Cerulenin

Molecular Formula

C12H17NO3

M.W.

223.27

CAS number

17397-89-6

MSDS

Download

Details

Source

Cephalosporium caerulens

Fermentek product Code

CER-001

Brand/grade

For research

Specifications

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

Chemical identification

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

Further Information

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.

Retest time

3 Years

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

Composition

Ingredient type

Fermentek product

Special Info

Available since

1998