Rhodomycins
Title: Rhodomycins
Literature References: Antibiotic substance produced by Streptomyces purpurascens nov. sp.: Brockmann, Bauer, Naturwissenschaften 37, 492 (1950); Brockmann et al., Ber. 84, 700 (1951); GB 708749 (1954 to Bayer). Separation of rhodomycin A and rhodomycin B: Brockmann, Patt, Ber. 88, 1455 (1955). Isoln and structural elucidation of additional rhodomycins produced by Streptomyces stammes: Biedermann, Brauniger, Pharmazie 27, 782 (1972); Brockmann et al., Tetrahedron Lett. 1973, 3699. Total synthesis of racemic rhodomycinones (the aglycones of the rhodomycins): A. S. Kende, Y.-G. Tsay, Chem. Commun. 1977, 140.
 
Derivative Type: Rhodomycin A
CAS Registry Number: 23666-50-4
CAS Name: [7R-(7a,8b,10b)]-8-Ethyl-7,8,9,10-tetrahydro-1,6,8,11-tetrahydroxy-7,10-bis[[2,3,6-trideoxy-3-(dimethylamino)-a-L-lyxo-hexopyranosyl]oxy]-5,12-naphthacenedione
Additional Names: b-rhodomycin II
Molecular Formula: C36H48N2O12
Molecular Weight: 700.77
Percent Composition: C 61.70%, H 6.90%, N 4.00%, O 27.40%
Literature References: Dec on mild acidic hydrolysis into 1 mole b-rhodomycinone and 2 moles rhodosamine: Brockmann, Spohler, Naturwissenschaften 48, 716 (1961). Structure of b-rhodomycinone: Brockmann, Niemeyer, ibid. 570. Structure of rhodosamine: Brockmann, Spohler, ibid. 42, 154 (1955). Total structure: Brockmann et al., Tetrahedron Lett. 1969, 415.
 
Derivative Type: Dihydrochloride
Molecular Formula: C36H48N2O12.2HCl
Molecular Weight: 773.69
Percent Composition: C 55.89%, H 6.51%, N 3.62%, O 24.82%, Cl 9.16%
Properties: Red prisms from ethanol+ isopropanol, mp 205°. Freely sol in water, lower alcohols; sparingly sol in benzene, chloroform; practically insol in ether, petr ether.
Melting point: mp 205°
 
Derivative Type: Perchlorate
Molecular Formula: C36H48N2O12.2HClO4
Molecular Weight: 901.69
Percent Composition: C 47.95%, H 5.59%, N 3.11%, O 35.49%, Cl 7.86%
Properties: Minute red needles, mp 188°. Freely sol in methanol, acetone; sparingly sol in water, butanol.
Melting point: mp 188°
 
Derivative Type: Rhodomycin B
CAS Registry Number: 1404-52-0
CAS Name: [7R-(7a,8b,10b)]-8-Ethyl-7,8,9,10-tetrahydro-1,6,7,8,11-pentahydroxy-10-[[2,3,6-trideoxy-3-(dimethylamino)-a-L-lyxo-hexopyranosyl]oxy]-5,12-naphthacenedione
Molecular Formula: C28H31NO9
Molecular Weight: 525.55
Percent Composition: C 63.99%, H 5.95%, N 2.67%, O 27.40%
Literature References: Dec on mild acidic hydrolysis into 1 mole b-rhodomycinone and 1 mole rhodosamine: Brockmann, Spohler, ibid. 48, 716 (1961).
 
Derivative Type: Hydrochloride
Properties: Red prisms, mp 180°. Freely sol in lower alcohols; sparingly sol in water, acetone. Practically insol in chloroform, benzene.
Melting point: mp 180°

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