Category: flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
Appearance: | white clear liquid (est) |
Assay: | 98.00 to 100.00 %
|
Food Chemicals Codex Listed: | No |
Melting Point: | 32.00 to 34.00 °C. @ 760.00 mm Hg
|
Boiling Point: | 80.00 to 82.00 °C. @ 16.00 mm Hg
|
Vapor Pressure: | 0.482000 mmHg @ 25.00 °C. (est) |
Flash Point: | 179.00 °F. TCC ( 81.67 °C. )
|
logP (o/w): | -0.731 (est) |
Soluble in: |
| alcohol | | water | | water, 1e+006 mg/L @ 25 °C (est) |
Organoleptic Properties:
|
Odor Type: caramellic |
|
| sweet brown caramellic creamy lactonic |
Odor Description: at 1.00 % in propylene glycol. | sweet brown caramel creamy lactonic |
|
| sweet brown caramellic creamy lactonic |
Odor Description:
| Sweet, brown, caramellic, creamy with lactonic nuances Mosciano, Gerard P&F 18, No. 3, 53, (1993) |
|
|
Flavor Type: brown |
|
| sweet brown creamy caramellic fatty |
Taste Description: at 25.00 ppm. | Sweet, brown, creamy, caramellic with a fatty nuance Mosciano, Gerard P&F 18, No. 3, 53, (1993) |
|
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 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. S 24/25 - Avoid contact with skin and eyes. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 36/37/39 - Wear suitable clothing, 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 | |
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Hazard statement(s) |
None found. |
Precautionary statement(s) |
None found. |
Oral/Parenteral Toxicity: |
Not determined
|
Dermal Toxicity: |
Not determined
|
Inhalation Toxicity: |
Not determined
|
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 |
|
Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.024 (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: 13 |
Click here to view publication 13 |
| average usual ppm | average maximum ppm |
baked goods: | - | 2.00000 |
beverages(nonalcoholic): | - | 1.00000 |
beverages(alcoholic): | - | - |
breakfast cereal: | - | - |
cheese: | - | - |
chewing gum: | - | - |
condiments / relishes: | - | - |
confectionery froastings: | - | - |
egg products: | - | - |
fats / oils: | - | - |
fish products: | - | - |
frozen dairy: | - | 12.00000 |
fruit ices: | - | - |
gelatins / puddings: | - | - |
granulated sugar: | - | - |
gravies: | - | - |
hard candy: | - | - |
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): |
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 |
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 |
EPI System: | View |
AIDS Citations: | Search |
Cancer Citations: | Search |
Toxicology Citations: | Search |
EPA Substance Registry Services (TSCA): | 600-18-0 |
EPA ACToR: | Toxicology Data |
EPA Substance Registry Services (SRS): | Registry |
Laboratory Chemical Safety Summary : | 58 |
National Institute of Allergy and Infectious Diseases: | Data |
WGK Germany: | 3 |
| 2-oxobutanoic acid |
Chemidplus: | 0000600180 |
References:
Other Information:
Potential Blenders and core components note
|
For Odor |
acidic |
acidic |
| cyclohexyl acetic acid | FL/FR |
aldehydic |
| acetyl nonyryl | FL/FR |
balsamic |
2- | acetyl furan | FL/FR |
buttery |
| acetoin | FL/FR |
| acetyl butyryl | FL/FR |
| acetyl isobutyryl | FL/FR |
| acetyl propionyl | FL/FR |
| butyl butyryl lactate | FL/FR |
3,4- | hexane dione | FL/FR |
| caramel pentadione | FL/FR |
| cyclotene | FL/FR |
| cyclotene hydrate | FL/FR |
alpha,alpha- | dimethyl anisyl acetone | FL/FR |
| ethyl 2-hydroxy-2-methyl butyrate | FL/FR |
| ethyl cyclopentenolone | FL/FR |
| ethyl maltol | FL/FR |
5- | ethyl-2,3,4,5-tetramethyl-2-cyclohexen-1-one | FL/FR |
| fenugreek absolute | FL/FR |
| geranyl crotonate | FR |
| immortelle absolute | FL/FR |
| levulinic acid | FL/FR |
| maltol | FL/FR |
| maltyl propionate | FL/FR |
| maple furanone | FL/FR |
| menthone lactone | FL/FR |
| mesitene lactone | FR |
5- | methyl furfural | FL/FR |
| rosefuran | FL/FR |
| shoyu furanone | FL/FR |
| strawberry furanone | FL/FR |
| strawberry furanone acetate | FL/FR |
| toffee furanone | FL/FR |
cheesy |
| butyric acid | FL/FR |
coconut |
| coconut decanone methyl | FR |
delta- | decalactone | FL/FR |
delta-2- | dodecenolactone | FL/FR |
gamma- | heptalactone | FL/FR |
delta- | nonalactone | FL/FR |
gamma- | octalactone | FL/FR |
delta- | undecalactone | FL/FR |
coumarinic |
| phthalide | FL/FR |
| tonka bean resinoid | FR |
creamy |
gamma- | butyrolactone | FL/FR |
| creamy lactone | FL/FR |
3- | heptyl dihydro-5-methyl-2(3H)-furanone | FL/FR |
para- | vanillic acid | FL/FR |
para- | vanillyl alcohol | FL/FR |
earthy |
1- | nonen-3-ol | FL/FR |
ethereal |
| ethyl 4-pentenoate | FL/FR |
| ethyl pyruvate | FL/FR |
iso | valeraldehyde propylene glycol acetal | FL/FR |
fatty |
(Z)- | dairy lactone | FL/FR |
| ethyl undecylenate | FL/FR |
4- | methyl octanoic acid | FL/FR |
fermented |
| butyl laevo-lactate | FL/FR |
| ethyl (E)-2-crotonate | FL/FR |
floral |
iso | jasmone | FL/FR |
| methyl dihydrojasmonate | FL/FR |
fruity |
| acetoin acetate | FL/FR |
gamma- | decalactone | FL/FR |
epsilon- | dodecalactone | FL/FR |
(E)- | ethyl tiglate | FL/FR |
| farnesyl acetone | FL/FR |
| methyl (Z)-5-octenoate | FL/FR |
| tetrahydrofurfuryl acetate | FL/FR |
gamma- | undecalactone (aldehyde C-14 (so-called)) | FL/FR |
green |
iso | amyl 3-(2-furan) propionate | FL/FR |
iso | butyl benzyl carbinol | FL/FR |
| butyl lactate | FL/FR |
(Z)-4- | hepten-1-ol | FL/FR |
(Z)-4- | heptenal | FL/FR |
(Z)-4- | heptenal diethyl acetal | FL/FR |
2- | heptyl furan | FL/FR |
herbal |
| butyl levulinate | FL/FR |
mushroom |
3- | octen-2-ol | FL/FR |
musty |
3- | acetyl-2,5-dimethyl furan | FL/FR |
nutty |
2- | acetyl-3,5(or 6)-dimethyl pyrazine | FL/FR |
2,3- | dimethyl pyrazine | FL/FR |
| nutty cyclohexenone | FL/FR |
phenolic |
4- | methyl-2,6-dimethoxyphenol | FL/FR |
(E)- | coconut decanone ethyl | FR |
(E)- | tiglic acid | FL/FR |
sweet |
| vanilla oleoresin bali | FL/FR |
tonka |
6- | amyl-alpha-pyrone | FL/FR |
| mint lactone | FL/FR |
| octahydrocoumarin | FL/FR |
| tonka bean absolute | FR |
vanilla |
ortho- | dimethyl hydroquinone | FL/FR |
| ethyl vanillin | FL/FR |
| ethyl vanillin isobutyrate | FL/FR |
| ethyl vanillin propylene glycol acetal | FL/FR |
| vanillin | FL/FR |
| vanillyl acetate | FL/FR |
| vanillyl isobutyrate | FL/FR |
| vanillylidene acetone | FL/FR |
vegetable |
| methional | FL/FR |
| tetrahydrofurfuryl alcohol | FL/FR |
waxy |
| allyl nonanoate | FL/FR |
| ethyl palmitate | FL/FR |
| methyl laurate | FL/FR |
2- | nonanol | FL/FR |
| octyl 2-methyl butyrate | FL/FR |
| octyl isobutyrate | FL/FR |
delta- | tetradecalactone | FL/FR |
| undecanoic acid | FL/FR |
|
For Flavor |
|
No flavor group found for these |
2- | acetyl-3,4,5,6-tetrahydropyridine | FL |
| allyl 2-furoate | FL |
| allyl methyl trisulfide | FL |
| benzyl disulfide | FL |
6- | decenoic acid | FL |
2,5- | diethyl tetrahydrofuran | FL |
alpha,alpha- | dimethyl anisyl acetone | FL/FR |
ortho- | dimethyl hydroquinone | FL/FR |
epsilon- | dodecalactone | FL/FR |
delta-2- | dodecenolactone | FL/FR |
| ethyl 2-hydroxy-2-methyl butyrate | FL/FR |
| ethyl 4-pentenoate | FL/FR |
5- | ethyl-2,3,4,5-tetramethyl-2-cyclohexen-1-one | FL/FR |
| farnesyl acetone | FL/FR |
| furfuryl acetone | FL |
| menthone lactone | FL/FR |
| rosefuran | FL/FR |
(R)- | tonka furanone | FL |
|
iso | amyl 3-(2-furan) propionate | FL/FR |
acidic |
| levulinic acid | FL/FR |
dextro,laevo- | tartaric acid | FL |
aldehydic |
| acetyl nonyryl | FL/FR |
amber |
iso | butyl benzyl carbinol | FL/FR |
balsamic |
| vanillylidene acetone | FL/FR |
bready |
| mango furanone | FL |
brown |
5- | methyl furfural | FL/FR |
| tetrahydrofurfuryl acetate | FL/FR |
(E)- | tiglic acid | FL/FR |
burnt |
| furfuryl alcohol | FL |
buttery |
| butyl laevo-lactate | FL/FR |
| diacetyl | FL |
3,4- | hexane dione | FL/FR |
cabbage |
| methyl 2-thiofuroate | FL |
caramellic |
| caramel dione | FL |
| caramel furanone | FL |
| caramel malted mambo flavor | FL |
| caramel pentadione | FL/FR |
| creme brulee flavor | FL |
| cyclotene | FL/FR |
| cyclotene hydrate | FL/FR |
| ethyl maltol | FL/FR |
5- | ethyl-3,4,5,6-tetramethyl cyclohexen-2-one | FL |
| fenugreek absolute | FL/FR |
barley | malt extract | FL |
| maltol | FL/FR |
| maltyl propionate | FL/FR |
| maple cream flavor | FL |
| maple furanone | FL/FR |
3- | methyl butyl 2-furyl butyrate | FL |
| shoyu furanone | FL/FR |
| strawberry furanone | FL/FR |
| strawberry furanone acetate | FL/FR |
| toffee furanone | FL/FR |
coconut |
delta- | decalactone | FL/FR |
(R)- | massoia lactone | FL |
6- | methyl coumarin | FL |
| octahydrocoumarin | FL/FR |
coffee |
| coffee creme brulee flavor | FL |
2- | thiophene thiol | FL |
coumarinic |
| phthalide | FL/FR |
creamy |
| acetoin | FL/FR |
| acetyl butyryl | FL/FR |
| acetyl isobutyryl | FL/FR |
6- | amyl-alpha-pyrone | FL/FR |
| butyl butyryl lactate | FL/FR |
| creamy lactone | FL/FR |
| mint lactone | FL/FR |
delta- | nonalactone | FL/FR |
| octyl isobutyrate | FL/FR |
delta- | undecalactone | FL/FR |
gamma- | undecalactone (aldehyde C-14 (so-called)) | FL/FR |
para- | vanillic acid | FL/FR |
para- | vanillyl alcohol | FL/FR |
dairy |
| creme brulle coffee flavor | FL |
| methyl (Z)-5-octenoate | FL/FR |
earthy |
1- | nonen-3-ol | FL/FR |
eggy |
| egg nog creme brulee flavor | FL |
fatty |
(Z)- | dairy lactone | FL/FR |
| ethyl undecylenate | FL/FR |
2- | heptyl furan | FL/FR |
4- | methyl octanoic acid | FL/FR |
2,4- | octadien-1-ol | FL |
(E,E)-2,4- | undecadienal | FL |
2,4- | undecadienal | FL |
floral |
| methyl dihydrojasmonate | FL/FR |
fruity |
| acetoin acetate | FL/FR |
| acetyl isovaleryl | FL |
gamma- | decalactone | FL/FR |
(E)- | ethyl tiglate | FL/FR |
| furfuryl valerate | FL |
3- | heptyl dihydro-5-methyl-2(3H)-furanone | FL/FR |
2- | pentanoyl furan | FL |
iso | valeraldehyde propylene glycol acetal | FL/FR |
green |
| butyl lactate | FL/FR |
| heptanal 2,3-butane diol acetal | FL |
(Z)-4- | hepten-1-ol | FL/FR |
(Z)-4- | heptenal | FL/FR |
(Z)-4- | heptenal diethyl acetal | FL/FR |
| immortelle absolute | FL/FR |
iso | jasmone | FL/FR |
herbal |
| butyl levulinate | FL/FR |
5- | hydroxymethyl furfural | FL |
| massoia bark oil | FL |
jammy |
| ethyl cyclopentenolone | FL/FR |
lactonic |
gamma- | heptalactone | FL/FR |
gamma- | octalactone | FL/FR |
milky |
gamma- | butyrolactone | FL/FR |
mushroom |
3- | octen-2-ol | FL/FR |
musty |
| ethyl (E)-2-crotonate | FL/FR |
nutty |
2- | acetyl furan | FL/FR |
3- | acetyl-2,5-dimethyl furan | FL/FR |
2- | acetyl-3,5(or 6)-dimethyl pyrazine | FL/FR |
2,3- | dimethyl pyrazine | FL/FR |
| nutty cyclohexenone | FL/FR |
| peanut oxazole | FL |
| tetrahydrofurfuryl alcohol | FL/FR |
phenolic |
4- | methyl-2,6-dimethoxyphenol | FL/FR |
rummy |
| ethyl pyruvate | FL/FR |
sour |
| butyric acid | FL/FR |
spicy |
| benzylidene acetone | FL |
sweet |
| cyclohexyl acetic acid | FL/FR |
dextro- | sorbitol | FL |
| vanilla oleoresin bali | FL/FR |
toasted |
| acetyl propionyl | FL/FR |
tomato |
| methional | FL/FR |
vanilla |
| ethyl vanillin | FL/FR |
| ethyl vanillin isobutyrate | FL/FR |
| ethyl vanillin propylene glycol acetal | FL/FR |
| vanillin | FL/FR |
| vanillyl acetate | FL/FR |
| vanillyl isobutyrate | FL/FR |
waxy |
| allyl nonanoate | FL/FR |
| ethyl palmitate | FL/FR |
| furfuryl octanoate | FL |
| methyl laurate | FL/FR |
2- | nonanol | FL/FR |
| octyl 2-furoate | FL |
| octyl 2-methyl butyrate | FL/FR |
delta- | tetradecalactone | FL/FR |
| undecanoic acid | FL/FR |
|
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
2-keto | butanoic acid | 2-oxo | butanoic acid | 2-oxo- | butanoic acid | | butanoic acid, 2-oxo- | a-keto | butric acid | 2-keto | butyric acid | 2-keto-N- | butyric acid | 2-oxo- | butyric acid | 2-oxo-n- | butyric acid | a-keto | butyric acid | a-keto-n- | butyric acid | a-oxo | butyric acid | a-oxo-n- | butyric acid | alpha-keto | butyric acid | alpha-oxo-N- | butyric acid | | butyric acid, 2-oxo- | 2-oxo | butyricacid | a-keto | butyricacid | | formic acid, propionyl- | 3- | methyl pyruvic acid | | methyl-pyruvic acid | 3- | methylpyruvic acid | | propionyl formic acid | | propionylformic acid | | pyruvic acid, methyl- |
Articles:
PubMed: | [Screening and identification of an endophytic bacterium with 1-aminocyclopropane-1-carboxylate deaminase activity from Panax ginseng and its effect on host growth]. |
PubMed: | Gordonibacter urolithinfaciens sp. nov., a urolithin-producing bacterium isolated from the human gut. |
PubMed: | Crystal structures of human CtBP in complex with substrate MTOB reveal active site features useful for inhibitor design. |
PubMed: | A QM/MM study on the reaction pathway leading to 2-aceto-2-hydroxybutyrate in the catalytic cycle of AHAS. |
PubMed: | Molecular evolution of threonine dehydratase in bacteria. |
PubMed: | A one-pot system for production of L-2-aminobutyric acid from L-threonine by L-threonine deaminase and a NADH-regeneration system based on L-leucine dehydrogenase and formate dehydrogenase. |
PubMed: | Highly stereoselective biosynthesis of (R)-α-hydroxy carboxylic acids through rationally re-designed mutation of D-lactate dehydrogenase. |
PubMed: | Conserved pyridoxal protein that regulates Ile and Val metabolism. |
PubMed: | Effect of amino acids on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in creatinine/phenylalanine and creatinine/phenylalanine/4-oxo-2-nonenal reaction mixtures. |
PubMed: | C-terminal binding proteins are essential pro-survival factors that undergo caspase-dependent downregulation during neuronal apoptosis. |
PubMed: | Enhancing (L)-isoleucine production by thrABC overexpression combined with alaT deletion in Corynebacterium glutamicum. |
PubMed: | BRCA1 expression is epigenetically repressed in sporadic ovarian cancer cells by overexpression of C-terminal binding protein 2. |
PubMed: | Determination of α-keto acids in pork meat and Iberian ham via tandem mass spectrometry. |
PubMed: | Synergy as design principle for metabolic engineering of 1-propanol production in Escherichia coli. |
PubMed: | Microbial Community-Level Physiological Profiles (CLPP) and herbicide mineralization potential in groundwater affected by agricultural land use. |
PubMed: | Efficient bioconversion of l-threonine to 2-oxobutyrate using whole cells of Pseudomonas stutzeri SDM. |
PubMed: | Isolation of Rhizobacteria from Jatropha curcas and characterization of produced ACC deaminase. |
PubMed: | Variability of Escherichia coli O157 strain survival in manure-amended soil in relation to strain origin, virulence profile, and carbon nutrition profile. |
PubMed: | Effects of gamma-ray-induced free radicals on the metal content and amino acid composition of human metallothionein-1. |
PubMed: | Asymmetric formal [3+2] cycloaddition reaction of isocyanoesters to 2-oxobutenoate esters by a multifunctional chiral silver catalyst. |
PubMed: | Kinetic resolution of 2-hydroxybutanoate racemic mixtures by NAD-independent L-lactate dehydrogenase. |
PubMed: | Mechanistic studies of 1-aminocyclopropane-1-carboxylate deaminase: characterization of an unusual pyridoxal 5'-phosphate-dependent reaction. |
PubMed: | Biosynthesis of chiral 3-hydroxyvalerate from single propionate-unrelated carbon sources in metabolically engineered E. coli. |
PubMed: | Three-component assembly and divergent ring-expansion cascades of functionalized 2-iminooxetanes. |
PubMed: | Therapeutic targeting of C-terminal binding protein in human cancer. |
PubMed: | Cloning and characterisation of a cystathionine β/γ-lyase from two Oenococcus oeni oenological strains. |
PubMed: | Exploring methionine γ-lyase structure-function relationship via microspectrophotometry and X-ray crystallography. |
PubMed: | Expanding metabolism for total biosynthesis of the nonnatural amino acid L-homoalanine. |
PubMed: | Characterization of ACC deaminase gene in Pseudomonas entomophila strain PS-PJH isolated from the rhizosphere soil. |
PubMed: | Efficient production of 2-oxobutyrate from 2-hydroxybutyrate by using whole cells of Pseudomonas stutzeri strain SDM. |
PubMed: | Site-directed mutagenesis on human cystathionine-gamma-lyase reveals insights into the modulation of H2S production. |
PubMed: | Transaminase-catalyzed asymmetric synthesis of L-2-aminobutyric acid from achiral reactants. |
PubMed: | Acetohydroxyacid synthase, a novel target for improvement of L-lysine production by Corynebacterium glutamicum. |
PubMed: | Directed evolution of Methanococcus jannaschii citramalate synthase for biosynthesis of 1-propanol and 1-butanol by Escherichia coli. |
PubMed: | Identification of a methioninase inhibitor, myrsinoic acid B, from Myrsine seguinii Lév., and its inhibitory activities. |
PubMed: | Direct methods and residue type specific isotope labeling in NMR structure determination and model-driven sequential assignment. |
PubMed: | Isothermal titration microcalorimetry reveals the cooperative and noncompetitive nature of inhibition of Sinorhizobium meliloti L5-30 dihydrodipicolinate synthase by (S)-lysine. |
PubMed: | [Overproduction of noncanonical amino acids by Escherichia coli cells]. |
PubMed: | Elucidation of an alternate isoleucine biosynthesis pathway in Geobacter sulfurreducens. |
PubMed: | Production of the apoptotic cellular mediator 4-Methylthio-2-oxobutyric acid by using an enzymatic stirred tank reactor with in situ product removal. |
PubMed: | SanM catalyzes the formation of 4-pyridyl-2-oxo-4-hydroxyisovalerate in nikkomycin biosynthesis by interacting with SanN. |
PubMed: | Perspectives of bacterial ACC deaminase in phytoremediation. |
PubMed: | A novel strategy for enzymatic synthesis of 4-hydroxyisoleucine: identification of an enzyme possessing HMKP (4-hydroxy-3-methyl-2-keto-pentanoate) aldolase activity. |
PubMed: | The crystal structure of Escherichia coli TdcF, a member of the highly conserved YjgF/YER057c/UK114 family. |
PubMed: | Bacillus decisifrondis sp. nov., isolated from soil underlying decaying leaf foliage. |
PubMed: | Enzymology and evolution of the pyruvate pathway to 2-oxobutyrate in Methanocaldococcus jannaschii. |
PubMed: | Silencing threonine deaminase and JAR4 in Nicotiana attenuata impairs jasmonic acid-isoleucine-mediated defenses against Manduca sexta. |
PubMed: | Evidence for distinct L-methionine catabolic pathways in the yeast Geotrichum candidum and the bacterium Brevibacterium linens. |
PubMed: | Accumulation of homolanthionine and activation of a novel pathway for isoleucine biosynthesis in Corynebacterium glutamicum McbR deletion strains. |
PubMed: | Functional analysis of all aminotransferase proteins inferred from the genome sequence of Corynebacterium glutamicum. |
PubMed: | Crystallization and some properties of D-lactate dehydrogenase from Staphylococcus sp. LDH-1. |
PubMed: | Involvement of a branched-chain aminotransferase in production of volatile sulfur compounds in Yarrowia lipolytica. |
PubMed: | The mitochondrial branched-chain aminotransferase (AtBCAT-1) is capable to initiate degradation of leucine, isoleucine and valine in almost all tissues in Arabidopsis thaliana. |
PubMed: | Structural analysis of Pseudomonas 1-aminocyclopropane-1-carboxylate deaminase complexes: insight into the mechanism of a unique pyridoxal-5'-phosphate dependent cyclopropane ring-opening reaction. |
PubMed: | Transcarboxylase 5S structures: assembly and catalytic mechanism of a multienzyme complex subunit. |
PubMed: | Assay method for antitumor L-methionine gamma-lyase: comprehensive kinetic analysis of the complex reaction with L-methionine. |
PubMed: | Role of a conserved arginine in the mechanism of acetohydroxyacid synthase: catalysis of condensation with a specific ketoacid substrate. |
PubMed: | Reduced transaminase B (IlvE) activity caused by the lack of yjgF is dependent on the status of threonine deaminase (IlvA) in Salmonella enterica serovar Typhimurium. |
PubMed: | Effect of alpha-ketobutyrate on microvascular thickness in the diabetic rat kidney. |
PubMed: | Catabolism of volatile sulfur compounds precursors by Brevibacterium linens and Geotrichum candidum, two microorganisms of the cheese ecosystem. |
PubMed: | Detection of carboxylic acids and inhibition of hippuric acid formation in rats treated with 3-butene-1,2-diol, a major metabolite of 1,3-butadiene. |
PubMed: | Dual influence of the carbon source and L-methionine on the synthesis of sulphur compounds in the cheese-ripening yeast Geotrichum candidum. |
PubMed: | A sensitive and robust method for obtaining intermolecular NOEs between side chains in large protein complexes. |
PubMed: | Reaction of 1-amino-2-methylenecyclopropane-1-carboxylate with 1-aminocyclopropane-1-carboxylate deaminase: analysis and mechanistic implications. |
PubMed: | Amino acid catabolism and generation of volatiles by lactic acid bacteria. |
PubMed: | Substrate recognition by 2-oxoacid:ferredoxin oxidoreductase from Sulfolobus sp. strain 7. |
PubMed: | Synthesis of labeled 1-amino-2-methylenecyclopropane-1-carboxylic acid, an inactivator of 1-aminocyclopropane-1-carboxylate deaminase. |
PubMed: | Sulfur compound production by Geotrichum candidum from L-methionine: importance of the transamination step. |
PubMed: | Contribution of enzymic alpha, gamma-elimination reaction in detoxification pathway of selenomethionine in mouse liver. |
PubMed: | The large scale synthesis of "unnatural" amino acids. |
PubMed: | Conversion of Escherichia coli pyruvate oxidase to an 'alpha-ketobutyrate oxidase'. |
PubMed: | Biochemical and molecular characterization of taurine:pyruvate aminotransferase from the anaerobe Bilophila wadsworthia. |
PubMed: | L-Vinylglycine is an alternative substrate as well as a mechanism-based inhibitor of 1-aminocyclopropane-1-carboxylate synthase. |
PubMed: | Metabolic and K(ATP) channel-independent actions of keto acid initiators of insulin secretion. |
PubMed: | Engineering of a novel biochemical pathway for the biosynthesis of L-2-aminobutyric acid in Escherichia coli K12. |
PubMed: | Artefactual pyruvate and 2-oxobutyrate produced by trimethylsilylation of methylmalonic and ethylmalonic acids in the presence of oxygen. |
PubMed: | Metabolic engineering of Arabidopsis and Brassica for poly(3-hydroxybutyrate-co-3-hydroxyvalerate) copolymer production. |
PubMed: | Description of Cellulophaga baltica gen. nov., sp. nov. and Cellulophaga fucicola gen. nov., sp. nov. and reclassification of [Cytophaga] lytica to Cellulophaga lytica gen. nov., comb. nov. |
PubMed: | Use of 13C nuclear magnetic resonance and gas chromatography to examine methionine catabolism by lactococci. |
PubMed: | Substrate selectivity and biochemical properties of 4-hydroxy-2-keto-pentanoic acid aldolase from Escherichia coli. |
PubMed: | Pyruvate protects neurons against hydrogen peroxide-induced toxicity. |
PubMed: | Active site plasticity in D-amino acid oxidase: a crystallographic analysis. |
PubMed: | Oocyte and zygote ketoaldehyde utilisation. |
PubMed: | High resolution 1H NMR investigations of the reactivities of alpha-keto acid anions with hydrogen peroxide. |
PubMed: | Production of heteropolymeric polyhydroxyalkanoate in Escherichia coli from a single carbon source. |
PubMed: | Determination of short-chain aliphatic, oxo- and hydroxy-acids in drinking water at low microgram per liter concentrations. |
PubMed: | Metabolic effects of inhibitors of two enzymes of the branched-chain amino acid pathway in Salmonella typhimurium. |
PubMed: | The effect of three alpha-keto acids on 3-mercaptopyruvate sulfurtransferase activity. |
PubMed: | In vivo threonine oxidation rate is dependent on threonine dietary supply in growing pigs fed low to adequate levels. |
PubMed: | A spectrophotometric determination of alpha-dicarbonyl compounds and its application to the enzymatic formation of alpha-ketobutyrate. |
PubMed: | Channeling behavior and activity models for Escherichia coli K-12 acetohydroxy acid synthases at physiological substrate levels. |
PubMed: | Threonine dehydratases of Corynebacterium glutamicum with altered allosteric control: their generation and biochemical and structural analysis. |
PubMed: | Methionine transamination--metabolic function and subcellular compartmentation. |
PubMed: | Threonine 246 at the active site of the L-lactate dehydrogenase of Bacillus stearothermophilus is important for catalysis but not for substrate binding. |
PubMed: | The oxygenase reaction of acetolactate synthase. |
PubMed: | Cofactor identification of threonine-serine dehydratase from sheep liver. |
PubMed: | Acetohydroxy acid synthase and threonine deaminase activities, and the biosynthesis of isoleucine-leucine-valine in Streptococcus bovis. |
PubMed: | Alpha-keto acids are novel siderophores in the genera Proteus, Providencia, and Morganella and are produced by amino acid deaminases. |
PubMed: | A mechanism for valine-resistant growth of Escherichia coli K-12 supported by the valine-sensitive acetohydroxy acid synthase IV activity from ilvJ662. |
PubMed: | Eurystatins A and B, new prolyl endopeptidase inhibitors. II. Physico-chemical properties and structure determination. |
PubMed: | In vivo nephrotoxic action of an isomeric mixture of S-(1-phenyl-2-hydroxyethyl)glutathione and S-(2-phenyl-2-hydroxyethyl)glutathione in Fischer-344 rats. |
PubMed: | Physiological implications of the substrate specificities of acetohydroxy acid synthases from varied organisms. |
PubMed: | Leaky pantothenate and thiamin mutations of Salmonella typhimurium conferring suphometuron methyl sensitivity. |
PubMed: | Pleiotropic effects of poxA regulatory mutations of Escherichia coli and Salmonella typhimurium, mutations conferring sulfometuron methyl and alpha-ketobutyrate hypersensitivity. |
PubMed: | Effects of alpha-ketobutyrate and alpha-hydroxybutyrate on the enzymatic determination of acetoacetate and beta-hydroxybutyrate. |
PubMed: | Physiological implications of the specificity of acetohydroxy acid synthase isozymes of enteric bacteria. |
PubMed: | Involvement of ack-pta operon products in alpha-ketobutyrate metabolism by Salmonella typhimurium. |
PubMed: | Toxic accumulation of alpha-ketobutyrate caused by inhibition of the branched-chain amino acid biosynthetic enzyme acetolactate synthase in Salmonella typhimurium. |
PubMed: | A method for simultaneous determination of the two possible products of acetohydroxy acid synthase. |
PubMed: | Methionine metabolism in isolated perfused livers from rats fed on zinc-deficient and restricted diets. |
PubMed: | Effect of alpha-ketobutyrate on palmitic acid and pyruvate metabolism in isolated rat hepatocytes. |
PubMed: | Effects of organic acids on the synthesis of citrulline by intact rat liver mitochondria. |
PubMed: | The occurrence of 4-methylthio-2-hydroxybutyrate in human urine. |
PubMed: | Sensitivity of a Salmonella typhimurium aspC mutant to sulfometuron methyl, a potent inhibitor of acetolactate synthase II. |
PubMed: | High performance liquid chromatography determination of cystathionase activity in human and rabbit lenses. |
PubMed: | p-Cresol formation by cell-free extracts of Clostridium difficile. |
PubMed: | alpha-Ketobutyrate metabolism in perfused rat liver: regulation of alpha-ketobutyrate decarboxylation and effects of alpha-ketobutyrate on pyruvate dehydrogenase. |
PubMed: | Directed biosynthesis of paulomycin A. The effect of L-methionine, L-threonine and alpha-ketobutyric acid. |
PubMed: | Heat-shock treatment lethal for mammalian cells deprived of glucose and glutamine: protection by alpha-keto acids. |
PubMed: | Biochemical oxygen activation as the basis for the physiological action of tetrachlorodecaoxide (TCDO). |
PubMed: | Defect in alpha-ketobutyrate metabolism: a new inborn error. |
PubMed: | [Kinetics of uptake of Pherajod by the rabbit eye]. |
PubMed: | Biochemical model reactions for cataract research. |
PubMed: | [The uptake of potassium iodide and its effect as an antioxidant in isolated rabbit eyes]. |
PubMed: | In vivo study of LDH isoenzyme activities in heart, liver and testis cytosols of gossypol-treated rats. |
PubMed: | Synthesis of the isoleucyl- and valyl-tRNA synthetases and the isoleucine-valine biosynthetic enzymes in a threonine deaminase regulatory mutant of Escherichia coli K-12. |
PubMed: | Characterization of alpha-ketobutyrate metabolism in rat tissues: effects of dietary protein and fasting. |
PubMed: | Transaminase inhibitors block glycolysis and G1 to S phase progression in chick embryo fibroblasts: reversal by alpha-keto acids. |
PubMed: | Metabolic alterations mediated by 2-ketobutyrate in Escherichia coli K12. |
PubMed: | Role of 2-ketobutyrate as an alarmone in E. coli K12: inhibition of adenylate cyclase activity mediated by the phosphoenolpyruvate: glycose phosphotransferase transport system. |
PubMed: | Mycoplanecins, novel antimycobacterial antibiotics from Actinoplanes awajinensis subsp. mycoplanecinus subsp. nov. III. Structural determination of mycoplanecin A. |
PubMed: | The structure of the abortive nicotinamide adenine dinucleotide-pyruvate-lactate dehydrogenase complex as determined by circular dichroism. |
PubMed: | 2-Ketobutyrate: a putative alarmone of Escherichia coli. |
PubMed: | Metabolic basis for the isoleucine, pantothenate or methionine requirement of ilvG strains of Salmonella typhimurium. |
PubMed: | Effect of pyruvate and its analogs on the thiamine pyrophosphate binding in the active center of muscle pyruvate dehydrogenase. |
PubMed: | Acetohydroxy acid synthase isoenzymes of Escherichia coli K12 and Salmonella typhimurium. |
PubMed: | Mechanistic studies on the pyridoxal phosphate enzyme 1-aminocyclopropane-1-carboxylate deaminase from Pseudomonas sp. |
PubMed: | Conversion of alpha-ketobutyrate to alpha-amino-n-butyric acid by isolated rat liver cells: effect of ethanol. |
PubMed: | A role for threonine deaminase in the regulation of alpha-acetolactate biosynthesis in Escherichia coli K12. |
PubMed: | Properties of alpha-hydroxyacid dehydrogenase isozymes from Trypanosoma cruzi. |
PubMed: | Decrease of intracellular cystine content in cystinotic fibroblasts by inhibitors of gamma-glutamyl transpeptidase. |
PubMed: | [Estimation of serine- and threonine dehydratase activity of blood serum]. |
PubMed: | A sensitive determination of alpha-keto acids by gas-liquid chromatography and its application to the assay of L-glutamate dehydrogenase and aminotransferases. |
PubMed: | Hydroxyamino acid utilization and alpha-ketobutyrate toxicity in Pseudomonas cepacia. |
PubMed: | Substrate channeling: alpha-ketobutyrate inhibition of acetohydroxy acid synthase in Salmonella typhimurium. |
PubMed: | Beta-hydroxy-alpha-ketobutyric acid in Drosophila melanogaster, with reference to biosynthesis of drosopterins. |
PubMed: | Stereochemistry of the conversions of L-threonine and D-threonine into 2-oxobutanoate by the L-threonine and D-threonine dehydratases of Serratia marcescens. |
PubMed: | Serine sensitivity of Escherichia coli K 12: partial characterization of a serine resistnat mutant that is extremely sensitive to 2-ketobutyrate. |
PubMed: | [Oxidative deamination of beta-methylaspartic acid]. |
PubMed: | Inactivation of the pyruvate dehydrogenase component from pigeon breast muscle pyruvate dehydrogenase complex by alpha-ketobutyric acid. |
PubMed: | Methionine degradation by Pseudomonas fluorescens UK1 and its methionine-utilizing mutant. |
PubMed: | High-speed liquid chromatographic determination of phenylpyruvic acid. |
PubMed: | Sheep liver serine-threonine dehydratase. I. Purification and evidence for covalently linked alpha-ketobutyrate as its cofactor. |
PubMed: | The formation of 2-hydroxybutyric acid in experimental animals. |
PubMed: | beta-Decarboxylation of L-aspartic acid: a metal chelate-catalyzed reaction. |
PubMed: | Neuropharmacological comparison of cystathionine, cysteine, homoserine and alpha-ketobutyric acid in cats. |
PubMed: | A comparative study of the ability of methionine or linolenic acid to act as precursors of ethylene in plant tissues. |
PubMed: | Biosynthesis of ethylene. 4-methylmercapto-2-oxobutyric acid: an intermediate in the formation from methionine. |
PubMed: | On the mechanism of sensitivity to leucine in the case of "leucine sensitive hypoglycemia". II. The hypoglycemic affect of alpha-ketobutyric acid in the case of "leucine sensitive hypoglycemia". |
PubMed: | 2-Oxobutyric acid: effects of its condensation products on lactate dehydrogenase activity. |
PubMed: | Effect of alpha-ketobutyric acid on exytetracycline production in serine-containing medium. |
PubMed: | Alpha-keto acids in vitamin-free casein hydrolyzates (acid). |
PubMed: | Effects of certain thiamine analogs on the enzymatic decarboxylation of alpha-ketobutyric acid. |
PubMed: | alpha-Ketobutyric acid as a product in the enzymatic cleavage of cystathionine. |
PubMed: | Pyruvate oxidation in brain: Evidence derived from the metabolism of alpha-ketobutyric acid. |
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