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3-Hydroxyanthranilic acid

CAT: 0804-HY-W001171-01Size: 50 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-W001171-01Size:50 mg
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Description
3-Hydroxyanthranilic acid is a tryptophan metabolite in the kynurenine pathway.3-hydroxyanthranilic acid has anti-inflammatory, neuroprotective, and lipid-lowering effects. 3-hydroxyanthranilic acid can be used for researches of cardiovascular diseases, tumors, and metabolic diseases[1][2][3][4][5][6][7][8].
CAS Number
548-93-6
UNSPSC
12352005
Hazard Statement
H302+H312+H332, H315, H319, H335, H351
Target
Endogenous Metabolite
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease
Applications
Metabolism-sugar/lipid metabolism
Field of Research
Cancer; Endocrinology; Metabolic Disease; Inflammation/Immunology; Neurological Disease; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/3-Hydroxyanthranilic_acid.html
Purity
99.95
Solubility
DMSO : 50 mg/mL (ultrasonic)
Smiles
O=C(O)C1=CC=CC(O)=C1N
Molecular Formula
C7H7NO3
Molecular Weight
153.14
Precautions
H302+H312+H332, H315, H319, H335, H351
References & Citations
[1]Lee WS, et al. The tryptophan metabolite 3-hydroxyanthranilic acid suppresses T cell responses by inhibiting dendritic cell activation. Int Immunopharmacol. 2013 Nov;17 (3) :721-6.|[2]Lee SM, et al. Tryptophan metabolite 3-hydroxyanthranilic acid selectively induces activated T cell death via intracellular GSH depletion. Immunol Lett. 2010 Aug 16;132 (1-2) :53-60. |[3]Lee WS, et al. The tryptophan metabolite 3-hydroxyanthranilic acid suppresses T cell responses by inhibiting dendritic cell activation. Int Immunopharmacol. 2013 Nov;17 (3) :721-6. |[4]Krause D, et al. The tryptophan metabolite 3-hydroxyanthranilic acid plays anti-inflammatory and neuroprotective roles during inflammation: role of hemeoxygenase-1. Am J Pathol. 2011 Sep;179 (3) :1360-72. |[5]Zhang L, et al. The tryptophan metabolite 3-hydroxyanthranilic acid lowers plasma lipids and decreases atherosclerosis in hypercholesterolaemic mice. Eur Heart J. 2012 Aug;33 (16) :2025-34. |[6]Pae HO, et al. 3-Hydroxyanthranilic acid, one of L-tryptophan metabolites, inhibits monocyte chemoattractant protein-1 secretion and vascular cell adhesion molecule-1 expression via heme oxygenase-1 induction in human umbilical vein endothelial cells. Atherosclerosis. 2006 Aug;187 (2) :274-84. |[7]Wang Q, et al. Tryptophan-Derived 3-Hydroxyanthranilic Acid Contributes to Angiotensin II-Induced Abdominal Aortic Aneurysm Formation in Mice In Vivo. Circulation. 2017 Dec 5;136 (23) :2271-2283. |[8]Zhu F, et al. The combination of Butyricicoccus pullicaecorum and 3-hydroxyanthranilic acid prevents postmenopausal osteoporosis by modulating gut microbiota and Th17/Treg. Eur J Nutr. 2024 Aug;63 (5) :1945-1959.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
Human Endogenous Metabolite

Chemical Information

3-Hydroxyanthranilic Acid

3-hydroxyanthranilic acid is an aminobenzoic acid that is benzoic acid substituted at C-2 by an amine group and at C-3 by a hydroxy group. It is an intermediate in the metabolism of the amino acid tryptophan. It has a role as a mouse metabolite and a human metabolite. It is an aminobenzoic acid and a monohydroxybenzoic acid. It is functionally related to an anthranilic acid. It is a conjugate acid of a 3-hydroxyanthranilate. It is a tautomer of a 2,3-dihydro-3-oxoanthranilic acid.

CAS Number548-93-6
PubChem CID86
IUPAC Name2-amino-3-hydroxybenzoic acid
Molecular FormulaC7H7NO3
Molecular Weight153.14
XLogP0.9
Topological Polar Surface Area83.6
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count1
Heavy Atom Count11
Formal Charge0
Complexity160
SMILES
C1=CC(=C(C(=C1)O)N)C(=O)O
InChI
InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)
InChIKey
WJXSWCUQABXPFS-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of 3-Hydroxyanthranilic Acid
CAS: 548-93-6
CID: 86
Formula: C7H7NO3
MW: 153.14
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight153.14
XLogP30.9
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count1
Exact Mass153.042593085
Monoisotopic Mass153.042593085
Topological Polar Surface Area83.6 Ų
Heavy Atom Count11
Formal Charge0
Complexity160
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes