Cycloheximide

Description

Cycloheximide · CAS 4630-75-5 · C15H23NO4. UNII 98600C0908. Melting Point: 247 to 250 °F (EPA, 1998); Melting Point: 119.5-121 °C; also listed as 115-16 °C; Melting Point: 119.5-121 °C.

Identification

CAS Registry Number	4630-75-5
PubChem CID	6197
Molecular formula	C15H23NO4
IUPAC name	4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione
UNII (FDA)	98600C0908

Computed Descriptors

Molecular Weight	281.35
XLogP3	0.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	281.16270821
Monoisotopic Mass	281.16270821
Topological Polar Surface Area	83.5
Heavy Atom Count	20
Formal Charge	0

Physical & Chemical Properties

Melting Point	247 to 250 °F (EPA, 1998)
Melting Point	119.5-121 °C; also listed as 115-16 °C
Melting Point	119.5-121 °C
Solubility	10 to 50 mg/mL at 68 °F (NTP, 1992)
Solubility	In water, 2.1X10-4 mg/l @ 25 °C
Vapor Pressure	0.006 [mm Hg] @25 °C
LogP	log Kow = 0.55
LogP	0.55

Physical description & handling notes

• Cycloheximide appears as colorless crystals. Used as a fungicide and as a anticancer drug. (EPA, 1998)
• Colorless solid; [ICSC] White to beige powder; [MSDSonline]
• COLOURLESS CRYSTALS.
• Plates from amyl acetate, water or 30% methanol
• Crystals
• Glistening plates from methanol; mp: 148-149; specific optical rotation: +22 deg @ 25 °C/D (2.3% in methanol) /Cycloheximide acetate/

GHS Hazard Classification

Reported hazard statements	H300, H341, H411, H315 (38.4%), H360 (69.7%), H319

Documented Uses

• Antibiotic compound isolated from Streptomyces griseus; [Merck Index] Used as a fungicide, plant growth regulator, protein synthesis inhibitor, and to stimulate the natural abscission process (pre-harvest use on citrus); [HSDB]
• Fungicide; plant growth regulator; as protein synthesis inhibitor
• /Cycloheximide/ is used in laboratory media as a selective agent to permit isolation of pathogenic and non-pathogenic fungi from specimens such as sputa and feces which may be other fungi.
• Cycloheximide has a limited application in treatment of downy mildew of onions and shoot blight of Japanese larch.
• For more Uses (Complete) data for CYCLOHEXIMIDE (8 total), please visit the HSDB record page.
• Antibiotic substance isolated from beers of streptomycin-producing strains of Streptomyces griseus: Leach et al, J Am Chem Soc 69, 474 (1947); Ford, Leach, J Am Chem Soc 70, 1223 (1948); Whiffen et al, US patent 2,574,519 (1951 to Upjohn). Production, assay and antibiotic activity: Whiffen, J Bacteriol 56, 283 (1948). Improved production method: Kominek, US patents 3,915,802-3 (both 1975 to Upjohn). ... synthesis of dl- and l-forms: Johnson et al, J Am Chem Soc 88, 149 (1966).

Synonyms

cycloheximide; 66-81-9; ACTIDIONE; Cicloheximide; NARAMYCIN A; Actidion; Hizarocin; Naramycin; Kaken; Acti-Aid; Actidone; Neocycloheximide; Cicloheximida; Actispray; Acti-Dione; Actidione PM

Frequently Asked Questions

What are the CAS number and molecular formula of Cycloheximide?

CAS 4630-75-5; molecular formula C15H23NO4; molecular weight — g/mol.

What other names is Cycloheximide known by?

cycloheximide, 66-81-9, ACTIDIONE, Cicloheximide, NARAMYCIN A, Actidion.

Is Cycloheximide classified as hazardous?

Hazard statements reported: H300, H341, H411, H315, H360.

What are the key physical properties of Cycloheximide?

Melting Point: 247 to 250 °F (EPA, 1998); Melting Point: 119.5-121 °C; also listed as 115-16 °C; Melting Point: 119.5-121 °C; Solubility: 10 to 50 mg/mL at 68 °F (NTP, 1992).

Facts on this page are taken from PubChem (US National Library of Medicine) and Wikidata. Grade-specific data — assay, moisture, particle size, packaging, shelf life — is issued per batch on the COA and is not published here.