Category:cosmetic, flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
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:
Suppliers:
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.
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Hazards identification |
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Classification of the substance or mixture |
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
None found. |
GHS Label elements, including precautionary statements |
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Pictogram | |
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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.
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Dermal Toxicity: |
Not determined
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Inhalation Toxicity: |
Not determined
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Safety in Use Information:
Category: | cosmetic, 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 acetoacetate usage levels up to: | | 2.0000 % in the fragrance concentrate.
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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 |
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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/kg | maximum usage mg/kg |
Dairy products, excluding products of category 02.0 (01.0): | 7.00000 | 35.00000 |
Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 5.00000 | 25.00000 |
Edible ices, including sherbet and sorbet (03.0): | 10.00000 | 50.00000 |
Processed fruit (04.1): | 7.00000 | 35.00000 |
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | - | - |
Confectionery (05.0): | 10.00000 | 50.00000 |
Chewing gum (05.3): | - | - |
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | 5.00000 | 25.00000 |
Bakery wares (07.0): | 10.00000 | 50.00000 |
Meat and meat products, including poultry and game (08.0): | 2.00000 | 10.00000 |
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 2.00000 | 10.00000 |
Eggs and egg products (10.0): | - | - |
Sweeteners, including honey (11.0): | - | - |
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 5.00000 | 25.00000 |
Foodstuffs intended for particular nutritional uses (13.0): | 10.00000 | 50.00000 |
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | 5.00000 | 25.00000 |
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 10.00000 | 50.00000 |
Ready-to-eat savouries (15.0): | 20.00000 | 100.00000 |
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 5.00000 | 25.00000 |
Safety References:
European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...
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European Food Safety Authority (EFSA) reference(s):
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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
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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
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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
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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
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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
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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
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EPI System: View |
NIOSH International Chemical Safety Cards:search |
Chemical Carcinogenesis Research Information System:Search |
AIDS Citations:Search |
Cancer Citations:Search |
Toxicology Citations: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:
Other Information:
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 |
(E)- nerolidol FL/FR |
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 |
butyl 2-methyl butyrate 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 |
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 |
(Z)-3- hexen-1-yl acetate FL/FR |
(E)-2- 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 |
(Z)-3- hexen-1-yl valerate FL/FR |
(E)-2- 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 |
3,5- ivy carbaldehyde FL/FR |
ivy carbaldehyde FL/FR |
2,4- ivy carbaldehyde FL/FR |
dextro- limonene oxide FL/FR |
dextro- linalyl acetate FL/FR |
laevo- 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 |
beta- cubebene FL |
decanal dimethyl acetal FL/FR |
3- decanone FL/FR |
2,4,7- decatrienal FL |
(E,E,Z)-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 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 |
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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 |
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 |
(E)-2- hexen-1-yl valerate FL/FR |
(Z)-3- hexen-1-yl valerate FL/FR |
(E)-2- hexenal diethyl acetal FL |
hexyl butyrate FL/FR |
hexyl isobutyrate FL/FR |
hexyl isovalerate FL/FR |
2,4- ivy carbaldehyde FL/FR |
3,6- ivy carbaldehyde FL/FR |
methyl heptenone FL/FR |
nerolidol FL/FR |
(E)- 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 |
thiogeraniol FL/FR |
herbal |
green hexanal FL/FR |
linalyl formate 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:
Occurrence (nature, food, other): note
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 |
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. |
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