CAS 306-23-0 (+-)-3-(4-Hydroxyphenyl)lactic acid (HCID 9378)

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Basic information

CAS: 306-23-0
Standard SMILES: O=C(O)C(O)Cc1ccc(O)cc1
InChIKey: JVGVDSSUAVXRDY-UHFFFAOYSA-N
Molecular formula: C9H10O4
Average molar mass: 182.17 g/mol
Monoisotopic mass: 182.0579088

Overview

3-(4-hydroxyphenyl)lactic acid is a 2-hydroxy carboxylic acid that is lactic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. It has a role as a bacterial metabolite and a human metabolite. It is a member of phenols and a 2-hydroxy carboxylic acid. It is functionally related to a rac-lactic acid. It is a conjugate acid of a 3-(4-hydroxyphenyl)lactate.

Names & identifiers

Preferred name: (+-)-3-(4-Hydroxyphenyl)lactic acid
IUPAC: 2-hydroxy-3-(4-hydroxyphenyl)propanoic acid
English name: 3-(4-Hydroxyphenyl)lactate
Molecular formula: C9H10O4
Molecular weight: 182.17

Names & synonyms

306-23-03-(4-Hydroxyphenyl)lactic acidHPLA4-Hydroxyphenyllactic acidLactic acid, (p-hydroxyphenyl)-2-Hydroxy-3-(p-hydroxyphenyl)propionic acidbeta-(p-Hydroxyphenyl)lactic acidbeta-(4-Hydroxyphenyl)lactic acidLactic acid, 3-(p-hydroxyphenyl)-alpha,4-Dihydroxybenzenepropanoic acidEP7PS9S776Benzenepropanoic acid, alpha,4-dihydroxy-

Show more names

Lactic acid impurity 1204-hydroxyphenyllacticacid3-(4-HYDROXYPHENYL)LACTATEPARA-HYDROXYPHENYLLACTICACID2-Hydroxy-3-(4-hydroxyphenyl)3-(4-hydroxyphenyl)lacticacid3-(p-hydroxyphenyl)-lacticaci

CHEBI:17385(+-)-3-(4-Hydroxyphenyl)lactic acidRefChem:390667para-hydroxyphenyllactic acid2-Hydroxy-3-(4-hydroxyphenyl)propanoic acidHydroxyphenyllactic aciddl-p-Hydroxyphenyllactic acidDL-4-Hydroxyphenyllactic Acid

Database identifiers

CAS

Properties

Computed structural properties

XLogP: 0.3
Topological polar surface area: 77.8 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 4
Rotatable bonds: 3
Heavy atoms: 13
Formal charge: 0
Complexity: 172

Experimental & physicochemical properties

Solubility12.9 mg/mL at 16 °C

Physical DescriptionSolid

Collision Cross Section · 3 items

144.2 Å² [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

139.4 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

144 Å² [M+Na]+

Physicochemical properties

Melting point: 140 °C · 140 °C(Solv: water (7732-18-5))
Boiling point: 275.56 °C · 275.56°C (rough estimate)
Density: 1.2481 · 1.2481 (rough estimate)
refractive index: 1.4345 · 1.4345 (estimate)
storage temp.: 4 °C, · 4°C, away from moisture and light
solubility: 25 mg/ml; · DMF: 25 mg/ml; DMSO: 25 mg/ml; Ethanol: 25 mg/ml
pka: 3.8 · 3.80±0.10(Predicted)

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 39 reports by companies from 2 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

wgk: 3
hs_code: 2918.29.7500
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319
Precautionary statements: P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Chemistry & industry

Pharmacology

Tissue LocationsEpidermis

Cellular LocationsMitochondria

Applications

UsesDL-p-Hydroxyphenyllactic Acid is used as a reagent in the synthesis of 2-O-(4-coumaroyl)-3-(4-hydroxyphenyl)lactic acid, an important intermediate of rosmarinic acid biosynthesis.

UsesDL-p-Hydroxyphenyllactic acid is a precursor in the synthesis of rosmarinic acid that can be used for pharmaceutical and nutraceutical applications. It also exhibits antifungal activity.