Phenylpyruvic acid
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Basic information
- CAS
156-06-9- Standard SMILES
O=C(O)C(=O)Cc1ccccc1- InChIKey
BTNMPGBKDVTSJY-UHFFFAOYSA-N- Molecular formula
- C9H8O3
- Average molar mass
- 164.16 g/mol
- Monoisotopic mass
- 164.04734411
Overview
Keto-phenylpyruvic acid is a 2-oxo monocarboxylic acid that is 3-phenylpropanoic acid substituted by an oxo group at position 2. It is an intermediate metabolite in the phenylalanine pathway. It has a role as a chromogenic compound, a fundamental metabolite and an EC 6.4.1.1 (pyruvate carboxylase) inhibitor. It is functionally related to a pyruvic acid. It is a conjugate acid of a keto-phenylpyruvate. It is a tautomer of an enol-phenylpyruvic acid.
Names & identifiers
- Preferred name
- Phenylpyruvic acid
- IUPAC
- 2-oxo-3-phenylpropanoic acid
- English name
- 3-Phenylpyruvic acid
- Molecular formula
- C9H8O3
- Molecular weight
- 164.16
Names & synonyms
phenylpyruvic acid156-06-92-Oxo-3-phenylpropanoic acid3-Phenylpyruvic acidbeta-Phenylpyruvic acid3-Phenyl-2-oxopropanoic acidketo-phenylpyruvic acid2-OXO-3-PHENYLPROPIONIC ACIDalpha-ketohydrocinnamic acidDTXSID1042281Benzenepropanoic acid, alpha-oxo-2-Oxo-3-phenylpropanic acid
Show more names
phenylpyruvicL-PHENYLPYRUVICACIDBENZYLGLYOXYLIC ACIDPhenylpyruvicAcid>Pyruvic acid, phenyl-
CHEBI:30851X7CO62M413alpha-oxo-benzenepropanoic acidDTXCID9022281RefChem:861822205-847-1phenylpyruvatePyruvic acid, phenyl-
Database identifiers
- CAS
156-06-9- PubChem CID
- 997
- DTXSID
DTXSID1042281- ChEMBL
CHEMBL1162488- ChEBI
CHEBI:30851
Properties
Computed structural propertiesFilling in
- XLogP
- 1.3
- Topological polar surface area
- 54.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 180
Experimental & physicochemical properties
Chemical ClassesOther Uses -> Food Additives
DrugsPharmaceuticals -> Listed in ZINC15
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
112 mg/mL
Soluble in water
Soluble (in ethanol)
Melting Point154 °C
Physical Description
Pale yellow or white crystalline powder; Hygroscopic; [Alfa Aesar MSDS]
Solid
White crystalline powder
Physicochemical properties
- Melting point
- 150 · 150-154 °C (lit.)
- Boiling point
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzenepropanoic acid, .alpha.-oxo-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Benzenepropanoic acid, .alpha.-oxo-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Hazards SummarySafe when used as a flavoring agent in food; [JECFA] May cause irritation; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- F
- 3-8-10-23
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29183000
- risk_code
- 36/37/38
- Signal word
- Danger
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Metabolite PathwaysPhenylalanine and Tyrosine Metabolism
Uses & manufacturing
UsesUsed as a flavoring agent; [FDA]
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationBenzenepropanoic acid, .alpha.-oxo-: INACTIVE
Applications
Usesα-Oxobenzenepropanoic Acid is a useful reagent for organic synthesis.
General DescriptionPhenylpyruvic acid reduces glucose-6-phosphate dehydrogenase activity without pre-incubation.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: A 2-oxo monocarboxylic acid that is 3-phenylpropanoic acid substituted by an oxo group at position 2. It is an intermediate metabolite in the phenylalanine pathway.
Related reactions
71 records
Compound notes
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