Celesticetin

Title: Celesticetin
CAS Registry Number: 2520-21-0
CAS Name: 2-[(2-Hydroxybenzoyl)oxy]ethyl 6,8-dideoxy-7-O-methyl-6-[[[(2S)-1-methyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-D-erythro-a-D-galacto-octopyranoside
Additional Names: a-2-hydroxyethyl 6,8-dideoxy-7-O-methyl-6-(1-methyl-L-2-pyrrolidinecarboxamido)-1-thio-D-erythro-D-galacto-octopyranoside monosalicylate; S-demethyl-3¢-depropyl-S-[2-[(2-hydroxybenzoyl)oxy]ethyl]-7-O-methyllincomycin
Molecular Formula: C24H36N2O9S
Molecular Weight: 528.62
Percent Composition: C 54.53%, H 6.86%, N 5.30%, O 27.24%, S 6.07%
Literature References: Antibiotic substance produced by Streptomyces caelestis from a soil obtained from Emigration Canyon near Salt Lake City: DeBoer et al., Antibiot. Annu. 1954-1955, 831; Hoeksema et al., ibid. 837. Structure: Hoeksema, J. Am. Chem. Soc. 86, 4224 (1964); 90, 755 (1968).
Properties: Amphoteric, amorphous base. [a]D24 +126.6° (c = 0.5 in chloroform). uv max (0.01N alcoholic H2SO4): 240, 310 nm (E1%1cm 183.7, 80.6). Soluble in acidic or strongly basic aq solns, practically insol in the pH range of 7 to 10. Soluble in the more polar organic solvents, but not in ether or light hydrocarbons. Active against gram-positive organisms and plant pathogens such as B. stewartii, P. fascians, X. pruni at 0.5 g/ml. The antibacterial activity is rapidly destroyed in aq solns above pH 9 at 24°, but remains at pH 5 to 7 for at least 60 days. Celesticetin is more stable in acid than in basic solns, but is destroyed rapidly in 1N HCl at 100°. Cross resistance with erythromycin.
Optical Rotation: [a]D24 +126.6° (c = 0.5 in chloroform)
Absorption maximum: uv max (0.01N alcoholic H2SO4): 240, 310 nm (E1%1cm 183.7, 80.6)
Derivative Type: Salicylate
Properties: Monoclinic tablets, mp 139°. [a]D24 +90.2° (c = 0.5 in H2O). Sol in water.
Melting point: mp 139°
Optical Rotation: [a]D24 +90.2° (c = 0.5 in H2O)
Derivative Type: Oxalate
Properties: Crystals, mp 149-154°. [a]D24 +106.6° (c = 0.5 in H2O). Sol in water.
Melting point: mp 149-154°
Optical Rotation: [a]D24 +106.6° (c = 0.5 in H2O)
Celestin Blue Cellobiose Cellocidin Cellophane Celluloid