Tetronasin
Title: Tetronasin
CAS Registry Number: 75139-06-9
CAS Name: 4-Hydroxy-3-[(2S)-2-[(1S,2S,6R)-2-[(1E)-3-hydroxy-2-[(2R,3R,6S)-tetrahydro-3-methyl-6-[(1E,3S)-3-[(2R,3S,5R)-tetrahydro-5-[(1S)-1-methoxyethyl]-3-methyl-2-furanyl]-1-butenyl]-2H-pyran-2-yl]-1-propenyl]-6-methylcyclohexyl]-1-oxopropyl]-2(5H)-furanone
Additional Names: antibiotic M139603
Manufacturers' Codes: ICI-139603; M-139603
Molecular Formula: C35H54O8
Molecular Weight: 602.80
Percent Composition: C 69.74%, H 9.03%, O 21.23%
Literature References: Polyether antibiotic produced by Streptomyces longisporoflavus NCIB 11426. Possesses a biosynthetically rare acid grouping in the form of an acyl tetronic acid moiety. Isoln and use in ruminants: D. H. Davies, G. L. F. Norris, GB 2027013; eidem, US 4279894 (1980, 1981 both to ICI). Physical data and crystal structure: D. H. Davies et al., Chem. Commun. 1981, 1073. Solution conformation and cation-binding properties: J. Grandjean, P. Laszlo, Tetrahedron Lett. 24, 3319 (1983). Synthetic studies: A. M. Doherty, S. V. Ley, ibid. 27, 105 (1986). Biosynthetic studies: J. M. Bulsing et al., Chem. Commun. 1984, 1301; D. M. Doddrell et al., ibid. 1302; A. K. Demetriadou et al., ibid. 1985, 408. Antimicrobial activity: C. J. Newbold et al., Appl. Environ. Microbiol. 54, 544 (1988). Effect on gain efficiency in cattle: S. J. Bartle et al., J. Anim. Sci. 66, 1502 (1988).
 
Derivative Type: Sodium salt
Molecular Formula: C35H53NaO8
Molecular Weight: 624.78
Percent Composition: C 67.28%, H 8.55%, Na 3.68%, O 20.49%
Properties: mp 176-178°. [a]D23 -82° (c = 0.2 in methanol). uv max (ethanol): 234, 270 nm (e 13000, 11000). pKa 1.8 ±0.3 (methanol/H2O 1:9). Sol in most organic solvents. Insol in water.
Melting point: mp 176-178°
pKa: pKa 1.8 ±0.3 (methanol/H2O 1:9)
Optical Rotation: [a]D23 -82° (c = 0.2 in methanol)
Absorption maximum: uv max (ethanol): 234, 270 nm (e 13000, 11000)
 
Therap-Cat-Vet: Ruminant performance enhancer.

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