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Cerulenin (CAS 17397-89-6)

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Synonym:3-(nona-4,7-dienoyl)oxirane-2-carboxamide
Application:An antibiotic fatty acid synthase (FAS) inhibitor
CAS Number:17397-89-6
Purity:≥98%
Molecular Weight:223.27
Molecular Formula:C12H17NO3
Refer to Certificate of Analysis for lot specific data (including water content).
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 Ordering Information
Product NameCatalog #UnitPriceQtyAddFavorites
Cerulenin sc-200827 5 mg $89
Cerulenin sc-200827A 10 mg $167
Description
Cerulenin is an antibiotic and antifungal agent originally isolated from Cephalosporium caerulens. The compound acts as a potent and specific Fatty Acid Synthase (FAS) inhibitor and has been shown to block the synthesis of stearoyl-CoA and eicosanoyl-CoA fatty acids in microsomes. Cerulenin binds covalently to the active center cysteine of the condensing enzyme domain and inhibits the FAS. Leptin and Cerulenin have both been reported to affect the rate of metabolism in mice independent of the melanocortin system, with the difference being that cerulenin does not inhibit the neuroendocrine effects of fasting in mice. Mitochondrial investigations indicate that cerulenin induces apoptosis in a caspase-dependent manner in A-375 cells.
Technical Information
Physical State:Solid
Derived from:synthetic
Solubility:Soluble in ethanol (~20 mg/ml), benzene, 1:6 DMF:PBS (~0.2 mg/ml), DMSO (~25 mg/ml), DMF (~30 mg/ml), dichloromethane (5 mg/ml), and acetone.
Storage:Store at -20° C
Melting Point:93 °C
Boiling Point:120 °C
Density:1.14 g/cm3
Refractive Index:n20D 1.53
IC50:β-keto-acyl-ACP synthase: IC50 = 1.5 µM
Safety and Reference Information
WGK Germany:3
RTECS:JR1670000
PubChem CID:5352018
Merck Index:14: 2004
MDL Number:MFCD00077686
EC Number:241-424-8
Beilstein Registry:4140423
SMILES:C/C=C/C/C=C/CCC(=O)[C@@H]1[C@@H](O1)C(=O)N
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
References
1. Schneider, F., et al. 1993. Biochim. Biophys. Acta. 1152: 243-252. PMID: 8218325
2. Inokoshi, J., et al. 1994. Mol. Gen. Genet. 244: 90-96. PMID: 8041367
3. Makimura, H., et al. 2001. Diabetes. 50: 733-739. PMID: 11289036
4. Heiligtag, S.J., et al. 2002. Cell Death Differ. 9: 1017-1025. PMID: 12181752
5. Ho, T.S., et al. 2007. Biomed. Pharmacother. 61: 578-587. PMID: 17904792
6. Murata, S., et al. 2010. Cancer Sci. 101: 1861-1865. PMID: 20491775
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