Thermorubin
Title: Thermorubin
CAS Registry Number: 11006-83-0
Literature References: Antibiotic substances isolated from Thermoactinomyces antibioticus: Craveri et al., Clin. Med. 71, 511 (1964); eidem, DE 1180891; eidem, US 3300379 (1964, 1967 both to Lepetit). Structure of thermorubin A, the major component: Moppett et al., J. Am. Chem. Soc. 94, 3269 (1972); revised structure: F. Johnson et al., ibid. 102, 5580 (1980). Inhibition of bacterial protein synthesis: G. Pirali et al., Biochim. Biophys. Acta 366, 310 (1974). Studies on mechanism of action: F. Lin, A. Wishnia, Biochemistry 21, 477, 484 (1982).
Properties: Orange-red rosettes and needles from chloroform, darkens 190°, chars 300° without melting. [a]D25 -14° (c = 0.4 in dioxane). Absorption max [dioxane-cyclohexane (1:1)]: 300, 328, 414, 430 nm (E1%1cm 1041, 1066, 313, 332). Sol in dioxane, pyridine, tetrahydrofuran, DMF, DMSO, concd alkalies, concd H2SO4, glacial acetic acid; slightly sol in methanol, ethanol, butanol, ethyl acetate, acetone, chloroform, benzene, cyclohexane. Practically insol in water, ether, petr ether, hexane. LD50 i.p. in mice: 300 mg/kg (Craveri, 1967).
Optical Rotation: [a]D25 -14° (c = 0.4 in dioxane)
Absorption maximum: Absorption max [dioxane-cyclohexane (1:1)]: 300, 328, 414, 430 nm (E1%1cm 1041, 1066, 313, 332)
Toxicity data: LD50 i.p. in mice: 300 mg/kg (Craveri, 1967)
 
Derivative Type: Diacetate
Properties: Crystals from ethyl acetate. Absorption max [0.1N HCl-dioxane (1:1)]: 337, 436, 462 nm (E1%1cm 1500, 113, 162).
Absorption maximum: Absorption max [0.1N HCl-dioxane (1:1)]: 337, 436, 462 nm (E1%1cm 1500, 113, 162)
 
Derivative Type: Thermorubin A
Molecular Formula: C32H24O12
Molecular Weight: 600.53
Percent Composition: C 64.00%, H 4.03%, O 31.97%
Properties: Dihydrate, orange-red rosettes from ethyl acetate. Absorption max (ethanol): 250, 300, 328, 435 nm (e 33700, 54640, 49980, 16300). pKa values: 4.7, 7.0, 9.0. Easily tautomerizes in soln. Thermally labile, decomposes rapidly in soln at temps >60°.
pKa: pKa values: 4.7, 7.0, 9.0
Absorption maximum: Absorption max (ethanol): 250, 300, 328, 435 nm (e 33700, 54640, 49980, 16300)

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