4-Hydroxyphenylacetic acid

Names

[ CAS No. ]:
156-38-7

[ Name ]:
4-Hydroxyphenylacetic acid

[Synonym ]:
4-Hydroxyphenyl acetic acid
2-(4-Hydroxyphenyl)acetic acid
4-hydroxyphenylacetic acid
(p-hydroxyphenyl)-Acetic acid
(4-Hydroxy-phenyl)-acetic acid
4-Hydroxy-Benzeneacetic acid
(4-Hydroxyphenyl)acetic acid
MFCD00004347
Benzeneacetic acid, 4-hydroxy-
EINECS 205-851-3
PHPA

Biological Activity

[Description]:

4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1].

[Related Catalog]:

Signaling Pathways >> NF-κB >> Keap1-Nrf2

Natural Products >> Phenols

Research Areas >> Metabolic Disease

[Target]

Nrf2[1]

[In Vivo]

4-Hydroxyphenylacetic acid (6, 12, or 25 mg/kg) increases Nrf2 translocation to the nucleus and enhances the activity of phase II and antioxidant enzymes. The protein levels of nuclear Nrf2 are increased by 170% and 230% in pre-treated 12 and 25 mg/kg 4-Hydroxyphenylacetic acid groups, respectively, compared with the control group.The 4-Hydroxyphenylacetic acid pretreatment at a final dose of 25 mg/kg markedly and selectively up-regulated the target genes of phase II enzymes and resulted in higher up-regulation than that of the control group by 270%, 400%, and 500% or UGT1A1, UGT1A9, and SULT2A1, respectively. 4-Hydroxyphenylacetic acid also suppresses the expression of CYP2E1[1].

[References]

[1]. Zhao H, et al. 4-Hydroxyphenylacetic Acid Prevents Acute APAP-Induced Liver Injury by Increasing Phase IIand Antioxidant Enzymes in Mice. Front Pharmacol. 2018 Jun 19;9:653.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
346.6±17.0 °C at 760 mmHg

[ Melting Point ]:
148-151 °C(lit.)

[ Molecular Formula ]:
C₈H₈O₃

[ Molecular Weight ]:
152.147

[ Flash Point ]:
177.6±17.4 °C

[ Exact Mass ]:
152.047348

[ PSA ]:
57.53000

[ LogP ]:
0.77

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.596

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AI2680000

CHEMICAL NAME :: Acetic acid, (p-hydroxyphenyl)-

CAS REGISTRY NUMBER :: 156-38-7

BEILSTEIN REFERENCE NO. :: 1448766

LAST UPDATED :: 199803

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C8-H8-O3

MOLECULAR WEIGHT :: 152.16

WISWESSER LINE NOTATION :: QV1R DQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FRPSAX Farmaco, Edizione Scientifica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 13,286,1958

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
AI2680000

[ HS Code ]:
2918290000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918290000

[ Summary ]:
HS: 2918290000 other carboxylic acids with phenol function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) VAT:17.0% MFN tariff:6.5% General tariff:30.0%

Articles

HMDB: a knowledgebase for the human metabolome.

Nucleic Acids Res. 37(Database issue) , D603-10, (2009)

The Human Metabolome Database (HMDB, http://www.hmdb.ca) is a richly annotated resource that is designed to address the broad needs of biochemists, clinical chemists, physicians, medical geneticists, ...

Age-related reference values for urinary organic acids in a healthy Turkish pediatric population.

Clin. Chem. 40(6) , 862-6, (1994)

Organic acid concentrations were quantified by gas chromatography and the individual acids identified by mass spectrometry in urine specimens from a healthy Turkish pediatric population of ages 2 days...

Prediction of skeletal muscle and fat mass in patients with advanced cancer using a metabolomic approach.

J. Nutr. 142(1) , 14-21, (2012)

Urine and plasma metabolites originate from endogenous metabolic pathways in different organs and exogenous sources (diet). Urine and plasma were obtained from advanced cancer patients and investigate...

Related Compounds

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