Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

148776

Sigma-Aldrich

3-Hydroxyanthranilic acid

97%, for peptide synthesis

Synonym(s):

2-Amino-3-hydroxybenzoic acid

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Linear Formula:
HOC6H3(NH2)CO2H
CAS Number:
548-93-6
Molecular Weight:
153.14
EC Number:
208-962-5
MDL number:
MFCD00007700
UNSPSC Code:
12352106
PubChem Substance ID:
24848918
NACRES:
NA.22

product name

3-Hydroxyanthranilic acid, 97%

Quality Level

200

Assay

97%

form

solid

reaction suitability

reaction type: solution phase peptide synthesis

mp

240 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

Nc1c(O)cccc1C(O)=O

InChI

1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)

InChI key

WJXSWCUQABXPFS-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

General description

3-Hydroxyanthranilic acid is an aminobenzoic acid commonly used as an intermediate in various chemical reactions.

Application

<ul>
<li><strong>Direct enzyme inhibition to mitigate quinolinic acid formation:</strong> Used to synthesize 2-amino-3-carboxymuconic semialdehyde (ACMS) during the kynurenine pathway of Tryptophan catabolism (Sanz et al., 2022).</li>
</ul>

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

NO scavenging by 3-hydroxyanthranilic acid and 3-hydroxykynurenine: N-nitrosation leads via oxadiazoles to o-quinone diazides
C Backhaus, et al.
Nitric Oxide, 19, 237-244 (2008)
Guifang Gan et al.
Cell death discovery, 7(1), 173-173 (2021-07-08)
Sorafenib is the FDA-approved first-line target drug for HCC patients. However, sorafenib only confers 3-5 months of survival benefit with <30% of HCC patients. Thus, it is necessary to develop a sensitizer for hepatocellular carcinoma (HCC) to sorafenib. Here, we
Lei Zhang et al.
European heart journal, 33(16), 2025-2034 (2012-06-20)
Cardiovascular disease is the most common cause of death in the world and atherosclerosis, an inflammatory process in the vessel wall, accounts for the majority of these deaths. The tryptophan metabolite 3-hydroxyanthranilic acid (3-HAA) has been shown to inhibit inflammation
E R Werner et al.
Biological chemistry Hoppe-Seyler, 366(1), 99-102 (1985-01-01)
3-Hydroxyanthranilic acid was identified in lymphocyte cultures during allogeneic stimulation. The metabolite and the synthetic product have identical HPLC retention times, fluorescence spectra, fluorescence intensities as a function of pH value and electrochemical behaviour.
F A Teulings et al.
Acta vitaminologica et enzymologica, 29(1-6), 108-112 (1975-01-01)
In comparison with healthy age- and sex-comparable subjects, a significantly higher concentration of unconjugated 3-hydroxyanthranilic acid was detected in the urine of untreated bladder and kidney carcinoma patients. Because of tryptophan metabolite 3-hydroxyanthranilic acid is suspected to be involved in
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service