3-Hydroxyanthranilic acid

3-Hydroxyanthranilic acid
Names


IUPAC name 2-Amino-3-hydroxybenzoic acid
Identifiers
CAS Number	548-93-6^N
ChEBI	CHEBI:15793^Y
ChEMBL	ChEMBL445304^Y
ChemSpider	84^Y
DrugBank	DB03644^Y
Jmol interactive 3D	Image Image
KEGG	C00632^Y
MeSH	3-Hydroxyanthranilic+Acid
PubChem	86
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	153.14 g·mol⁻¹
Appearance	powder
Density	≈ 1 g/cm³
Melting point	240–265 °C (464–509 °F; 513–538 K)^[1] decomposes 227 °C (441 °F; 500 K)^[2] from dilute HCl, decomposes
Solubility in water	partially soluble^[3]
Solubility	soluble in ether, CHCl₃, alcohols^[3]
Solubility in hydrochloric acid	1 N:^[3] 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

3-Hydroxyanthranilic acid is an intermediate in the metabolism of tryptophan. It's new antioxidant isolated from methanol extract of tempeh. It's effective in preventing autoxidation of soybean oil and powder, while antioxidant 6,7,4‘-trihydroxyisoflavone isn't.^[4]

References

↑ 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.
1 2 3 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.
1 2 3 "3-Hydroxyanthranilic acid". http://www.scbt.com/. Santa Cruz Biotechnology, Inc. Retrieved 2015-09-24. External link in |website= (help)
↑ 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 (Indonesian)

Amino acid metabolism metabolic intermediates

K→acetyl-CoA

lysine→	Saccharopine Allysine α-Aminoadipic acid α-Ketoadipate Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA

leucine→	α-Ketoisocaproic acid Isovaleryl-CoA 3-Methylcrotonyl-CoA 3-Methylglutaconyl-CoA HMG-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

G→pyruvate→citrate

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

G→glutamate→
α-ketoglutarate

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde

proline→	1-Pyrroline-5-carboxylic acid

arginine→	Agmatine Ornithine Cadaverine Putrescine

other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA

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 alpha-Ketobutyric acid+Cysteine

threonine→	α-Ketobutyric acid

propionyl-CoA→	Methylmalonyl-CoA

G→fumarate

phenylalanine→tyrosine→	4-Hydroxyphenylpyruvic acid Homogentisic acid 4-Maleylacetoacetic acid

G→oxaloacetate

see urea cycle

Other

Cysteine metabolism	Cysteine sulfinic acid

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