| Identification | More | [Name]
HOMOGENTISIC ACID | [CAS]
451-13-8 | [Synonyms]
1,4-HYDROQUINONEACETIC ACID
2,5-DIHYDROXYPHENYLACETIC ACID
HOMOGENTISIC ACID
(2,5-dihydroxyphenyl)-aceticaci
2,5-dihydroxy-benzeneaceticaci
2,5-dihydroxybenzeneaceticacid
alcapton
Homogentisic acid 2,5-Dihydroxyphenylacetic acid
homogentisic acid free acid
2-(2,5-dihydroxyphenyl)acetic acid
HOMOGENTISIC ACID(RG)
2,5-Dihydroxy-α-toluic acid
Homogentisinic acid | [EINECS(EC#)]
207-192-7 | [Molecular Formula]
C8H8O4 | [MDL Number]
MFCD00004324 | [Molecular Weight]
168.15 | [MOL File]
451-13-8.mol |
| Chemical Properties | Back Directory | [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 | [Major Application]
food and beverages | [InChI]
1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12) | [InChIKey]
IGMNYECMUMZDDF-UHFFFAOYSA-N | [SMILES]
OC(=O)Cc1cc(O)ccc1O | [LogP]
0.860 | [CAS DataBase Reference]
451-13-8(CAS DataBase Reference) | [EPA Substance Registry System]
Benzeneacetic acid, 2,5-dihydroxy- (451-13-8) |
| Hazard Information | Back Directory | [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.] |
|
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Sigma-Aldrich
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