Title: Tectorigenin
CAS Registry Number: 548-77-6
CAS Name: 5,7-Dihydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-1-benzopyran-4-one
Additional Names: 4¢,5,7-trihydroxy-6-methoxyisoflavone
Molecular Formula: C16H12O6
Molecular Weight: 300.26
Percent Composition: C 64.00%, H 4.03%, O 31.97%
Literature References: Phytoalexin aglycon isolated from rhizomes of Iris tectorum Maxim., Iridaceae, the extract of which is used as a traditional Chinese medicine. Isoln of the glycoside and aglycon: S. Shibata, J. Pharm. Soc. Jpn. 37, 380 (1927), C.A. 21, 30508 (1927); from Iris germanica Linnaeus: A. Kawase et al., Agric. Biol. Chem. 37, 145 (1973). Structure: Asahina et al., J. Pharm. Soc. Jpn. 48, 1087 (1928), C.A. 23, 27181 (1929); Shriner et al., J. Am. Chem. Soc. 61, 2322 (1939). Synthesis: Farkas, Várady, Ber. 93, 1269 (1960); W. Baker et al., J. Chem. Soc. C 1970, 1219. Inhibition of cyclooxygenase-2 induction: K. Ohuchi et al., Recent Adv. Nat. Prod. Res., Proc. 3rd Int. Symp. 1999, 12-24. Antioxidant effects: K.-T. Lee et al., Arch. Pharmacal Res. 23, 461 (2000).
Properties: Pale yellow needles from ethanol, mp 225-226°. uv max (ethanol): 267-269, 338 nm (log e 4.41, 3.40).
Melting point: mp 225-226°
Absorption maximum: uv max (ethanol): 267-269, 338 nm (log e 4.41, 3.40)
Derivative Type: Tectoridin
CAS Registry Number: 611-40-5
Additional Names: Tectorigenin-7-glucoside; shekanin
Molecular Formula: C22H22O11
Molecular Weight: 462.40
Percent Composition: C 57.14%, H 4.80%, O 38.06%
Literature References: Identity with shekanin and structure: Mannich et al., Arch. Pharm. 275, 317 (1937). Synthesis: Várady, Acta Chim. Acad. Sci. Hung. 48, 181 (1966).
Properties: Colorless needles from ethanol, mp 256-258°. uv max (ethanol): 267-269, 336 nm (log e 4.62, 3.65). [a]D20 -29.4° (pyridine). Sol in pyridine, alcohol, water. Practically insol in organic solvents.
Melting point: mp 256-258°
Optical Rotation: [a]D20 -29.4° (pyridine)
Absorption maximum: uv max (ethanol): 267-269, 336 nm (log e 4.62, 3.65)
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