Title: Neomethymycin

CAS Registry Number: 497-73-4

CAS Name: (12R)-10-Deoxy-12-hydroxymethymycin

Molecular Formula: C25H43NO7

Molecular Weight: 469.61

Percent Composition: C 63.94%, H 9.23%, N 2.98%, O 23.85%

Literature References: Macrolide antibiotic found in the mother liquors from methymycin, q.v. Differs from methymycin only in the location of one hydroxyl group, which results in marked changes in chemical behavior: Djerassi, Halpern, J. Am. Chem. Soc. 79, 2022, 3926 (1957); Tetrahedron 3, 255 (1958). Production from Streptomyces venezuelae cultures: Dutcher et al., US 2916486 (1959 to Olin Mathieson). Synthesis of the aglycone, neomethynolide: J. Inanago et al., Chem. Lett. 1981, 1415.

Properties: Crystals from ether + hexane, mp 156-158°. [a]D25 +93°. uv max (ethanol): 227.5 nm (log e 4.10). Solvates easily and when crystallized from dilute acetone yields 1 cm long crystals of the acetone solvate. Soluble in alcohol, acetone, chloroform, benzene, ethyl acetate, ether. Slightly sol in water, dibutyl ether. Practically insol in hexane, aliphatic hydrocarbons. Compare also Picromycin.

Melting point: mp 156-158°

Optical Rotation: [a]D25 +93°

Absorption maximum: uv max (ethanol): 227.5 nm (log e 4.10)