3-Hydroxyanthranilic acid

3-Hydroxyanthranilic acid
Names


Preferred IUPAC name 2-Amino-3-hydroxybenzoic acid
Identifiers
CAS Number	548-93-6^Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:15793^Y
ChEMBL	ChEMBL445304^Y
ChemSpider	84^Y
DrugBank	DB03644^Y
ECHA InfoCard	100.008.148
KEGG	C00632^Y
MeSH	3-Hydroxyanthranilic+Acid
PubChem CID	86
UNII	1UQB1BT4OT^Y
CompTox Dashboard (EPA)	DTXSID40203290
InChI 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
Chemical formula	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)^[3] decomposes 227 °C (441 °F; 500 K)^[2] from dilute HCl, decomposes
Solubility in water	low^[1]
Solubility	soluble in ether, CHCl₃, alcohols^[1]
Solubility in hydrochloric acid	1 N:^[1] 1 g/100 ml
Acidity (pK_a)	at 20 °C:^[2] 1 = 2.7, 2 = 5.19, 3 = 10.12
UV-vis (λ_max)	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 ^YN ?) 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.^[4]

References

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

lysine→	Saccharopine Allysine α-Aminoadipic acid 2-Oxoadipic acid Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA
leucine→	β-Hydroxy β-methylbutyric acid β-Hydroxy β-methylbutyryl-CoA Isovaleryl-CoA α-Ketoisocaproic acid β-Ketoisocaproic acid β-Ketoisocaproyl-CoA β-Leucine β-Methylcrotonyl-CoA β-Methylglutaconyl-CoA β-Hydroxy β-methylglutaryl-CoA
tryptophan→alanine→	N′-Formylkynurenine Kynurenine Anthranilic acid 3-Hydroxykynurenine 3-Hydroxyanthranilic acid 2-Amino-3-carboxymuconic semialdehyde 2-Aminomuconic semialdehyde 2-Aminomuconic acid Glutaryl-CoA

glycine→ serine→	3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde
proline→	1-Pyrroline-5-carboxylic acid
arginine→	Agmatine Ornithine Citrulline Cadaverine Putrescine
other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

valine→	α-Ketoisovaleric acid Isobutyryl-CoA Methacrylyl-CoA 3-Hydroxyisobutyryl-CoA 3-Hydroxyisobutyric acid 2-Methyl-3-oxopropanoic acid
isoleucine→	2,3-Dihydroxy-3-methylpentanoic acid 2-Methylbutyryl-CoA Tiglyl-CoA 2-Methylacetoacetyl-CoA
methionine→	generation of homocysteine: S-Adenosyl methionine S-Adenosyl-L-homocysteine Homocysteine conversion to cysteine: Cystathionine α-Ketobutyric acid + Cysteine
threonine→	α-Ketobutyric acid
propionyl-CoA→	Methylmalonyl-CoA