From Wikipedia, the free encyclopedia
3-Hydroxyanthranilic acid
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Names
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Preferred IUPAC name
2-Amino-3-hydroxybenzoic acid
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Identifiers
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ChEBI
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ChEMBL
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ChemSpider
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DrugBank
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ECHA InfoCard
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100.008.148
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KEGG
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MeSH
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3-Hydroxyanthranilic+Acid
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UNII
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InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11) YKey: WJXSWCUQABXPFS-UHFFFAOYSA-N YInChI=1/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11) Key: WJXSWCUQABXPFS-UHFFFAOYAB
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C1=CC(=C(C(=C1)O)N)C(=O)O c1cc(c(c(c1)O)N)C(=O)O
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Properties
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C7H7NO3
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Molar mass
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153.137 g·mol−1
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Appearance
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powder
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Density
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≈ 1 g/cm3
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Melting point
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240–265 °C (464–509 °F; 513–538 K)
[3] decomposes 227 °C (441 °F; 500 K)
[2] from dilute
HCl, decomposes
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low
[1]
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Solubility
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soluble in ether,
CHCl3, alcohols
[1]
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Solubility in
hydrochloric acid
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1 N:
[1] 1 g/100 ml
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Acidity (pKa)
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at 20 °C:
[2] 1 = 2.7, 2 = 5.19, 3 = 10.12
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UV-vis (λmax)
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298 nm
[2]
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Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
3-Hydroxyanthranilic acid is an
intermediate in the
metabolism of tryptophan. It is new
antioxidant isolated from
methanol extract of
tempeh. It is effective in preventing
autoxidation of
soybean oil and powder, while antioxidant 6,7,4'-trihydroxyisoflavone is not.
[4]
References
- ^
a
b
c
"3-Hydroxyanthranilic acid". Santa Cruz Biotechnology, Inc. Retrieved 2015-09-24.
- ^
a
b
c Armarego, Wilfred L.F.; Chai, Christina L.L. (2009).
Purification of Laboratory Chemicals (6th ed.). Elsevier Inc. p. 297.
ISBN
978-1-85617-567-8.
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^ Moline, Sheldon W.; Walker, H.C.; Schweigert, B.S. (1958).
"3-Hydroxyanthranilic Acid Metabolism: VII. Mechanism of Formation of Quinolinic Acid". Journal of Biological Chemistry. 234 (4): 880–883.
doi:
10.1016/S0021-9258(18)70194-4.
PMID
13654282. Retrieved 2015-09-24.
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^ Esaki, Hideo; Onozaki, Hiromichi; Kawakishi, Shunro; Osawa, Toshihiko (1996). "New Antioxidant Isolated from Tempeh". Journal of Agricultural and Food Chemistry. 44 (3): 696.
doi:
10.1021/jf950454t.
External links
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HAA concentration graph in lyophilized tempeh powder extract (in Indonesian)