phenyl pyruvic acid
2-oxo-3-phenylpropionic acid
 
Notes:
Flavouring ingredient Phenylpyruvic_acid
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      Product(s):
      156-06-9 Phenylpyruvic Acid
       
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      Product(s):
      16-47500 3-PHENYLPYRUVIC ACID
       
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      Product(s):
      P0154 Phenylpyruvic Acid >93.0%(GC)(T)
       
Synonyms   Articles   Notes   Search
CAS Number: 156-06-9Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 205-847-1
FDA UNII: X7CO62M413
Nikkaji Web: J11.025F
Beilstein Number: 2207312
MDL: MFCD00002589
CoE Number: 8109
XlogP3-AA: 1.30 (est)
Molecular Weight: 164.16036000
Formula: C9 H8 O3
NMR Predictor: Predict (works with chrome or firefox)
Category: 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
JECFA Food Flavoring: 1478  2-oxo-3-phenylpropionic acid
DG SANTE Food Flavourings: 08.109  3-phenylpyruvic acid
FEMA Number: 3892 2-oxo-3-phenylpropionic acid
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF):156-06-9 ; 2-OXO-3-PHENYLPROPIONIC ACID
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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
 propylene glycol
 water, 6.522e+004 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor Type: honey
 
Odor Strength: medium ,
recommend smelling in a 10.00 % solution or less
 
Substantivity: 146 hour(s) at 1.00 % in propylene glycol
 
 sweet  acidic  honey  almond  weedy  phenolic  green  
Odor Description:
at 100.00 %. 
sweet acidic honey almond weedy phenolic green
Luebke, William tgsc, (2006)
 
 
Flavor Type: phenolic
 
 sweet  phenolic  grassy  honey  vegetable  
Taste Description:
at 80.00 ppm in water.  
sweet phenolic grassy honey vegetable
Luebke, William tgsc, (2006)
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Alfa Biotechnology
For experimental / research use only.
3-Phenylpyruvic acid 98%
BOC Sciences
For experimental / research use only.
Phenylpyruvic Acid
Parchem
phenyl pyruvic acid
Penta International
3-PHENYLPYRUVIC ACID
Sigma-Aldrich: Aldrich
For experimental / research use only.
Phenylpyruvic Acid 98%
TCI AMERICA
For experimental / research use only.
Phenylpyruvic Acid >93.0%(GC)(T)
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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
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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
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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
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References:
 2-oxo-3-phenylpropanoic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 997
Pubchem (sid): 134974264
Pherobase: View
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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
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Potential Blenders and core components note
 
For Odor
acidic
 cyclohexyl acetic acidFL/FR
aldehydic
 citronellyl oxyacetaldehydeFL/FR
animal
para-cresyl phenyl acetateFL/FR
1,2,3,4-tetrahydroquinolineFR
anisic
para-anisyl phenyl acetateFL/FR
balsamic
 guaiacyl phenyl acetateFL/FR
2-phenyl propyl alcoholFL/FR
caramellic
 immortelle absoluteFL/FR
cereal
 bran absoluteFR
chocolate
isoamyl phenyl acetateFL/FR
 cocoa pentenalFL/FR
dairy
 methyl butyl phenyl acetateFL/FR
fatty
 methyl (E)-2-hexenoateFL/FR
 cardamom absoluteFL/FR
 citronellyl isovalerateFL/FR
 citronellyl phenyl acetateFL/FR
 citronellyl valerateFL/FR
 decyl formateFR
 ethyl hydrocinnamateFL/FR
 ethyl phenyl acetateFL/FR
 genet concreteFR
 geranyl anthranilateFR
 geranyl phenyl acetateFL/FR
 honeysuckle absoluteFR
 hyacinth acetalsFL/FR
 kewda absolute 
 kewda oilCS
 linalyl phenyl acetateFL/FR
 octyl isovalerateFL/FR
bitter orangeflower absolute moroccoFL/FR
 phenethyl acetateFL/FR
 phenethyl anthranilateFL/FR
 phenethyl benzoateFL/FR
 phenethyl hexanoateFL/FR
 phenethyl phenyl acetateFL/FR
 phenethyl propionateFL/FR
 phenyl glycol diacetateFR
3-phenyl propyl formateFL/FR
(E)-2-phenyl-1(2)-propene-1-yl acetateFR
isopropyl anthranilateFL/FR
isopropyl phenyl acetateFL/FR
 rhodinyl phenyl acetateFL/FR
 rose absolute (rosa centifolia) moroccoFL/FR
 rose carboxylateFR
 rose concrete (rosa centifolia)FR
 tuberose absolute (from concrete)FL/FR
 tuberose absolute (from pommade)FL/FR
 wallflower absoluteFR
fruity
 allyl phenoxyacetateFL/FR
(E)-beta-damasconeFL/FR
beta-damasconeFL/FR
(Z)-3-octen-1-yl propionateFL/FR
 osmanthus flower absoluteFL/FR
 strawberry glycidate 1 (aldehyde C-16 (so-called))FL/FR
 strawberry glycidate 2FL/FR
green
(E)-2-hexen-1-yl phenyl acetateFL/FR
4-methyl-4-phenyl pentanoneFR
(Z,Z)-3,6-nonadien-1-olFL/FR
 phenyl acetaldehydeFL/FR
hay
 beeswax absoluteFL/FR
herbal
 apium graveolens seed oilFL/FR
 apium graveolens seed oil indiaFL/FR
 artemisyl ketoneFL/FR
 celery seed oil replacerFR
 celery specialtyFR
american elder flower absoluteFR
 matricaria chamomilla flower oilFL/FR
honey
 allyl phenyl acetateFL/FR
 butyl phenyl acetateFL/FR
 methyl hydrocinnamateFL/FR
 methyl phenyl acetateFL/FR
 phenethyl furoateFL/FR
 phenyl acetic acidFL/FR
 propyl phenyl acetateFL/FR
melon
(Z)-6-nonen-1-olFL/FR
minty
 agathosma crenulata leaf oilFL/FR
musty
 cocoa butenalFL/FR
 tobacco specialtyFR
spicy
 carnation absoluteFR
isoeugenyl phenyl acetateFL/FR
 eugenyl phenyl acetateFL/FR
thujonic
 cistus cyclohexanoneFL/FR
waxy
 dihydrocitronellyl acetateFL/FR
1-dodecanolFL/FR
 waxy acetateFR
woody
 santalyl phenyl acetateFL/FR
 
For Flavor
 
No flavor group found for these
1-acetyl cyclohexyl acetateFL
 artemisyl ketoneFL/FR
 cistus cyclohexanoneFL/FR
 citronellyl isovalerateFL/FR
 citronellyl valerateFL/FR
 dihydrocitronellyl acetateFL/FR
 ethyl hydrocinnamateFL/FR
 eugenyl phenyl acetateFL/FR
 fig leaf absoluteFL
(E)-2-hexen-1-yl phenyl acetateFL/FR
 kewda absolute 
 linalyl phenyl acetateFL/FR
 methyl (E)-2-hexenoateFL/FR
3-methyl crotonic acidFL
 methyl hydrocinnamateFL/FR
 octyl isovalerateFL/FR
 phenethyl furoateFL/FR
3-phenyl propyl formateFL/FR
isopropyl anthranilateFL/FR
 santalyl phenyl acetateFL/FR
beta-damasconeFL/FR
anisic
para-anisyl phenyl acetateFL/FR
aromatic
 hyacinth acetalsFL/FR
brown
 beeswax absoluteFL/FR
citrus
 citronellyl oxyacetaldehydeFL/FR
dairy
 methyl butyl phenyl acetateFL/FR
floral
isoamyl phenyl acetateFL/FR
 cardamom absoluteFL/FR
 citronellyl phenyl acetateFL/FR
 cocoa pentenalFL/FR
 geranyl phenyl acetateFL/FR
 methyl phenyl acetateFL/FR
bitter orangeflower absolute moroccoFL/FR
 phenethyl anthranilateFL/FR
 phenethyl benzoateFL/FR
 phenethyl propionateFL/FR
 phenyl acetic acidFL/FR
 rose absolute (rosa centifolia) moroccoFL/FR
 tuberose absolute (from concrete)FL/FR
 tuberose absolute (from pommade)FL/FR
fruity
 allyl phenoxyacetateFL/FR
(E)-beta-damasconeFL/FR
(Z)-3-octen-1-yl propionateFL/FR
 osmanthus flower absoluteFL/FR
 strawberry glycidate 1 (aldehyde C-16 (so-called))FL/FR
 strawberry glycidate 2FL/FR
green
 cocoa butenalFL/FR
(E)-3-hexenoic acidFL
 immortelle absoluteFL/FR
2-phenyl propyl alcoholFL/FR
herbal
 apium graveolens seed oilFL/FR
 apium graveolens seed oil indiaFL/FR
 celery oleoresinFL
 matricaria chamomilla flower oilFL/FR
honey
 allyl phenyl acetateFL/FR
 butyl phenyl acetateFL/FR
 ethyl phenyl acetateFL/FR
 phenethyl acetateFL/FR
 phenethyl phenyl acetateFL/FR
 phenyl acetaldehydeFL/FR
isopropyl phenyl acetateFL/FR
 propyl phenyl acetateFL/FR
minty
 agathosma crenulata leaf oilFL/FR
phenolic
para-cresyl phenyl acetateFL/FR
 guaiacyl phenyl acetateFL/FR
soapy
1-dodecanolFL/FR
sour
2,4-dimethyl-2-pentenoic acidFL
spicy
isoeugenyl phenyl acetateFL/FR
sweet
 cyclohexyl acetic acidFL/FR
waxy
(Z,Z)-3,6-nonadien-1-olFL/FR
(Z)-6-nonen-1-olFL/FR
 phenethyl hexanoateFL/FR
 rhodinyl phenyl acetateFL/FR
 
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Potential Uses:
 floralFR
 flower shopFR
 grass 
 honeyFR
 tobaccoFR
 vegetableFL
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Occurrence (nature, food, other): note
 found in nature
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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
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Articles:
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
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