phenyl pyruvic acid
2-oxo-3-phenylpropionic acid
Identification
| Name | phenyl pyruvic acid |
| IUPAC | 2-oxo-3-phenylpropanoic acid |
| CAS Number | 156-06-9 |
| EINECS | 205-847-1 |
| FDA UNII | X7CO62M413 |
| Molecular Formula | C9 H8 O3 |
| Molecular Weight | 164.16036000 |
| MDL Number | MFCD00002589 |
| Nikkaji Number | J11.025F |
| Beilstein | 2207312 |
| CoE Number | 8109 |
Regulatory
| JECFA Food Flavoring | 1478 2-oxo-3-phenylpropionic acid |
| DG SANTE Food Flavourings | 08.109 3-phenylpyruvic acid |
| FEMA Number | 3892 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 156-06-9 ; 2-OXO-3-PHENYLPROPIONIC ACID |
Physical Properties
| Appearance | pale yellow powder (est) |
| Assay | 98.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 150.00 °C. @ 760.00 mm Hg |
| Boiling Point | 299.00 to 300.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.001000 mmHg @ 25.00 °C. (est) |
| Flash Point | > 212.00 °F. TCC ( > 100.00 °C. ) |
| logP (o/w) | 0.142 (est) |
| Soluble in | alcohol |
Organoleptic Properties
| Odor Strength | medium , |
| Substantivity | 146 hour(s) at 1.00 % in propylene glycol |
| Odor Description | at 100.00 %. |
| Odor sample from | Sigma-Aldrich, Inc.: Aldrich |
| Taste Description | at 80.00 ppm in water. |
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| Recommendation for phenyl pyruvic acid usage levels up to | 0.5000 % in the fragrance concentrate. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | ND (μg/capita/day) |
| Maximised Survey-derived Daily Intakes (MSDI-USA) | 0.09 (μg/capita/day) |
| baked goods | - |
| beverages(nonalcoholic) | 0.50000 |
| beverages(alcoholic) | - |
| breakfast cereal | 1.00000 |
| cheese | 0.50000 |
| chewing gum | 1.00000 |
| condiments / relishes | - |
| confectionery froastings | 1.00000 |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | - |
| fruit ices | 0.50000 |
| gelatins / puddings | 0.50000 |
| granulated sugar | - |
| gravies | - |
| hard candy | 1.00000 |
| imitation dairy | - |
| instant coffee / tea | - |
| jams / jellies | - |
| meat products | - |
| milk products | 0.50000 |
| nut products | - |
| other grains | 1.00000 |
| poultry | - |
| processed fruits | 0.10000 |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | 50.00000 |
| snack foods | - |
| soft candy | 1.00000 |
| soups | - |
| sugar substitutes | 0.50000 |
| sweet sauces | 1.00000 |
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Potential Uses
Natural Occurrence
Synonyms
alpha-oxo-
benzene propanoic acid
alpha-oxo-
benzenepropanoic acid
2-oxo-3-
phenyl propanoic acid
3-
phenyl-2-oxopropanoic acid
2-oxo-3-
phenylpropanic acid
2-oxo-3-
phenylpropanoic acid
2-oxo-3-
phenylpropionic acid
phenylpyruvic acid
3-
phenylpyruvic acid
b-
phenylpyruvic acid
3-
phenylpyruvicacid
PubMed:
Modeling of the total antioxidant capacity of rooibos (Aspalathus linearis) tea infusions from chromatographic fingerprints and identification of potential antioxidant markers.
PubMed:
Production of natural antimicrobial compound D-phenyllactic acid using Leuconostoc mesenteroides ATCC 8293 whole cells involving highly active D-lactate dehydrogenase.
PubMed:
Screening of phenylpyruvic acid producers and optimization of culture conditions in bench scale bioreactors.
PubMed:
Enzymatic production of D-3-phenyllactic acid by Pediococcus pentosaceus D-lactate dehydrogenase with NADH regeneration by Ogataea parapolymorpha formate dehydrogenase.
PubMed:
Effects of fermented rooibos (Aspalathus linearis) on adipocyte differentiation.
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:
Z-2-(β-D-glucopyranosyloxy)-3-phenylpropenoic acid, an α-hydroxy acid from rooibos (Aspalathus linearis) with hypoglycemic activity.
PubMed:
Cell-free supernatants obtained from fermentation of cheese whey hydrolyzates and phenylpyruvic acid by Lactobacillus plantarum as a source of antimicrobial compounds, bacteriocins, and natural aromas.
PubMed:
Obesity-related metabolomic analysis of human subjects in black soybean peptide intervention study by ultraperformance liquid chromatography and quadrupole-time-of-flight mass spectrometry.
PubMed:
Determination of α-keto acids in pork meat and Iberian ham via tandem mass spectrometry.
PubMed:
Characterisation of volatile and non-volatile metabolites in etiolated leaves of tea (Camellia sinensis) plants in the dark.
PubMed:
Variation in phenolic content and antioxidant activity of fermented rooibos herbal tea infusions: role of production season and quality grade.
PubMed:
Characterization of D-lactate dehydrogenase producing D-3-phenyllactic acid from Pediococcus pentosaceus.
PubMed:
Characterization of D-lactate dehydrogenase from Pediococcus acidilactici that converts phenylpyruvic acid into phenyllactic acid.
PubMed:
Kinetic optimisation of the reversed phase liquid chromatographic separation of rooibos tea (Aspalathus linearis) phenolics on conventional high performance liquid chromatographic instrumentation.
PubMed:
Strecker aldehydes and α-keto acids, produced by carbonyl-amine reactions, contribute to the formation of acrylamide.
PubMed:
Bioconversion of phenylpyruvate to phenyllactate: gene cloning, expression, and enzymatic characterization of D- and L1-lactate dehydrogenases from Lactobacillus plantarum SK002.
PubMed:
3-Phenyllactic acid production by substrate feeding and pH-control in fed-batch fermentation of Lactobacillus sp. SK007.
PubMed:
Model studies on the oxygen-induced formation of benzaldehyde from phenylacetaldehyde using pyrolysis GC-MS and FTIR.
PubMed:
Optimization of culture medium for the production of phenyllactic acid by Lactobacillus sp. SK007.
PubMed:
Purification and partial characterization of Lactobacillus species SK007 lactate dehydrogenase (LDH) catalyzing phenylpyruvic acid (PPA) conversion into phenyllactic acid (PLA).
PubMed:
Simultaneous determination of ketoacids and dicarbonyl compounds, key Maillard intermediates on the generation of aged wine aroma.
PubMed:
Biotransformation of phenylpyruvic acid to phenyllactic acid by growing and resting cells of a Lactobacillus sp.
PubMed:
Chemical conversion of alpha-amino acids into alpha-keto acids by 4,5-epoxy-2-decenal.
PubMed:
Inhibitory effects of green tea polyphenols on the production of a virulence factor of the periodontal-disease-causing anaerobic bacterium Porphyromonas gingivalis.
PubMed:
Involvement of manganese in conversion of phenylalanine to benzaldehyde by lactic acid bacteria.
PubMed:
Conversion of phenylalanine to benzaldehyde initiated by an aminotransferase in lactobacillus plantarum