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Sigma-Aldrich

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
EC Number:
208-962-5
MDL number:
MFCD00007700
UNSPSC Code:
12352106
PubChem Substance ID:
24848918
NACRES:
NA.22

product name

3-Hydroxyanthranilic acid, 97%

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

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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)

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Metabolic engineering, 12(3), 223-232 (2009-11-28)
Phenolic esters like chlorogenic acid play an important role in therapeutic properties of many plant extracts. We aimed to produce phenolic esters in baker's yeast, by expressing tobacco 4CL and globe artichoke HCT. Indeed yeast produced phenolic esters. However, the
Raf Brouns et al.
Neurochemical research, 35(9), 1315-1322 (2010-05-22)
Post-stroke inflammation may induce upregulation of the kynurenine (KYN) pathway for tryptophan (TRP) oxidation, resulting in neuroprotective (kynurenic acid, KA) and neurotoxic metabolites (3-hydroxyanthranillic acid, 3-HAA). We investigated whether activity of the kynurenine pathway in acute ischemic stroke is related
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Cytokine induction of the enzyme indoleamine 2,3-dioxygenase (IDO) has been implicated in the development of major depressive disorder (MDD). IDO metabolizes tryptophan (TRP) into kynurenine (KYN), thereby decreasing TRP availability to the brain. KYN is further metabolized into several neurotoxins.
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