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phenyl pyruvic acid

Chemical Structure

General Material Information

Preferred name phenyl pyruvic acid
Trivial Name Phenylpyruvic acid
Short Description 2-oxo-3-phenylpropionic acid
Formula C9 H8 O3
CAS Number 156-06-9
FEMA Number 3892
Flavis Number 8.109
ECHA Number 205-847-1
FDA UNII X7CO62M413
Nikkaji Number J11.025F
Beilstein Number 2207312
MDL MFCD00002589
COE Number 8109
xLogP3-AA 1.30 (est)
NMR Predictor External link
JECFA Food Flavoring 1478 2-oxo-3-phenylpropionic acid
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 156-06-9 ; 2-OXO-3-PHENYLPROPIONIC ACID
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
  • 2-oxo-3-phenylpropanoic acid
  • Benzenepropanoic acid, α-oxo-
  • Pyruvic acid, phenyl-
  • α-Oxobenzenepropanoic acid
  • 3-Phenylpyruvic acid
  • β-Phenylpyruvic acid
  • 3-Phenyl-2-oxopropanoic acid
  • Phenylpyroracemic acid
  • 2-Oxo-3-phenylpropionic acid

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

2-oxo-3-phenylpropanoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):997
Pubchem (sid):134974264
Pherobase:View
Publications by PubMed
Modeling of the total antioxidant capacity of rooibos (Aspalathus linearis) tea infusions from chromatographic fingerprints and identification of potential antioxidant markers.
Production of natural antimicrobial compound D-phenyllactic acid using Leuconostoc mesenteroides ATCC 8293 whole cells involving highly active D-lactate dehydrogenase.
Screening of phenylpyruvic acid producers and optimization of culture conditions in bench scale bioreactors.
Enzymatic production of D-3-phenyllactic acid by Pediococcus pentosaceus D-lactate dehydrogenase with NADH regeneration by Ogataea parapolymorpha formate dehydrogenase.
Effects of fermented rooibos (Aspalathus linearis) on adipocyte differentiation.
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.
Z-2-(β-D-glucopyranosyloxy)-3-phenylpropenoic acid, an α-hydroxy acid from rooibos (Aspalathus linearis) with hypoglycemic activity.
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.
Obesity-related metabolomic analysis of human subjects in black soybean peptide intervention study by ultraperformance liquid chromatography and quadrupole-time-of-flight mass spectrometry.
Determination of α-keto acids in pork meat and Iberian ham via tandem mass spectrometry.
Characterisation of volatile and non-volatile metabolites in etiolated leaves of tea (Camellia sinensis) plants in the dark.
Variation in phenolic content and antioxidant activity of fermented rooibos herbal tea infusions: role of production season and quality grade.
Characterization of D-lactate dehydrogenase producing D-3-phenyllactic acid from Pediococcus pentosaceus.
Characterization of D-lactate dehydrogenase from Pediococcus acidilactici that converts phenylpyruvic acid into phenyllactic acid.
Kinetic optimisation of the reversed phase liquid chromatographic separation of rooibos tea (Aspalathus linearis) phenolics on conventional high performance liquid chromatographic instrumentation.
Strecker aldehydes and α-keto acids, produced by carbonyl-amine reactions, contribute to the formation of acrylamide.
Bioconversion of phenylpyruvate to phenyllactate: gene cloning, expression, and enzymatic characterization of D- and L1-lactate dehydrogenases from Lactobacillus plantarum SK002.
3-Phenyllactic acid production by substrate feeding and pH-control in fed-batch fermentation of Lactobacillus sp. SK007.
Model studies on the oxygen-induced formation of benzaldehyde from phenylacetaldehyde using pyrolysis GC-MS and FTIR.
Optimization of culture medium for the production of phenyllactic acid by Lactobacillus sp. SK007.
Purification and partial characterization of Lactobacillus species SK007 lactate dehydrogenase (LDH) catalyzing phenylpyruvic acid (PPA) conversion into phenyllactic acid (PLA).
Simultaneous determination of ketoacids and dicarbonyl compounds, key Maillard intermediates on the generation of aged wine aroma.
Biotransformation of phenylpyruvic acid to phenyllactic acid by growing and resting cells of a Lactobacillus sp.
Chemical conversion of alpha-amino acids into alpha-keto acids by 4,5-epoxy-2-decenal.
Inhibitory effects of green tea polyphenols on the production of a virulence factor of the periodontal-disease-causing anaerobic bacterium Porphyromonas gingivalis.
Involvement of manganese in conversion of phenylalanine to benzaldehyde by lactic acid bacteria.
Conversion of phenylalanine to benzaldehyde initiated by an aminotransferase in lactobacillus plantarum

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
KEGG (GenomeNet):C00166
HMDB (The Human Metabolome Database):HMDB00205
FooDB:FDB008272
YMDB (Yeast Metabolome Database):YMDB00786
Export Tariff Code:2918.30.3000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 164.16035461426
Boiling Point 299 to 300°C @ 760 mm Hg
Vapor Pressure 0.001 mmHg @ 25 °C
Flash Point TCC Value 100 °C TCC
logP (o/w) 0.142 est
Solubility
alcohol Yes
propylene glycol Yes
water, 6.522e+004 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Honey
sweet, acidic, honey, almond, weedy, phenolic, green
Odor strength medium , recommend smelling in a 10.00 % solution or less
Substantivity 146 hour(s) at 1.00 % in propylene glycol
Luebke, William tgsc, (2006) At 100.00 %. sweet acidic honey almond weedy phenolic green
Flavor Type: Phenolic
sweet, phenolic, grassy, honey, vegetable
Luebke, William tgsc, (2006) At 80.00 ppm in water. sweet phenolic grassy honey vegetable

Potential Uses

Applications
Odor purposes Floral, Flower shop, Honey, Tobacco
Flavoring purposes Vegetable
Other purposes Grass

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 22 - Do not breath dust.
S 24/25 - Avoid contact with skin and eyes.
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:
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
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)
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: 18
Click here to view publication 18
average usual ppmaverage maximum ppm
baked goods: --
beverages(nonalcoholic): 0.5000010.00000
beverages(alcoholic): --
breakfast cereal: 1.000005.00000
cheese: 0.500005.00000
chewing gum: 1.000005.00000
condiments / relishes: --
confectionery froastings: 1.000005.00000
egg products: --
fats / oils: --
fish products: --
frozen dairy: --
fruit ices: 0.500005.00000
gelatins / puddings: 0.500005.00000
granulated sugar: --
gravies: --
hard candy: 1.000005.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: 0.500005.00000
nut products: --
other grains: 1.000005.00000
poultry: --
processed fruits: 0.100001.00000
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: 50.00000100.00000
snack foods: --
soft candy: 1.000005.00000
soups: --
sugar substitutes: 0.500005.00000
sweet sauces: 1.000005.00000

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):

Flavouring Group Evaluation 55 (FGE.55): Consideration of phenyl-substituted aliphatic alcohols and related aldehydes and esters evaluated by JECFA (63rd meeting) structurally related to phenethyl alcohol, aldehyde, esters and related phenylacetic acid esters evaluated by EFSA in FGE.14 (2005) and aryl-substituted saturated and unsaturated primary alcohol/aldehyde/acid/ester derivatives evaluated by EFSA in FGE.15 (2005) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):156-06-9
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :997
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-oxo-3-phenylpropanoic acid
Chemidplus:0000156069