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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
Preferred IUPAC name 2-Amino-3-hydroxybenzoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.008.148 Edit this at Wikidata
KEGG
MeSH 3-Hydroxyanthranilic+Acid
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)Key: WJXSWCUQABXPFS-UHFFFAOYSA-N
  • 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
Chemical formula C7H7NO3
Molar mass 153.137 g·mol
Appearance powder
Density ≈ 1 g/cm
Melting point 240–265 °C (464–509 °F; 513–538 K)
decomposes
227 °C (441 °F; 500 K)
from dilute HCl, decomposes
Solubility in water 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-vismax) 298 nm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

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.

References

  1. ^ "3-Hydroxyanthranilic acid". Santa Cruz Biotechnology, Inc. 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. 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.
  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

  • HAA concentration graph in lyophilized tempeh powder extract (in Indonesian)
Amino acid metabolism metabolic intermediates
Kacetyl-CoA
lysine
leucine
tryptophanalanine
G
G→pyruvate
citrate
glycine
serine
G→glutamate
α-ketoglutarate
histidine
proline
arginine
other
G→propionyl-CoA
succinyl-CoA
valine
isoleucine
methionine
threonine
propionyl-CoA
G→fumarate
phenylalaninetyrosine
G→oxaloacetate
Other
Cysteine metabolism


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