Cycloheximide

Base Information

• Chemical Name: Cycloheximide
• CAS No.: 66-81-9
• Deprecated CAS: 17974-04-8,4630-76-6,6399-67-3
• Molecular Formula: C15H23NO4
• Molecular Weight: 281.352
• Hs Code.: 29419000
• European Community (EC) Number: 200-636-0
• ICSC Number: 0244
• NSC Number: 758187,185
• UN Number: 2588
• UNII: 98600C0908
• DSSTox Substance ID: DTXSID6024882
• Nikkaji Number: J107.994H
• Wikipedia: Cycloheximide
• Wikidata: Q412895
• NCI Thesaurus Code: C171712
• Pharos Ligand ID: LJHWJX8XBGWD
• Metabolomics Workbench ID: 51400
• ChEMBL ID: CHEMBL123292
• Mol file: 66-81-9.mol

Synonyms:Actidione;Cicloheximide;Cycloheximide

Chemical Property of Cycloheximide

Chemical Property:

• Appearance/Colour: Off-white to light tan powder
• Vapor Pressure: 9.81E-12mmHg at 25°C
• Melting Point: 111-116 °C
• Refractive Index: 1.498
• Boiling Point: 491.8 °C at 760 mmHg
• PKA: 11.61±0.40(Predicted)
• Flash Point: 251.2 °C
• PSA: 83.47000
• Density: 1.136 g/cm³
• LogP: 1.37030
• Storage Temp.: 2-8°C
• Solubility.: Soluble in Ethanol (up to 14 mg/ml) or in Water (up to 7 mg/ml).
• Water Solubility.: 2.1 g/100 mL (2 ºC)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 281.16270821
• Heavy Atom Count: 20
• Complexity: 404
• Transport DOT Label: Poison

Purity/Quality:

99%, ^*data from raw suppliers

Cycloheximide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T, N, T+
• Hazard Codes: Xn,T,N,T+
• Statements: 22-68-61-51/53-28-38-52/53
• Safety Statements: 53-45-61-36/37-28

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Plant Growth Regulators
• Canonical SMILES: CC1CC(C(=O)C(C1)C(CC2CC(=O)NC(=O)C2)O)C
• Isomeric SMILES: C[C@H]1C[C@@H](C(=O)[C@@H](C1)[C@@H](CC2CC(=O)NC(=O)C2)O)C
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly.
• Effects of Short Term Exposure: The substance is irritating to the eyes and skin. Exposure could cause death.
• Description: Cycloheximide is a glutarimide-type antibiotic produced by Streptomyces griseus. Colorless crystals, C15H23NO4 (281.4), melting point: 115.5–117 ?C, weak acidic substance (pKa 11.2), Soluble in chloroform, isopropanol and methanol; water > 21 g/L (2 ?C). Stable in pH 3–5, but rapidly destroyed in alkaline solutions. Cycloheximide is a glutarimide antibiotic produced by S. griseus that inhibits protein synthesis in eukaryotes (IC50 = 5-50 μM) by interfering with translational elongation. Its effects on protein synthesis can either induce or inhibit apoptosis depending on cell type. Cycloheximide is widely used as a tool in molecular biology research for ribosome profiling and translational profiling as well as to determine the half-life of a protein.
• Uses: immunomodulator Cycloheximide is an antibiotic substance isolated from the beers of streptomycin-producing strains of Streptomyces griseus. Cycloheximide is used as fungicide. Cycloheximide is the most recognised member of the glutarimide microbial metabolites. Cycloheximide was isolated from Streptomyces griseus in the late 1940s as a potent and broad spectrum antifungal. Cycloheximide inhibits protein synthesis by interfering with translocation. Cycloheximide is an established bioprobe and widely-used antifungal reagent in research with over 25,000 literature citations. potent and selective 5-HT uptake inhibitor

Technology Process of Cycloheximide

There total 25 articles about Cycloheximide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C29H45NO5Si → Cycloheximide (66-81-9)

Guidance literature:

With ammonium cerium (IV) nitrate; In water; acetonitrile; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.201901386

Reference yield:

(2,6-dioxo-piperidin-4-yl)-acetaldehyde (2066-88-8) + (+)-(2S,4R)-trans-2,4-dimethyl-1-cyclohexanone (93921-42-7) → (2S,4S,6R,αS)-cycloheximide (94130-63-9) + (2S,4S,6S,αS)-cycloheximide (66-81-9,642-81-9,1154-57-0,3226-22-0,4630-75-5,5549-69-9,6258-25-9,6746-42-5,17280-60-3,17973-87-4,18006-33-2,29106-61-4,94130-62-8,94130-63-9,94799-82-3,95272-16-5,95272-17-6,95272-18-7) + Cycloheximide (642-81-9) + Cycloheximide (66-81-9)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -70 ℃; for 0.5h; Yield given. Yields of byproduct given;

DOI:10.1271/bbb1961.48.2315

Reference yield:

(2,6-dioxo-piperidin-4-yl)-acetaldehyde (2066-88-8) + (+)-(2S,4R)-trans-2,4-dimethyl-1-cyclohexanone (93921-42-7) → (2S,4S,6R,αS)-cycloheximide (94130-63-9) + (2S,4S,6S,αS)-cycloheximide (66-81-9,642-81-9,1154-57-0,3226-22-0,4630-75-5,5549-69-9,6258-25-9,6746-42-5,17280-60-3,17973-87-4,18006-33-2,29106-61-4,94130-62-8,94130-63-9,94799-82-3,95272-16-5,95272-17-6,95272-18-7) + Cycloheximide (642-81-9) + Cycloheximide (66-81-9)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -70 ℃; for 0.5h; Yield given. Yields of byproduct given;

DOI:10.1271/bbb1961.48.2315

upstream raw materials:

(2,6-dioxo-piperidin-4-yl)-acetaldehyde

(+)-(2S,4R)-trans-2,4-dimethyl-1-cyclohexanone

dehydrocycloheximide

3-[(dodecylthio-carbonyl)-methyl]-glutarimide

Downstream raw materials:

(+)-(2S,4R)-trans-2,4-dimethyl-1-cyclohexanone

3-[2-(2-hyroxy-3,5-dimethylphenyl)-2-oxoethyl] glutarimide

(2S,4S,6R,αS)-cycloheximide

(2S,4S,6S,αS)-cycloheximide

Refernces

• 1、 Yin, Min,Yan, Yijun,Lohman, Jeremy R.,Huang, Sheng-Xiong,Ma, Ming,Zhao, Guang-Rong,Xu, Li-Hua,Xiang, Wensheng,Shen, Ben. "Cycloheximide and actiphenol production in streptomyces sp. YIM56141 governed by single biosynthetic machinery featuring an acyltransferase-less type i polyketide synthase". supporting information. p. 3072 - 3075. Retrieved 2014/06/23.
• 2、 Kudo,Oritani,Yamashita. "Synthesis and antimicrobial activity of optically active trans-cycloheximide isomers". . p. 2315 - 2319. Retrieved 2007/10/02.