh fruity citrus green
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: perfuming agents
 
Suppliers:
BOC Sciences
For experimental / research use only.
Methyl Acetoacetate
Charkit Chemical
METHYL ACETOACETATE
Eastman Chemical
Eastman™ MAA (Methyl Acetoacetate)
EMD Millipore
For experimental / research use only.
Methyl Acetoacetate
OQEMA
Methyl Acetoacetate
Penta International
METHYL ACETOACETATE
Santa Cruz Biotechnology
For experimental / research use only.
Methyl Acetoacetate 99%
Sigma-Aldrich: Aldrich
For experimental / research use only.
Methyl Acetoacetate ReagentPlus®, 99%
TCI AMERICA
For experimental / research use only.
Methyl Acetoacetate >99.0%(GC)
Tengzhou Xiang Yuan Aroma Chemicals
Methyl Acetoacetate
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36 - Irritating to eyes.
S 02 - Keep out of the reach of children.
S 25 - Avoid contact with eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 37/39 - Wear suitable gloves and eye/face protection.
 
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.
Oral/Parenteral Toxicity:
oral-rat LD50 2800 mg/kg
(BASF, 1978)

oral-rat LD50 3000 mg/kg
(Smyth & Carpenter, 1948)

oral-rat LD50 3228 mg/kg
Journal of Industrial Hygiene and Toxicology. Vol. 30, Pg. 63, 1948.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: cosmetic, flavor and fragrance agents
Recommendation for methyl acetoacetate usage levels up to:
  2.0000 % 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 Concern:1800 (μg/person/day)
Structure Class: I
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 7.0000035.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 5.0000025.00000
Edible ices, including sherbet and sorbet (03.0): 10.0000050.00000
Processed fruit (04.1): 7.0000035.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 10.0000050.00000
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 5.0000025.00000
Bakery wares (07.0): 10.0000050.00000
Meat and meat products, including poultry and game (08.0): 2.0000010.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 2.0000010.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 5.0000025.00000
Foodstuffs intended for particular nutritional uses (13.0): 10.0000050.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 5.0000025.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 10.0000050.00000
Ready-to-eat savouries (15.0): 20.00000100.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 5.0000025.00000
 
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):

Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission related to - Flavouring Group Evaluation 10: Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf

Flavouring Group Evaluation 10, Revision 1 (FGE10 Rev1)[1] - Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 64 (FGE.64): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (57th meeting) structurally related to aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 evaluated by EFSA in FGE.10Rev1 (EFSA, 2008ab)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 92 (FGE.92): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (68th meeting) structurally related to aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones evaluated by EFSA in FGE.10Rev1 (2009)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 10, Revision 2 (FGE.10Rev2): Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 10, Revision 3 (FGE.10Rev3): Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30
View page or View pdf

EPI System: View
NIOSH International Chemical Safety Cards:search
NLM Hazardous Substances Data Bank:Search
Chemical Carcinogenesis Research Information System:Search
Env. Mutagen Info. Center:Search
EPA Substance Registry Services (TSCA):105-45-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7757
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
methyl 3-oxobutanoate
Chemidplus:0000105453
EPA/NOAA CAMEO:hazardous materials
RTECS:105-45-3
 
References:
 methyl 3-oxobutanoate
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:105-45-3
Pubchem (cid):7757
Pubchem (sid):134971160
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB00310
FooDB:FDB021937
Export Tariff Code:2918.30.9000
Haz-Map:View
ChemSpider:View
Formulations/Preparations:
available as liquid grades, assay 98%
 
Potential Blenders and core components note
For Odor
No odor group found for these
(Z)-8-
tetradecenal
FL/FR
(E)-
tiglaldehyde
FL/FR
aldehydic
aldehydic
dodecanal (aldehyde C-12 lauric)
FL/FR
(Z)-4-
dodecenal
FL/FR
green hexanal
FL/FR
undecanal
FL/FR
animal
para-
cresyl isobutyrate
FL/FR
balsamic
fir carboxylate
FR
citrus
citral diethyl acetal
FL/FR
citral dimethyl acetal
FL/FR
(R)-
citronellyl nitrile
FR
citronitrile (Symrise)
FR
iso
decyl acetate
FR
2-
dodecanone
FL/FR
limonene aldehyde
FR
(Z)-
linalool oxide (pyranoid)
FL/FR
litsea cubeba fruit oil
FL/FR
methyl heptenone
FL/FR
(Z+E)-2-
methyl-2-(4-methyl-3-pentenyl) cyclopropane carbaldehyde
FL/FR
1-
methyl-4-methyl ethenyl cyclohexene sulfurized
FL/FR
alpha-
methylene citronellal
FR
nonanal dimethyl acetal
FL/FR
tangerine acetate
FR
creamy
3-
heptyl dihydro-5-methyl-2(3H)-furanone
FL/FR
fatty
3-
decen-2-one
FL/FR
hexyl pivalate
FR
methyl 2-hexenoate
FL/FR
6-
methyl-5-hepten-2-one propylene glycol acetal
FL/FR
fermented
3-
methyl-1-pentanol
FL/FR
floral
alpha-
amyl cinnamaldehyde diethyl acetal
FR
bursera graveolens wood oil
FL/FR
citronellal
FL/FR
citronellol
FL/FR
citronellyl acetate
FL/FR
citronellyl butyrate
FL/FR
citronellyl propionate
FL/FR
gamma-
damascone
FR
dihydrocitronellyl ethyl ether
FR
6,8-
dimethyl-2-nonanol
FR
(E)-
geranyl acetone
FL/FR
geranyl tiglate
FL/FR
lily propanol
FR
nerolidol
FL/FR
(E)-
nerolidol
FL/FR
neryl isovalerate
FL/FR
papaya isobutyrate
FL/FR
terpinyl formate
FL/FR
(E)-2,5,9-
trimethyl-4,9-decadien-1-al
FR
fruity
acetaldehyde dihexyl acetal
FL/FR
iso
amyl 2-methyl butyrate
FL/FR
amyl hexanoate
FL/FR
berry pentadienoate
FL/FR
iso
butyl 2-methyl butyrate
FL/FR
ethyl citronellate
FL/FR
ethyl isobutyrate
FL/FR
ethyl methyl-para-tolyl glycidate
FL/FR
geranyl isovalerate
FL/FR
heptanal cyclic ethylene acetal
FR
heptyl isobutyrate
FL/FR
hexanal propylene glycol acetal
FL/FR
(Z)-3-
hexen-1-yl 2-methyl-2-pentenoate
FR
hexyl isovalerate
FL/FR
hexyl propionate
FL/FR
linalyl hexanoate
FL/FR
methyl valerate
FL/FR
4-
phenyl-2-butyl acetate
FL/FR
iso
propyl isobutyrate
FL/FR
tropical specialty
FR
(E)-2-
undecenal
FL/FR
green
acetaldehyde benzyl 2-methoxyethyl acetal
FL/FR
acetaldehyde methyl hexyl acetal
FR
butyl 2-methyl butyrate
FL/FR
citrus carbaldehyde / methyl anthranilate schiff's base
FR
cognac heptanone
FL/FR
ethyl (E)-2-hexenoate
FL/FR
ethyl (E)-4-decenoate
FL/FR
green carboxylate
FR
green dioxolane
FR
(Z)-3-
hexen-1-yl (E)-2-hexenoate
FL/FR
(E)-2-
hexen-1-yl acetate
FL/FR
(Z)-3-
hexen-1-yl acetate
FL/FR
(Z)-3-
hexen-1-yl hexanoate
FL/FR
(Z)-3-
hexen-1-yl isovalerate
FL/FR
(Z)-3-
hexen-1-yl oxyacetaldehyde
FR
(E)-2-
hexen-1-yl propionate
FL/FR
(E)-2-
hexen-1-yl valerate
FL/FR
(Z)-3-
hexen-1-yl valerate
FL/FR
2-
hexenyl acetate
FL/FR
hexyl butyrate
FL/FR
hexyl isobutyrate
FL/FR
3,6-
ivy carbaldehyde
FL/FR
ivy carbaldehyde
FL/FR
2,4-
ivy carbaldehyde
FL/FR
3,5-
ivy carbaldehyde
FL/FR
dextro-
limonene oxide
FL/FR
laevo-
linalyl acetate
FL/FR
dextro-
linalyl acetate
FL/FR
melon heptenal propylene glycol acetal
FL/FR
(2-
methoxy-1-methyl butyl) benzene
FR
octanal diethyl acetal
FL/FR
octanal dimethyl acetal
FL/FR
(E)-2-
octen-1-ol
FL/FR
(E)-2-
pentenal
FL/FR
alpha-iso
propyl phenyl acetaldehyde
FL/FR
sorbyl isobutyrate
FL/FR
thiogeraniol
FL/FR
herbal
2-
dodecenal
FL/FR
linalyl acetate
FL/FR
linalyl formate
FL/FR
6-
methoxy-2,6-dimethyl octanal
FR
(1S,5R)-
myrtenyl acetate
FL/FR
tricyclodecyl acetate
FR
sulfurous
buchu mercaptan
FL/FR
terpenic
alpha-
phellandrene
FL/FR
waxy
decanal dimethyl acetal
FL/FR
3-
decanone
FL/FR
9-
decenoic acid
FL/FR
(E)-
methyl geranate
FL/FR
woody
humulus lupulus extract
FL/FR
woody acetate
FR
For Flavor
No flavor group found for these
acetaldehyde benzyl 2-methoxyethyl acetal
FL/FR
allyl tiglate
FL
bursera graveolens wood oil
FL/FR
butyl 2-methyl butyrate
FL/FR
beta-
cubebene
FL
decanal dimethyl acetal
FL/FR
3-
decanone
FL/FR
(E,E,Z)-2,4,7-
decatrienal
FL
2,4,7-
decatrienal
FL
dihydronootkatone
FL
(Z)-4-
dodecenal
FL/FR
(E,E)-2,4-
heptadien-1-ol
FL
2-
hexenal diethyl acetal
FL
2-
hexenyl acetate
FL/FR
hexyl propionate
FL/FR
ivy carbaldehyde
FL/FR
3,5-
ivy carbaldehyde
FL/FR
(Z)-
linalool oxide (pyranoid)
FL/FR
laevo-
linalyl acetate
FL/FR
dextro-
linalyl acetate
FL/FR
linalyl formate
FL/FR
linalyl hexanoate
FL/FR
melon heptenal propylene glycol acetal
FL/FR
3-
mercaptooctanal
FL
methyl 2-hexenoate
FL/FR
methyl 4-pentenoate
FL
(E)-
methyl geranate
FL/FR
(Z+E)-2-
methyl-2-(4-methyl-3-pentenyl) cyclopropane carbaldehyde
FL/FR
6-
methyl-5-hepten-2-one propylene glycol acetal
FL/FR
4-
phenyl-2-butyl acetate
FL/FR
iso
propyl isobutyrate
FL/FR
alpha-iso
propyl phenyl acetaldehyde
FL/FR
(Z)-8-
tetradecenal
FL/FR
(E)-
tiglaldehyde
FL/FR
dextro-
limonene oxide
FL/FR
sorbyl isobutyrate
FL/FR
aromatic
aromatic
para-
cresyl isobutyrate
FL/FR
berry
heptyl isobutyrate
FL/FR
citrus
citral diethyl acetal
FL/FR
citral dimethyl acetal
FL/FR
cognac heptanone
FL/FR
dehydronootkatone
FL
litsea cubeba fruit oil
FL/FR
1-
methyl-4-methyl ethenyl cyclohexene sulfurized
FL/FR
dusty
ethyl citronellate
FL/FR
earthy
1-
hexen-3-yl acetate
FL
ethereal
ethyl isobutyrate
FL/FR
fatty
2-
dodecanone
FL/FR
2-
dodecenal
FL/FR
ethyl (E)-4-decenoate
FL/FR
(E)-2-
octen-1-ol
FL/FR
floral
citronellal
FL/FR
citronellol
FL/FR
citronellyl acetate
FL/FR
citronellyl propionate
FL/FR
(E)-
geranyl acetone
FL/FR
geranyl tiglate
FL/FR
linalyl acetate
FL/FR
fruity
iso
amyl 2-methyl butyrate
FL/FR
amyl hexanoate
FL/FR
berry pentadienoate
FL/FR
iso
butyl 2-methyl butyrate
FL/FR
citronellyl butyrate
FL/FR
ethyl (E)-2-hexenoate
FL/FR
ethyl methyl-para-tolyl glycidate
FL/FR
3-
heptyl dihydro-5-methyl-2(3H)-furanone
FL/FR
hexanal propylene glycol acetal
FL/FR
(Z)-3-
hexen-1-yl (E)-2-hexenoate
FL/FR
methyl valerate
FL/FR
neryl isovalerate
FL/FR
terpinyl formate
FL/FR
green
acetaldehyde dihexyl acetal
FL/FR
3-
decen-2-one
FL/FR
geranyl isovalerate
FL/FR
(E)-2-
heptenal
FL
(E)-2-
hexen-1-yl acetate
FL/FR
(Z)-3-
hexen-1-yl acetate
FL/FR
(Z)-3-
hexen-1-yl hexanoate
FL/FR
(Z)-3-
hexen-1-yl isovalerate
FL/FR
(E)-2-
hexen-1-yl propionate
FL/FR
(Z)-3-
hexen-1-yl valerate
FL/FR
(E)-2-
hexen-1-yl valerate
FL/FR
(E)-2-
hexenal diethyl acetal
FL
hexyl butyrate
FL/FR
hexyl isobutyrate
FL/FR
hexyl isovalerate
FL/FR
3,6-
ivy carbaldehyde
FL/FR
2,4-
ivy carbaldehyde
FL/FR
methyl heptenone
FL/FR
(E)-
nerolidol
FL/FR
nerolidol
FL/FR
(E,E)-2,6-
nonadienal
FL
nonanal dimethyl acetal
FL/FR
2,4-
octadienal
FL
octanal diethyl acetal
FL/FR
octanal dimethyl acetal
FL/FR
papaya isobutyrate
FL/FR
(E)-2-
pentenal
FL/FR
herbal
green hexanal
FL/FR
minty
thiogeraniol
FL/FR
soapy
dodecanal (aldehyde C-12 lauric)
FL/FR
sour
3-
methyl valeric acid
FL
sulfurous
buchu mercaptan
FL/FR
terpenic
alpha-
phellandrene
FL/FR
waxy
9-
decenoic acid
FL/FR
undecanal
FL/FR
(E)-2-
undecenal
FL/FR
whiskey
3-
methyl-1-pentanol
FL/FR
woody
humulus lupulus extract
FL/FR
(1S,5R)-
myrtenyl acetate
FL/FR
 
Potential Uses:
FLcitrus
 fruit
FLherbal
FLlemon
FLorange
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 acetoacetic acid methyl ester
3-oxobutanoic 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
 

Articles:

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.
PubMed:Reagent assessment for detection of ammonium ion-molecule complexes.
PubMed:Synthesis of small combinatorial libraries of natural products: identification and quantification of new long-chain 3-methyl-2-alkanones from the root essential oil of Inula helenium L. (Asteraceae).
PubMed:E versus Z diazeniumdiolation of acetoacetate-derived carbanions.
PubMed:Reductive whole-cell biotransformation with Corynebacterium glutamicum: improvement of NADPH generation from glucose by a cyclized pentose phosphate pathway using pfkA and gapA deletion mutants.
PubMed:Determination of deoxynivalenol and nivalenol by liquid chromatography and fluorimetric detection with on-line chemical post-column derivatization.
PubMed:[HPLC fingerprint analysis of acetoacetate extraction of Polygonum orientale].
PubMed:Chlorine dioxide-iodide-methyl acetoacetate oscillation reaction investigated by UV-vis and online FTIR spectrophotometric method.
PubMed:Potential hazards to embryo implantation: A human endometrial in vitro model to identify unwanted antigestagenic actions of chemicals.
PubMed:Ionic liquid-based dispersive liquid-liquid microextraction for the determination of formaldehyde in wastewaters and detergents.
PubMed:Dimethyl 4-(4-hy-droxy-phen-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxyl-ate.
PubMed:Engineering yield and rate of reductive biotransformation in Escherichia coli by partial cyclization of the pentose phosphate pathway and PTS-independent glucose transport.
PubMed:A facile four-component sequential protocol in the expedient synthesis of novel 2-aryl-5-methyl-2,3-dihydro-1H-3-pyrazolones in water and their antitubercular evaluation.
PubMed:Electrosynthesis of substituted 1H-indoles from o-nitrostyrenes.
PubMed:Increased NADPH availability in Escherichia coli: improvement of the product per glucose ratio in reductive whole-cell biotransformation.
PubMed:Biomimetic synthesis of hyperolactones.
PubMed:Chiral recognition at one-dimensional metal-organic coordination networks initiates the ordering of prochiral catalytic reagent methylacetoacetate on Au{111}.
PubMed:Enhancement effect of ethyl-2-methyl acetoacetate on triacylglycerols production by a freshwater microalga, Scenedesmus sp. LX1.
PubMed:Propionate analogues of zearalenone bind to Hsp90.
PubMed:Biocatalytic production of (S)-4-bromo-3-hydroxybutyrate and structurally related chemicals and their applications.
PubMed:Effects of a novel allelochemical ethyl 2-methyl acetoacetate (EMA) on the ultrastructure and pigment composition of cyanobacterium Microcystis aeruginosa.
PubMed:Metabolomics for biotransformations: Intracellular redox cofactor analysis and enzyme kinetics offer insight into whole cell processes.
PubMed:Fe(ClO4)3 x 6H2O: a mild and efficient catalyst for one-pot three component synthesis of beta-acetamido carbonyl compounds under solvent-free conditions.
PubMed:(Z)-4-[4-(Dimethyl-amino)benzyl-idene]-3-methyl-isoxazol-5(4H)-one.
PubMed:Tris(methyl 3-oxobutanoato-ÎșO,O')aluminium(III).
PubMed:Lowest transition state for the chirality-determining step in Ru((R)-BINAP)-catalyzed asymmetric hydrogenation of methyl-3-oxobutanoate.
PubMed:Synthesis and biological evaluation of a phosphonate analog of the natural acetyl cholinesterase inhibitor cyclophostin.
PubMed:Investigation of the antioxidant properties of some new 4-hydroxycoumarin derivatives.
PubMed:Engineering of NADPH-dependent aldo-keto reductase from Penicillium citrinum by directed evolution to improve thermostability and enantioselectivity.
PubMed:Development of novel detection reagent for simple and sensitive determination of trace amounts of formaldehyde and its application to flow injection spectrophotometric analysis.
PubMed:[Effects of allelochemical isolated from Phragmites communis on algal membrane permeability].
PubMed:Responses of enzymatic antioxidants and non-enzymatic antioxidants in the cyanobacterium Microcystis aeruginosa to the allelochemical ethyl 2-methyl acetoacetate (EMA) isolated from reed (Phragmites communis).
PubMed:Methyl 2-[(E)-(4-nitro-phen-yl)hydrazono]-3-oxobutyrate.
PubMed:(Z)-Methyl 3-(4-ethoxy-anilino)but-2-enoate.
PubMed:Physiological and biochemical effects of allelochemical ethyl 2-methyl acetoacetate (EMA) on cyanobacterium Microcystis aeruginosa.
PubMed:Pechmann reaction promoted by boron trifluoride dihydrate.
PubMed:[Effects of allelochemical EMA from reed on the production and release of cyanotoxins in Microcystis aeruginosa].
PubMed:Total synthesis of (+)-acutiphycin.
PubMed:[Effects of allelochemical EMA isolated from Phragmites communis on algal cell membrane lipid and ultrastructure].
PubMed:Continuous asymmetric ketone reduction processes with recombinant Escherichia coli.
PubMed:Cyclic and acyclic products from the reactions between methyl 3-oxobutanoate and arylhydrazines.
PubMed:Synthesis, computational study and cytotoxic activity of new 4-hydroxycoumarin derivatives.
PubMed:High production of (2s,3s)-3-hydroxy-2-methylbutanoate by immobilized plant cells of Marchantia polymorpha.
PubMed:Probing the effects of microwave irradiation on enzyme-catalysed organic transformations: the case of lipase-catalysed transesterification reactions.
PubMed:Total synthesis, molecular editing and evaluation of a tripyrrolic natural product: the case of "butylcycloheptylprodigiosin".
PubMed:Dimethyl 4-(4-formyl-phen-yl)-2,6-di-methyl-1,4-dihydro-pyridine-3,5-dicar-boxyl-ate.
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.
PubMed:3,3'-Bis(diphenylphosphino)-1,1'-disubstituted-2,2'-biindoles: easily accessible, electron-rich, chiral diphosphine ligands for homogeneous enantioselective hydrogenation of oxoesters
PubMed:[Reactions of 4,5-dihydro-4-oxo-1H-pyrido(3,2-b)indol-2-carboxylic acid ester].
PubMed:Asymmetric reduction of ethyl 2-methyl e-oxobutanoate by fungi.
PubMed:Asymmetric reduction of ethyl 2-methyl 3-oxobutanoate by Chlorella.
PubMed:Convenient Synthesis of N-Benzyl-1,4-dihydropyridines, Cyclohexenones, and Bicyclo[3.3.1]nonan-3-one Derivatives from 1-Aza-1,3-butadienes.
PubMed:[A new synthesis of 1,4-dihydropyridines: cyclocondensation of aldimines].
PubMed:An improved direct method for the measurement of urinary delta-aminolevulinic acid.
PubMed:Purification and characterization of the NADH-dependent (S)-specific 3-oxobutyryl-CoA reductase from Clostridium tyrobutyricum.
PubMed:A kinetic study and application of a novel carbonyl reductase isolated from Rhodococcus erythropolis.
PubMed:A novel NADH-dependent carbonyl reductase with an extremely broad substrate range from Candida parapsilosis: purification and characterization.
PubMed:Studies of the reductive biotransformation of selected carbonyl compounds by whole cells and extracts of baker's yeast, Saccharomyces carevisiae.
PubMed:Synthesis and biological evaluations of some 2-thioxo-1,2,3,4-tetrahydropyrimidine derivatives.
PubMed:Synthesis and calcium antagonistic activity of some new 2-thioxo-1,2,3,4-tetrahydropyrimidine derivatives.
PubMed:Urinary excretion of 2-methylacetoacetate, 2-methyl-3-hydroxybutyrate and tiglylglycine after isoleucine loading in the diagnosis of 2-methylacetoacetyl-CoA thiolase deficiency.
PubMed:High-performance liquid chromatographic method for determining trichothecene mycotoxins by post-column fluorescence derivatization.
PubMed:High performance liquid chromatographic procedure for quantitative determination of urinary delta-aminolevulinic acid as indices of lead exposure.
PubMed:Hyperketotic states due to inherited defects of ketolysis.
PubMed:[Improved method for the determination of urinary delta-aminolevulinic acid in lead workers].
PubMed:Factors affecting determination of delta-aminolevulinate by use of Ehrlich's reagent.
PubMed:Stimulation of h efflux and inhibition of photosynthesis by esters of carboxylic acids.
PubMed:[Muscle relaxants / 3rd communication: Development of acrylic acid derivatives of potential muscle relaxing activity (author's transl)].
PubMed:Acetoacetyl CoA thiolase deficiency: a cause of severe ketoacidosis in infancy simulating salicylism.
PubMed:Synthesis of eicosa-2-trans-8,11,14-all cis-tetraenoic acid-3-14C and DL-3-hydroxy eicosa-8,11,14-all cis-trienoic acid-3-14C.
 
Notes:
Methylacetoacetic acid has been identified in the urine of patients with an inherited deficiency of propionyl-CoA carboxylase (PMID 630060), and after isoleucine loading in the diagnosis of 2-methylacetoacetyl-CoA thiolase deficiency. (PMID 1861461) [HMDB]
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