Basic information Description Referrence Safety Supplier Related
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4-Hydroxyphenylacetic acid

Basic information Description Referrence Safety Supplier Related

4-Hydroxyphenylacetic acid Basic information

Product Name:
4-Hydroxyphenylacetic acid
Synonyms:
  • (p-hydroxyphenyl)-aceticaci
  • 4-carboxymethylphenol
  • 4-Hydroxybenzeneacetic acid
  • 4-Hydroxyphenylacetic acid Vetec(TM) reagent grade, 98%
  • Arbidol Impurity F HCl
  • Levothyroxine Sodium Impurity d
  • NSC 27460
  • Acetic acid, (p-hydroxyphenyl)-
CAS:
156-38-7
MF:
C8H8O3
MW:
152.15
EINECS:
205-851-3
Product Categories:
  • C8Fluorescent Probes, Labels, Particles and Stains
  • Other Fluorescent Labels
  • Aromatic Phenylacetic Acids and Derivatives
  • Carbonyl Compounds
  • Carboxylic Acids
  • Fluorescent Labels
  • Aromatics
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • pharmaceutical
  • alcohol| carboxylic acid
  • 1
Mol File:
156-38-7.mol
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4-Hydroxyphenylacetic acid Chemical Properties

Melting point:
148-151 °C(lit.)
Boiling point:
234.6°C (rough estimate)
Density 
1.2143 (rough estimate)
refractive index 
1.4945 (estimate)
storage temp. 
Inert atmosphere,Room Temperature
solubility 
50g/l
pka
4.50±0.10(Predicted)
form 
Crystalline Powder
color 
White to cream or light tan
PH
2.0-2.4 (30g/l, H2O, 20℃)
Water Solubility 
Soluble in dimethyl sulfoxide and methanol. Slightly soluble in water.
BRN 
1448766
InChIKey
XQXPVVBIMDBYFF-UHFFFAOYSA-N
CAS DataBase Reference
156-38-7(CAS DataBase Reference)
NIST Chemistry Reference
Benzeneacetic acid, 4-hydroxy-(156-38-7)
EPA Substance Registry System
Benzeneacetic acid, 4-hydroxy- (156-38-7)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-24/25
WGK Germany 
3
RTECS 
AI2680000
Hazard Note 
Irritant
TSCA 
Yes
HS Code 
29182990

MSDS

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4-Hydroxyphenylacetic acid Usage And Synthesis

Description

4-Hydroxyphenylacetic acid is an acetate derivative used in the acylation of phenols and amines1. It is an active component of Chinese herb Aster tataricus which had been widely used in China for the treatment of pulmonary diseases, HBV, and carcinoma. It is an active metabolite of amino acid metabolism. Study has also shown that it can attenuate inflammation and edema through suppressing hypertonic and hypoxic induction of HIF-1α in seawater aspiration-induced lung injury in rats. In chemical industry, it is an intermediate used to synthesize atenolol and 3, 4-dihydroxyphenylacetic acid.

Referrence

  1. Liu, Zhongyang, et al. "4-Hydroxyphenylacetic Acid Attenuated Inflammation and Edema via Suppressing HIF-1α in Seawater Aspiration-Induced Lung Injury in Rats." International Journal of Molecular Sciences 15.7(2014):12861-84.
  2. Ng, T.B.; Liu, F.; Lu, Y.; Cheng, C.H.; Wang, Z. Antioxidant activity of compounds from the medicinal herb Aster tataricus. Comp. Biochem. Physiol. 2003, 136, 109–115. 
  3. Du, L.; Mei, H.F.; Yin, X.; Xing, Y.Q. Delayed growth of glioma by a polysaccharide from Aster tataricus involve upregulation of Bax/Bcl-2 ratio, activation of caspase-3/8/9, and downregulation of the Akt. Tumour Biol. 2014, 35, 1819–1825.

Chemical Properties

4-Hydroxyphenylacetic acid is a white to cream or light tan crystalline powder. sublimation. Insoluble in cold water, soluble in hot water, ether, ethanol, ethyl acetate. In the case of ferric chloride, it is a purple-green precipitate. It is used as a pharmaceutical raw material for the synthesis of cephalosporin antibiotics, antipyretic analgesics.

Uses

A compound present in olive oil. An important fine chemical intermediate with broad prospects for application development.

Uses

It is used as a reagent in the acylation of phenols and amines. It is also used for fluorometric determination of oxidative enzymes.

Preparation

4-Hydroxyphenylacetic acid is synthesized by diazotization and hydrolysis of 4-aminophenylacetic acid.
4-aminophenylacetic acid and alkali solution are prepared into sodium salt, and then sulfuric acid is added. Cool to 0°C, control the temperature at 0-5°C, and add sodium nitrate solution dropwise, and the reaction is completed for 0.5h. The obtained diazonium was added dropwise to dilute sulfuric acid at 90-95°C for about 1 hour, and the reaction was continued for 1 hour. The reaction solution was decolorized and filtered, cooled and extracted with ethyl acetate, and the extract was recovered with ethyl acetate to obtain 4-Hydroxyphenylacetic acid. The yield is about 85%.

Definition

ChEBI: 4-hydroxyphenylacetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. It has a role as a plant metabolite, a fungal metabolite, a human metabolite and a mouse metabolite. It is a monocarboxylic acid and a member of phenols. It derives from an acetic acid. It is a conjugate acid of a 4-hydroxyphenylacetate.

Purification Methods

Crystallise the acid from water or Et2O/pet ether. The p-bromophenacyl ester has m 117o (from EtOH). [Beilstein 10 II 112, 10 III 430, 10 IV 543.]

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