Oosporein
Title: Oosporein
CAS Registry Number: 475-54-7
CAS Name: 2,2¢,5,5¢-Tetrahydroxy-4,4¢-dimethyl[bi-1,4-cyclohexadien-1-yl]-3,3¢,6,6¢-tetrone
Additional Names: 3,3¢,6,6¢-tetrahydroxy-5,5¢-dimethyl-2,2¢-bi-p-benzoquinone; chaetomidin; iso-oosporein
Molecular Formula: C14H10O8
Molecular Weight: 306.22
Percent Composition: C 54.91%, H 3.29%, O 41.80%
Literature References: Fungal pigment isolated from Oospora colorans van Beyma.: Kögl, van Wessem, Rec. Trav. Chim. 63, 5 (1944); from Chaetonium aureum Chivers and identity with chaetomidin: Lloyd et al., J. Chem. Soc. 1955, 2163; from Acremonium spp: Divekar et al., Can. J. Chem. 37, 2097 (1959); from Beauveria bassiana (Bals.) Vuill.: Vining et al., Can. J. Microbiol. 8, 931 (1962). Identity with iso-oosporein: Smith, Thomson, Tetrahedron 10, 148 (1960). Synthesis: J. Kalamar et al., Helv. Chim. Acta 57, 2368 (1974). Biosynthesis: E. Steiner et al., ibid. 2377.
Properties: Bronze plates from aq methanol, mp 290-295°. uv max (ethanol): 216, 287 nm (log e 3.51, 4.67).
Melting point: mp 290-295°
Absorption maximum: uv max (ethanol): 216, 287 nm (log e 3.51, 4.67)
 
Derivative Type: Tetraacetate
Molecular Formula: C22H28O12
Molecular Weight: 484.45
Percent Composition: C 54.54%, H 5.83%, O 39.63%
Properties: Yellow needles from methanol, mp 190°. uv max (ethanol): 262 nm (log e 4.41).
Melting point: mp 190°
Absorption maximum: uv max (ethanol): 262 nm (log e 4.41)
 
Derivative Type: Tetramethyl ether
Molecular Formula: C18H18O8
Molecular Weight: 362.33
Percent Composition: C 59.67%, H 5.01%, O 35.33%
Properties: Orange needles from aq methanol, mp 123°. uv max (ethanol): 285.5, 394 nm (log e 4.40, 2.98).
Melting point: mp 123°
Absorption maximum: uv max (ethanol): 285.5, 394 nm (log e 4.40, 2.98)

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