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.[4]

3-Hydroxyanthranilic acid
Skeletal formula of 3-hydroxyanthranilic acid
Ball-and-stick model of the 3-hydroxyanthranilic acid molecule as a zwitterion
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
UNII
  • InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11) checkY
    Key: WJXSWCUQABXPFS-UHFFFAOYSA-N checkY
  • 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
  • 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)[1]
decomposes
227 °C (441 °F; 500 K)[2]
from dilute HCl, decomposes
low[3]
Solubility soluble in ether, CHCl3, alcohols[3]
Solubility in hydrochloric acid 1 N:[3]
1 g/100 ml
Acidity (pKa) at 20 °C:[2]
1 = 2.7, 2 = 5.19, 3 = 10.12
UV-vis (λmax) 298 nm[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

References
  1. Moline, Sheldon W.; Walker, H.C.; Schweigert, B.S. (1958). "3-Hydroxyanthranilic Acid Metabolism: VII. Mechanism of Formation of Quinolinic Acid". Journal of Biological Chemistry. 234 (4): 880–883. doi:10.1016/S0021-9258(18)70194-4. PMID 13654282. Retrieved 2015-09-24.
  2. Armarego, Wilfred L.F.; Chai, Christina L.L. (2009). Purification of Laboratory Chemicals (6th ed.). Elsevier Inc. p. 297. ISBN 978-1-85617-567-8.
  3. "3-Hydroxyanthranilic acid". Santa Cruz Biotechnology, Inc. Retrieved 2015-09-24.
  4. Esaki, Hideo; Onozaki, Hiromichi; Kawakishi, Shunro; Osawa, Toshihiko (1996). "New Antioxidant Isolated from Tempeh". Journal of Agricultural and Food Chemistry. 44 (3): 696. doi:10.1021/jf950454t.
  • HAA concentration graph in lyophilized tempeh powder extract (in Indonesian)


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