3-Hydroxyanthranilic acid

3-Hydroxyanthranilic acid
Names
	Preferred IUPAC name 2-Amino-3-hydroxybenzoic acid
Identifiers
CAS Number	548-93-6 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:15793 ;
ChEMBL	ChEMBL445304 ;
ChemSpider	84 ;
DrugBank	DB03644 ;
ECHA InfoCard	100.008.148
KEGG	C00632 ;
MeSH	3-Hydroxyanthranilic+Acid
PubChem CID	86;
UNII	1UQB1BT4OT ;
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) 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−1
Appearance	powder
Density	≈ 1 g/cm3
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-vis (λmax)	298 nm
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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

^ ^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.

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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