Cerulenin
Molecular Formula
C12H17NO3
M.W.
223.27
CAS number
17397-89-6
MSDS
Source
Cephalosporium caerulens
Fermentek product Code
CER-001
Brand/grade
For research
Appearance
White to off white powder
Purity by HPLC
≥98% ; refer to CoA for more data
Purity By TLC
≥98% ; refer to CoA for more data
Solubility test
Clear colorless solution at 5mg/ml of Dichloromethane
Names and identifiers

Synonyms

  • Cerulenin
  • Helicocerin

IUPAC Name: (2R,3S)-3-[(4E,7E)-Nona-4,7-dienoyl]oxirane-2-carboxamide

Systematic name: (2R,3S)-3-[(4E,7E)-4,7-Nonadienoyl]-2-oxiranecarboxamide

RTECS: JR1670000

EU number
241-424-8
Chemical name
7,10-Dodecadienamide, 2,3-epoxy-4-oxo-
Description

Cerulenin: an antifungal antibiotic, fatty acids and sterols biosynthesis inhibitor.

InChl Key
GVEZIHKRYBHEFX-NQQPLRFYSA-N
Canonical SMILES
CC=CCC=CCCC(=O)C1C(O1)C(=O)N
Isomeric SMILES
C/C=C/C/C=C/CCC(=O)[C@@H]1[C@@H](O1)C(=O)N
Solubility ( literature )

Cerulenin is soluble in DMSO, Methanol, Ethanol, Dichloromethane, Acetone, Benzene and most common solvents. Concentrations up to 20 mg/ml can be achieved. Slightly soluble in H2O. Concentrations up to 0.2 mg/ml are achievable.Not soluble in Petrol Ether.Attention: Cerulenin is unstable in aqueous solutions, and very unstable in basic solutions

Compound Classification

 

  • Fatty acid antibiotic.
  • Apoptosis inducer
  • Antifungal antibiotic
  • Mycobacteria inhibitor
Storage, handling
Store in a freezer upon arrival, at -10°C to -25°C
Use the original container to store the product.
Keep the lid tightly closed.
Applications

Cerulenin was originally proposed as antifungal antibiotic. Cerulenin is used as a biochemical tool. Cerulenin has been shown to cause dramatic weight loss in animals. Cerulenin blocks synthesis of fatty acids and sterols by binding to the enzyme fatty-acid-synthase. In some tumor lines, this triggers apoptosis., an effect believed to be mediated by the accumulation of malonyl-coenzyme A in cells with an upregulated FAS pathway.

Disclaimer
For Research use only
Not for Human or Drug use
Not extracted from humans or animals
Refer to MSDS for further safety and handling instructions
Ingredient type
Fermentek product
Available since
Title
Oral Toxicity Mouse
Value
547 mg/kg ; category 4
Title
Deleted CAS Numbers
Value
11052-24-7; 23557-85-9
Title
Transport information
Value
Not regulated/not hazardous
Title
stability comments
Value
in higher pH, not stable. use some acidifier
Signal to sort
C