Structural Formula Vector Image
Title: Cycloheximide
CAS Registry Number: 66-81-9
CAS Name: 4-[(2R)-2-[(1S,3S,5S)-3,5-Dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]-2,6-piperidinedione
Additional Names: 3-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide; actidione; naramycin A
Manufacturers' Codes: NSC-185; U-4527
Molecular Formula: C15H23NO4
Molecular Weight: 281.35
Percent Composition: C 64.03%, H 8.24%, N 4.98%, O 22.75%
Literature References: Antibiotic substance isolated from the beers of streptomycin-producing strains of Streptomyces griseus: B. E. Leach et al., J. Am. Chem. Soc. 69, 474 (1947); J. H. Ford, B. E. Leach, ibid. 70, 1223 (1948); A. J. Whiffen et al., US 2574519 (1951 to Upjohn). Production, assay and antibiotic activity: A. J. Whiffen, J. Bacteriol. 56, 283 (1948). Improved production method: Kominek, US 3915802; US 3915803 (both 1975 to Upjohn). Structure: E. C. Kornfeld et al., J. Am. Chem. Soc. 71, 150 (1949). Absolute configuration: E. J. Eisenbraun et al., ibid. 80, 1261 (1958); F. Johnson, N. A. Starkovsky, Tetrahedron Lett. 1962, 1173; F. Johnson et al., J. Am. Chem. Soc. 87, 4612 (1965). Synthesis of dl- and l-forms: F. Johnson et al., ibid. 88, 149 (1966).
Properties: Plates from amyl acetate or water or 30% methanol, mp 119.5-121° (Whiffen, 1951); also reported as mp 115-116° (Johnson, 1966). [a]D29 -3.38° (c = 9.47 in methanol); [a]D25 +6.8° (c = 2 in H2O). Soly at 2°: water 2.1 g/100 ml, amyl acetate 7 g/100 ml. Also sol in chloroform, ether, acetone, methanol, ethanol, other common organic solvents except satd hydrocarbons. Relatively heat-stable, acid-stable, destroyed by boiling in aq soln at pH 7 for 1 hr, but shows no loss of activity after 15 min boiling. At pH 2 it is not destroyed by boiling for 1 hr. Rapidly inactivated at room temp by dil alkali with the formation of a volatile, fragrant ketone, 2,4-dimethylcyclohexanone. Extremely repellent to rats. LD50 i.v. in mice: 150 mg/kg (Leach).
Melting point: mp 119.5-121° (Whiffen, 1951); mp 115-116° (Johnson, 1966)
Optical Rotation: [a]D29 -3.38° (c = 9.47 in methanol); [a]D25 +6.8° (c = 2 in H2O)
Toxicity data: LD50 i.v. in mice: 150 mg/kg (Leach)
Derivative Type: Acetate
Molecular Formula: C17H25NO5
Molecular Weight: 323.38
Percent Composition: C 63.14%, H 7.79%, N 4.33%, O 24.74%
Properties: Glistening plates from methanol, mp 148-149°. [a]D25 +22° (c = 2.3 in methanol).
Melting point: mp 148-149°
Optical Rotation: [a]D25 +22° (c = 2.3 in methanol)
Use: Fungicide; plant growth regulator. As protein synthesis inhibitor.

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