3-Hydroxyanthranilic acid

3-Hydroxyanthranilic acid is an intermediate in the metabolism of tryptophan. It is new antioxidant isolated from methanol extract of tempeh. It is effective in preventing autoxidation of soybean oil and powder, while antioxidant 6,7,4'-trihydroxyisoflavone is not.

3-Hydroxyanthranilic acid
Names
Preferred IUPAC name
2-Amino-3-hydroxybenzoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.008.148
KEGG
MeSH 3-Hydroxyanthranilic+Acid
PubChem CID
UNII
  • InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11) Y
    Key: WJXSWCUQABXPFS-UHFFFAOYSA-N Y
  • InChI=1/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)
    Key: WJXSWCUQABXPFS-UHFFFAOYAB
SMILES
  • C1=CC(=C(C(=C1)O)N)C(=O)O
  • c1cc(c(c(c1)O)N)C(=O)O
Properties
C7H7NO3
Molar mass 153.137 g·mol−1
Appearance powder
Density ≈ 1 g/cm3
Melting point 240–265 °C (464–509 °F; 513–538 K)
decomposes
227 °C (441 °F; 500 K)
from dilute HCl, decomposes
low
Solubility soluble in ether, CHCl3, alcohols
Solubility in hydrochloric acid 1 N:
1 g/100 ml
Acidity (pKa) at 20 °C:
1 = 2.7, 2 = 5.19, 3 = 10.12
UV-vis (λmax) 298 nm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references
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