451-13-8

Name	HOMOGENTISIC ACID
CAS	451-13-8
EINECS(EC#)	207-192-7
Molecular Formula	C8H8O4
MDL Number	MFCD00004324
Molecular Weight	168.15
MOL File	451-13-8.mol

Chemical Properties

Appearance	off-white to tan crystals or crystalline powder
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.
form	crystalline
pka	4.4(at 25℃)
color	off-white to tan
Water Solubility	very faint turbidity
Merck	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 Data

Hazard Codes	Xi
Risk Statements	R36/37/38:Irritating to eyes, respiratory system and skin . less more
Safety Statements	S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36:Wear suitable protective clothing . less more
WGK Germany	3
RTECS	AH0589000
TSCA	Yes
HS Code	29182900

Hazard Information

Chemical Properties

off-white to tan crystals or crystalline powder

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).

Uses

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

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.]

Spectrum Detail

Well-known Reagent Company Product Information

Supplier

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