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
Names
IUPAC name
2-Amino-3-hydroxybenzoic acid
Identifiers
548-93-6 N
ChEBI CHEBI:15793 YesY
ChEMBL ChEMBL445304 YesY
ChemSpider 84 YesY
DrugBank DB03644 YesY
Jmol 3D model Interactive image
Interactive image
KEGG C00632 YesY
MeSH 3-Hydroxyanthranilic+Acid
PubChem 86
Properties
C7H7NO3
Molar mass 153.14 g·mol−1
Appearance powder
Density ≈ 1 g/cm3
Melting point 240–265 °C (464–509 °F; 513–538 K)[3]
decomposes
227 °C (441 °F; 500 K)[2]
from dilute HCl, decomposes
partially soluble[1]
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).
N verify (what is YesYN ?)
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]

References[edit]

  1. ^ a b c "3-Hydroxyanthranilic acid". http://www.scbt.com/. Santa Cruz Biotechnology, Inc. Retrieved 2015-09-24.  External link in |website= (help)
  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 (Indonesian)