Cerulenin

Molecular Formula:

C12H17NO3

CAS number:

17397-89-6

EU number:

241-424-8

Fermentek product code:

CER

Source:

Cephalosporium caerulens

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

Chemical name:

7,10-Dodecadienamide, 2,3-epoxy-4-oxo-

Description:

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

Molecular weight:

223.27

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)[[email protected]@H]1[[email protected]@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.

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

Other Fields

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

Cerulenin

Specifications

Chemical identification

Further Information

Composition

Special Info

Other Fields

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