3-Hydroxyanthranilic acid

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3-Hydroxyanthranilic acid
Skeletal formula of 3-hydroxyanthranilic acid
Ball-and-stick model of the 3-hydroxyanthranilic acid molecule as a zwitterion
IUPAC name
2-Amino-3-hydroxybenzoic acid
3D model (JSmol)
ECHA InfoCard 100.008.148
MeSH 3-Hydroxyanthranilic+Acid
Molar mass 153.137 g·mol−1
Appearance powder
Density ≈ 1 g/cm3
Melting point 240–265 °C (464–509 °F; 513–538 K)[3]
227 °C (441 °F; 500 K)[2]
from dilute HCl, decomposes
Solubility soluble in ether, CHCl3, alcohols[1]
Solubility in hydrochloric acid 1 N:[1]
1 g/100 ml
Acidity (pKa) at 20 °C:[2]
1 = 2.7, 2 = 5.19, 3 = 10.12
UV-vismax) 298 nm[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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]


  1. ^ a b c "3-Hydroxyanthranilic acid". Santa Cruz Biotechnology, Inc. Retrieved 2015-09-24.
  2. ^ a b c 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. ^ 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. PMID 13654282. 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.

External links[edit]

  • HAA concentration graph in lyophilized tempeh powder extract (in Indonesian)