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Supelco

Cycloheximide

PESTANAL®, analytical standard

Synonym(s):

3-[2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide, Actidione, Naramycin A

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About This Item

Empirical Formula (Hill Notation):
C15H23NO4
CAS Number:
66-81-9
Molecular Weight:
281.35
Beilstein/REAXYS Number:
88868
EC Number:
200-636-0
MDL number:
MFCD00082346
UNSPSC Code:
41116107
PubChem Substance ID:
329757163
NACRES:
NA.24

grade

analytical standard

Quality Level

100

description

mixture of stereo isomers

product line

PESTANAL®

assay

≥95% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

solubility

H2O: slightly soluble

antibiotic activity spectrum

fungi

application(s)

agriculture
cleaning products
cosmetics
environmental
food and beverages
personal care

format

neat

mode of action

protein synthesis | interferes

storage temp.

−20°C

SMILES string

[H][C@]1(C[C@@H](C)C[C@H](C)C1=O)[C@H](O)CC2CC(=O)NC(=O)C2

InChI

1S/C15H23NO4/c1-8-3-9(2)15(20)11(4-8)12(17)5-10-6-13(18)16-14(19)7-10/h8-12,17H,3-7H2,1-2H3,(H,16,18,19)/t8-,9-,11-,12+/m0/s1

InChI key

YPHMISFOHDHNIV-FSZOTQKASA-N

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General description

Cycloheximide is an antibiotic having significant antifungal properties. It is produced by streptomycin-producing strains of Streptomyces griseus and acts by inhibiting protein synthesis. Its main biological activity is translation inhibition in eukaryotes resulting in cell growth arrest and cell death. It is used as a fungicide.
As per Regulation (EC) No 1107/2009, repealing the directive 91/414, cycloheximide is not approved for use in the European Union (EU).

Application

Cycloheximide may find the following uses:
  • To evaluate the antifungal efficacy and safety of cycloheximide as a supplement in Optisol-GS
  • To study the effect of cycloheximide on leaf-cutting ant workers
  • To study the effect of streptomycin, cycloheximide, fungizone, captan, carbofuran, cygon, and pentachloronitrobenzene on soil microorganisms
  • To study the fungal control of nitrous oxide production in a semiarid grassland
  • To study the activity and degradation of streptomycin and cycloheximide in soil

Biochem/physiol Actions

Mode of Action: Translation inhibition in eukaryotes resulting in cell growth arrest and cell death. CHX is widely used for the selection of CHX-resistant strains of yeast and fungi, controlled inhibition of protein synthesis for detection of short-lived proteins and super-induction of protein expression, and apoptosis induction or facilitation of apoptosis induction by death receptors.

Activity Spectrum: Active against yeast and fungi like Candida, Aspergillus, Saccharomyces, Penicillium

Legal Information

PESTANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Aquatic Chronic 2 - Muta. 2 - Repr. 1B

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM3154
BCCL9551
BCCL4263
BCCG8626
BCCG4773

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