Homogentisic acid

Base Information

• Chemical Name: Homogentisic acid
• CAS No.: 451-13-8
• Molecular Formula: C8H8 O4
• Molecular Weight: 168.149
• Hs Code.: 29182900
• European Community (EC) Number: 207-192-7
• NSC Number: 88940
• UNII: NP8UE6VF08
• DSSTox Substance ID: DTXSID1060005
• Nikkaji Number: J5.750I
• Wikipedia: Homogentisic_acid
• Wikidata: Q416054
• Metabolomics Workbench ID: 37091
• Mol file: 451-13-8.mol

Synonyms:Acid, Homogentisic;Homogentisic Acid

Chemical Property of Homogentisic acid

Chemical Property:

• Appearance/Colour: off-white to tan crystals or crystalline powder
• Vapor Pressure: 1.71E-08mmHg at 25°C
• Melting Point: 150-152 °C(lit.)
• Refractive Index: 1.5090 (estimate)
• Boiling Point: 439.3°Cat760mmHg
• PKA: 4.4(at 25℃)
• Flash Point: 233.6°C
• PSA: 77.76000
• Density: 1.478g/cm³
• LogP: 0.72490
• Storage Temp.: 2-8°C
• Solubility.: Soluble in methanol.
• Water Solubility.: very faint turbidity
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 168.04225873
• Heavy Atom Count: 12
• Complexity: 168

Purity/Quality:

98% ^*data from raw suppliers

Homogentisic Acid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1=CC(=C(C=C1O)CC(=O)O)O
• Uses: An intermediate in the metabolism of tyrosine and phenylalanine. Occurs in plants and in the urine of alkaptonurics. 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).

Technology Process of Homogentisic acid

There total 39 articles about Homogentisic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

5-Hydroxy-2-coumaranone (2688-48-4) → homogentisic acid (451-13-8)

Guidance literature:

DOI:10.1055/s-1980-28931

Reference yield:

4-hydroxyphenylpiruvic acid (156-39-8) → 4-hydroxyphenylacetate (156-38-7) + (4-oxo-2,5-cyclohexadien-1-yl)acetic acid (55604-87-0) + homogentisic acid (451-13-8) + (S)-α,4-dihydroxy-benzeneacetic acid (13244-75-2)

Guidance literature:

With oxygen; iron(II) sulfate; In aq. phosphate buffer; at 25 ℃; pH=7; Enzymatic reaction;

DOI:10.1021/bi400534q

Reference yield:

4-hydroxyphenylpiruvic acid (156-39-8) → 4-hydroxyphenylacetate (156-38-7) + (4-oxo-2,5-cyclohexadien-1-yl)acetic acid (55604-87-0) + homogentisic acid (451-13-8)

Guidance literature:

With oxygen; iron(II) sulfate; In aq. phosphate buffer; at 25 ℃; pH=7; Reagent/catalyst; Kinetics; Enzymatic reaction;

DOI:10.1021/bi400534q

upstream raw materials:

5-Hydroxy-2-coumaranone

2-ethoxy-benzofuran-5-ol

(2,5-dihydroxy-phenyl)-glyoxylic acid

(2,5-dimethoxyphenyl)acetic acid

Downstream raw materials:

ethyl 2-(2,5-dihydroxyphenyl)acetate

5-Hydroxy-2-coumaranone

maleylacetoacetic acid

4,6-dioxo-oct-2t-enedioic acid

Refernces

• 1、 Crouch,Baldwin,Lee,MacKinnon,Zhang. "Initial studies on the substrate specificity of soluble recombinant 4- hydroxyphenylpyruvate dioxygenase from rat liver". . p. 1503 - 1506. Retrieved 1996.
• 2、 Sergeant, Martin J.,Harrison, Peter J.,Jenkins, Robert,Moran, Graham R.,Bugg, Timothy D. H.,Thompson, Andrew J.. "Phytotoxic effects of selected N-benzyl-benzoylhydroxamic acid metallo-oxygenase inhibitors: Investigation into mechanism of action". . p. 3461 - 3465. Retrieved 2013/11/06.