4-Hydroxyphenylpyruvic Acid (HCID 979)

Overview

4-hydroxyphenylpyruvic acid is a 2-oxo monocarboxylic acid that is pyruvic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. It has a role as a human metabolite. It is a member of phenols and a 2-oxo monocarboxylic acid. It is functionally related to a pyruvic acid. It is a conjugate acid of a 3-(4-hydroxyphenyl)pyruvate.

Names & identifiers

Preferred name: 4-Hydroxyphenylpyruvic Acid
IUPAC: 3-(4-hydroxyphenyl)-2-oxopropanoic acid
English name: 4-Hydroxyphenylpyruvic acid
Molecular formula: C9H8O4
Molecular weight: 180.16

Names & synonyms

4-Hydroxyphenylpyruvic acid156-39-83-(4-Hydroxyphenyl)-2-oxopropanoic acidp-Hydroxyphenylpyruvic acid(P-HYDROXYPHENYL)PYRUVIC ACID3-(p-Hydroxyphenyl)pyruvic acid(4-hydroxyphenyl)pyruvic acid3-(p-Hydroxyphenyl)-2-oxopropanoic acidBenzenepropanoic acid, 4-hydroxy-alpha-oxo-4-Hydroxy alpha-oxobenzenepropanoic acid0YP1694WNQCHEBI:15999

Show more names

Hydroxyphenylpyruvic acid3-(4-Hydroxyphenyl)pyruvateTyrosine metabolismTAUTOMERASE4-Hydrixyphenyruvic acidp-hydroxyphenyl-pyruvicaci

DTXSID80166017RefChem:99392para-hydroxyphenylpyruvic acidDTXCID9088508205-852-93-hydroxy-2-oxo-3-phenylpropanoic acidTestacid4-hydroxyphenylpyruvate

Database identifiers

CAS: 156-39-8
PubChem CID: 979
DTXSID: DTXSID80166017
ChEMBL: CHEMBL607712
ChEBI: CHEBI:15999
UNII: 0YP1694WNQ
EC Number: 205-852-9
Nikkaji: J101.877I

Properties

Computed structural properties

XLogP: 0.9
Topological polar surface area: 74.6 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 3
Heavy atoms: 13
Formal charge: 0
Complexity: 204

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

SpringerMaterials PropertiesAngular frequency

Melting Point219 - 220 °C

Physical DescriptionSolid

Collision Cross Section · 2 items

145.75 Å² [M-H]- [CCS Type: DT; Method: stepped-field]

147.1 Å² [M-H]-

Physicochemical properties

Melting point: 219 · 219-220 °C (dec.) (lit.)
Boiling point: 272.96 °C · 272.96°C (rough estimate)
Density: 1.2933 · 1.2933 (rough estimate)
refractive index: 1.45 · 1.4500 (estimate)
storage temp.: Inert atmosphere,Room Temperature
solubility: 50 mg/mL · ethanol: soluble50mg/mL
form: crystalline
pka: 2.5 · 2.50±0.54(Predicted)
color: off-white to tan
Water Solubility: slightly soluble
BRN: 2691632 · 2691632
Stability: Hygroscopic
InChI: 1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)
InChIKey: KKADPXVIOXHVKN-UHFFFAOYSA-N
SMILES: OC(=O)C(=O)Cc1ccc(O)cc1
CAS DataBase Reference: 156 · 156-39-8(CAS DataBase Reference)
FDA UNII: 0 YP1694WNQ · 0YP1694WNQ
NIST Chemistry Reference: 4 · Benzenepropanoic acid, 4-hydroxy-«alpha»-oxo-(156-39-8)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319
Precautionary statements: 264 · P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-37/39
WGK Germany: 3 · 3
RTECS: 1000000 · UZ1000000
HS Code: 29189900 · 29189900
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2

Safety & regulation

GHS classification

GHS Classification · 4 items

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 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
rtecs: UZ1000000
hs_code: 29189900
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-37/39
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2
Precautionary statements: P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313

Chemistry & industry

Pharmacology

Tissue LocationsPlacenta

Cellular LocationsCytoplasm

Metabolite PathwaysAlkaptonuria

Applications · 2 items

Uses4-Hydroxyphenylpyruvic Acid is general organic reagent used in the synthesis of latifolicinin A analogs as inhibitors of breast cancer. Also used in the preparation of amperometric biosensors for β-triketone herbicides based on hydroxyphenylpyruvate.

General Description4-hydroxyphenylpyruvic acid can be determined in pork meat and Iberian ham samples by a sensitive method of multiple reaction monitoring (MRM) by mass spectrometry.