Aristolochic Acid

Title: Aristolochic Acid
CAS Registry Number: 313-67-7
CAS Name: 8-Methoxy-6-nitrophenanthro[3,4-d]-1,3-dioxole-5-carboxylic acid
Additional Names: 3,4-methylenedioxy-8-methoxy-10-nitro-1-phenanthrenecarboxylic acid; aristolochic acid-I; aristolochine
Molecular Formula: C17H11NO7
Molecular Weight: 341.27
Percent Composition: C 59.83%, H 3.25%, N 4.10%, O 32.82%
Literature References: One of a group of fourteen known, substituted 1-phenanthrenecarboxylic acids, aristolochic acids, that occur in Aristolochiaceae and in butterflies feeding on these plants. They are often accompanied by aristololactams, twelve of which have been characterized. Isoln: Gänshirt, Pharmazie 8, 584 (1953); Pailer et al., Monatsh. Chem. 86, 676 (1955); Coutts et al., J. Pharm. Pharmacol. 11, 607 (1959); Kupchan, Doskotch, J. Med. Pharm. Chem. 5, 657 (1962). Structure: Pailer et al., Monatsh. Chem. 87, 249 (1956). Synthesis: Kupchan, Wormser, J. Org. Chem. 30, 3792 (1965). Biosynthesis: Spenser, Tiwari, Chem. Commun. 1966, 55. Acute toxicity: U. Mengs, Arch. Toxicol. 59, 328 (1987). Review: D. B. Mix et al., J. Nat. Prod. 45, 657-666 (1982).
Properties: Shiny brown leaflets from DMF + hot water, dec 281-286°. uv max (ethanol): 390, 318, 250 nm (e 6500; 12000; 27000). Slightly sol in water; sol in alcohol, chloroform, ether, acetone, acetic acid, aniline, alkalies. Practically insol in benzene, carbon disulfide. LD50 in male, female mice, male, female rats (mg/kg): 38.4, 70.1, 82.5, 74.0 i.v.; 55.9, 106.1, 203.4, 183.9 orally (Mengs).
Absorption maximum: uv max (ethanol): 390, 318, 250 nm (e 6500; 12000; 27000)
Toxicity data: LD50 in male, female mice, male, female rats (mg/kg): 38.4, 70.1, 82.5, 74.0 i.v.; 55.9, 106.1, 203.4, 183.9 orally (Mengs)
Derivative Type: Methyl ester
Molecular Formula: C18H13NO7
Molecular Weight: 355.30
Percent Composition: C 60.85%, H 3.69%, N 3.94%, O 31.52%
Properties: Orange-yellow rods from hot methanol, mp 285-286°.
Melting point: mp 285-286°
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