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3-hydroxy Anthranilic Acid (Synonyms: 3-HAA,NSC 522891)

カタログ番号GC13377

3-ヒドロキシ アントラニル酸は、キヌレニン経路のトリプトファン代謝産物です。

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3-hydroxy Anthranilic Acid 化学構造

Cas No.: 548-93-6

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Sample solution is provided at 25 µL, 10mM.

Description of 3-hydroxy Anthranilic Acid

3-Hydroxyanthranilic acid (3-HAA) is an intermediate in the metabolism of the amino acid tryptophan. 3-HAA is an aminobenzoic acid generated by substitution of benzoic acid at C-2 with an amine group and at C-3 by a hydroxy group. 3-Hydroxyanthranilic acid is a new antioxidant isolated from methanol extract of tempeh [1].

Tryptophan metabolism by the kynurenine pathway (KP) plays an important role in the pathogenesis of inflammatory, infectious, and degenerative diseases [2]. 3-HAA effectively suppressed glial cytokine and chemokine expression and reduced cytokine-induced neuronal death [2]. In astrocytes, 3-HAA induced the expression of hemeoxygenase-1 (HO-1), an antioxidant enzyme with anti-inflammatory and cytoprotective properties. In cultured adult human astrocytes, 3-HAA induced HO-1 expression, which has also been observed after injection to mouse brains [2]. 3-HAA acted as a co-antioxidant for α-tocopherol, inhibiting human low density lipoprotein and plasma lipid peroxidation [3]. 3-HAA inhibited nitric oxide (NO) synthase in macrophages and stimulated TGF-β production, suppressing pro-inflammatory activity of Th1 cells [1].

References:
[1] Stone T W, Stoy N, Darlington L G.  An expanding range of targets for kynurenine metabolites of tryptophan[J]. Trends in pharmacological sciences, 2013, 34(2): 136-143.
[2] Krause D, Suh H S, Tarassishin L, et al.  The tryptophan metabolite 3-hydroxyanthranilic acid plays anti-inflammatory and neuroprotective roles during inflammation: role of hemeoxygenase-1[J]. The American journal of pathology, 2011, 179(3): 1360-1372.
[3] Thomas, S. R.,Wittig, P.K. and Stocker, R. 3-Hydroxyanthranilic acid is an efficient, cell-derived co-antioxidant for α-tocopherol, inhibiting human low density lipoprotein and plasma lipid peroxidation. The Journal of Biological Chemisty 271, 2714-32721 (1996).

Chemical Properties of 3-hydroxy Anthranilic Acid

Cas No. 548-93-6 SDF
同義語 3-HAA,NSC 522891
Chemical Name 2-amino-3-hydroxy-benzoic acid
Canonical SMILES OC(C1=C(N)C(O)=CC=C1)=O
Formula C7H7NO3 M.Wt 153.1
溶解度 ≤30mg/ml in ethanol;30mg/ml in DMSO;30mg/ml in dimethyl formamide Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of 3-hydroxy Anthranilic Acid

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1 mg 5 mg 10 mg
1 mM 6.5317 mL 32.6584 mL 65.3168 mL
5 mM 1.3063 mL 6.5317 mL 13.0634 mL
10 mM 0.6532 mL 3.2658 mL 6.5317 mL
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