6253. Monorden

Nomenclature

CAS number: 12772-57-5
8-Chloro-1a,14,15,15a-tetrahydro-9,11-dihydroxy-14-methyl-6H-oxireno[e][2]benzoxacyclotetradecin-6,12(7H)-dione; 5-chloro-6-(7,8-epoxy-10-hydroxy-2-oxo-3,5-undecadienyl)-β-resorcylic acid μ-lactone; radicicol.
C18H17ClO6; mol wt 364.78.
C 59.27%, H 4.70%, Cl 9.72%, O 26.32%.

Description and references

Antibiotic substance from Monosporium bonorden: Delmotte, Delmotte-Plaquée, Nature 171, 344 (1953). Identity with radicicol: Mirrington et al., Tetrahedron Lett. 1964, 365. Structure: McCapra, Scott, ibid. 1964, 869; Mirrington et al., Aust. J. Chem. 19, 1265 (1966). Isoln: NL 6506173 (1965 to Sandoz).

Chemical structure

Properties

Crystals from chloroform, alcohol or benzene, mp 193.5°. [α]D20 +203° (chloroform). uv max (ethanol): 264, 272 nm (ε 13200, 13100).

Derivative

Diacetate.
C22H21ClO8; mol wt 448.85.
C 58.87%, H 4.72%, Cl 7.90%, O 28.52%.

Properties

Crystals, mp 189°. uv max: 275 nm (ε 13000).