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3-Hydroxyanthranilic acid (CAS 548-93-6)

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Alternate Names:
3-Hydroxyanthranilic acid is also known as 2-Amino-3-hydroxybenzoic acid.
Application:
3-Hydroxyanthranilic acid is a tryptophan metabolite along the kynurenine pathway, shown to induce apoptosis in T cells.
CAS Number:
548-93-6
Purity:
≥94%
Molecular Weight:
153.14
Molecular Formula:
C7H7NO3
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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3-Hydroxyanthranilic acid is a tryptophan metabolite along the kynurenine pathway. 3-Hydroxyanthranilic acid may act to induce apoptosis in T cells. In macrophages, 3-Hydroxyanthranilic acid may act to inhibit nitric oxide synthase and to stimulate TGF-β production.


3-Hydroxyanthranilic acid (CAS 548-93-6) References

  1. Effect of 3-hydroxyanthranilic acid in the immunosuppressive molecules indoleamine dioxygenase and HLA-G in macrophages.  |  López, AS., et al. 2008. Immunol Lett. 117: 91-5. PMID: 18289708
  2. NO scavenging by 3-hydroxyanthranilic acid and 3-hydroxykynurenine: N-nitrosation leads via oxadiazoles to o-quinone diazides.  |  Backhaus, C., et al. 2008. Nitric Oxide. 19: 237-44. PMID: 18675929
  3. The tryptophan metabolite 3-hydroxyanthranilic acid plays anti-inflammatory and neuroprotective roles during inflammation: role of hemeoxygenase-1.  |  Krause, D., et al. 2011. Am J Pathol. 179: 1360-72. PMID: 21855684
  4. On the Biological Importance of the 3-hydroxyanthranilic Acid: Anthranilic Acid Ratio.  |  Darlington, LG., et al. 2010. Int J Tryptophan Res. 3: 51-9. PMID: 22084587
  5. The tryptophan metabolite 3-hydroxyanthranilic acid lowers plasma lipids and decreases atherosclerosis in hypercholesterolaemic mice.  |  Zhang, L., et al. 2012. Eur Heart J. 33: 2025-34. PMID: 22711758
  6. The tryptophan metabolite 3-hydroxyanthranilic acid suppresses T cell responses by inhibiting dendritic cell activation.  |  Lee, WS., et al. 2013. Int Immunopharmacol. 17: 721-6. PMID: 24029595
  7. The urinary ratio of 3-hydroxykynurenine/3-hydroxyanthranilic acid is an index to predicting the adverse effects of D-tryptophan in rats.  |  Shibata, K., et al. 2014. J Nutr Sci Vitaminol (Tokyo). 60: 261-8. PMID: 25297615
  8. Iron chelation and redox chemistry of anthranilic acid and 3-hydroxyanthranilic acid: A comparison of two structurally related kynurenine pathway metabolites to obtain improved insights into their potential role in neurological disease development.  |  Chobot, V., et al. 2015. J Organomet Chem. 782: 103-110. PMID: 25892823
  9. 3-Hydroxykynurenine and 3-Hydroxyanthranilic Acid Enhance the Toxicity Induced by Copper in Rat Astrocyte Culture.  |  Ramírez-Ortega, D., et al. 2017. Oxid Med Cell Longev. 2017: 2371895. PMID: 28831293
  10. Tryptophan-Derived 3-Hydroxyanthranilic Acid Contributes to Angiotensin II-Induced Abdominal Aortic Aneurysm Formation in Mice In Vivo.  |  Wang, Q., et al. 2017. Circulation. 136: 2271-2283. PMID: 28978552
  11. Overexpression of kynurenic acid and 3-hydroxyanthranilic acid after rat traumatic brain injury.  |  Mangas, A., et al. 2018. Eur J Histochem. 62: PMID: 30426733
  12. Kinetic Evaluation of Dye Decolorization by Fenton Processes in the Presence of 3-Hydroxyanthranilic Acid.  |  Santana, CS., et al. 2019. Int J Environ Res Public Health. 16: PMID: 31067822
  13. Kynurenine derivative 3-HAA is an agonist ligand for transcription factor YY1.  |  Shi, Z., et al. 2021. J Hematol Oncol. 14: 153. PMID: 34563230

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

3-Hydroxyanthranilic acid, 250 mg

sc-216460
250 mg
$66.00

3-Hydroxyanthranilic acid, 1 g

sc-216460A
1 g
$143.00

3-Hydroxyanthranilic acid, 5 g

sc-216460B
5 g
$194.00

3-Hydroxyanthranilic acid, 10 g

sc-216460C
10 g
$344.00

3-Hydroxyanthranilic acid, 25 g

sc-216460D
25 g
$717.00

2 questions: 1. What is the appearance of your product (3-HAA)(color). 2. What is the solubility, what is the choice of solvents. Thank you

Asked by: dsagher
Thank you for your question. 3-Hydroxyanthranilic acid (CAS 548-93-6) has the appearance of a Light Pink to Light Brown Solid. Soluble in 1N HCl (10 mg/ml), water (partly), ether, chloroform, and alcohols.
Answered by: Technical Support
Date published: 2017-02-04
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Rated 5 out of 5 by from ReyesReyes-Ocampo J; et al. (PubMed ID: 26254737) determined that 3-Hydroxyanthranilic acid increased cytotoxicity in rat cultured cortical astrocytes and induced circling behavior and morphological changes of injected animals. -SCBT Publication Review
Date published: 2015-06-10
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3-Hydroxyanthranilic acid is rated 5.0 out of 5 by 1.
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