HOMOGENTISIC ACID Chemical Properties

Melting point:

150-152 °C (lit.)

Boiling point:

257.07°C (rough estimate)

Density 

1.3037 (rough estimate)

refractive index 

1.5090 (estimate)

storage temp. 

2-8°C

solubility 

Soluble in methanol.

pka

4.4(at 25℃)

form 

crystalline

color 

off-white to tan

Water Solubility 

very faint turbidity

Merck 

14,4737

BRN 

2692860

LogP

0.860

CAS DataBase Reference

451-13-8(CAS DataBase Reference)

EPA Substance Registry System

Benzeneacetic acid, 2,5-dihydroxy- (451-13-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

AH0589000

TSCA 

Yes

HS Code 

29182900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

HOMOGENTISIC ACID Usage And Synthesis

Chemical Properties

off-white to tan crystals or crystalline powder

Uses

An intermediate in the metabolism of tyrosine and phenylalanine. Occurs in plants and in the urine of alkaptonurics.

Uses

Homogentisic acid may be used as an analytical reference standard for the quantification of the analyte in the following:

• Urine matrices using reversed-phase liquid chromatography tandem mass spectrometry (LC-MS/MS).
• Strawberry tree honey samples using reversed phase-high performance liquid chromatography (RP-HPLC) and ion chromatography (IC).

It may also be used as an internal standard for the determination of ascorbic acid (AA) and uric acid (UA) in human plasma samples using high-pressure liquid chromatography–electrochemical detection (HPLC–ECD).

Definition

ChEBI: Homogentisic acid is a dihydroxyphenylacetic acid having the two hydroxy substituents at the 2- and 5-positions. It has a role as a human metabolite and a plant metabolite. It is a dihydroxyphenylacetic acid and a member of hydroquinones. It is functionally related to a phenylacetic acid. It is a conjugate acid of a homogentisate.

General Description

Homogentisic acid (HGA) is an intermediate formed during the catabolism of phenylalanine and tyrosine. Alkaptonuria, a metabolic disorder, is characterized by high levels of HGA in serum and urine due to the deficiency of the enzyme homogentisic acid oxidase, which is involved in the degradation of HGA.

Purification Methods

Crystallise homogentisic acid from EtOH/CHCl3 or H2O (solubility is 85% at 25o). [Beilstein 10 IV 1506.]

HOMOGENTISIC ACID(451-13-8)Related Product Information

• HOMOGENTISIC ACID
• 2,5-DIHYDROXY-1,4-BENZENEDIACETIC ACID
• (2,5-Dimethoxyphenyl)acetic acid
• 2-(METHOXY)-5-(TRIFLUOROMETHOXY)PHENYLACETIC ACID
• HOMOGENTISIC ACID LACTONE,HOMOGENTISIC ACID GAMMA-LACTONE
• Phenylacetic acid
• 2,5-DIBENZYLOXYPHENYLACETIC ACID
• HOMOGENTISIC ACID, [RING-3H]
• AMINO-(2,4,5-TRIMETHOXY-PHENYL)-ACETIC ACID
• HOMOGENTISIC ACID ETHYL ESTER
• GAMMA-METHYL-L-LEUCINE
• 2-AMINO-2-(2,4,5-TRIMETHOXYPHENYL)ACETIC ACID HYDROCHLORIDE
• RARECHEM AL BO 1491
• (R)-AMINO-(2,5-DIMETHOXY-PHENYL)-ACETIC ACID
• (R)-AMINO-(2,4,5-TRIMETHOXY-PHENYL)-ACETIC ACID
• AKOS BBS-00006098
• AURORA KA-4815
• RARECHEM AL BO 1475