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Merck
CN

148776

3-Hydroxyanthranilic acid

97%, for peptide synthesis

Synonym(s):

2-Amino-3-hydroxybenzoic acid

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About This Item

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

Key Documents

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Product Name

3-Hydroxyanthranilic acid, 97%

InChI key

WJXSWCUQABXPFS-UHFFFAOYSA-N

InChI

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

SMILES string

Nc1c(O)cccc1C(O)=O

assay

97%

form

solid

reaction suitability

reaction type: solution phase peptide synthesis

mp

240 °C (dec.) (lit.)

application(s)

peptide synthesis

Quality Level

200

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Related Categories

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>

General description

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

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

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

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000499763
0000499763
0000432669
0000432669
0000451042

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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
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