Cerulenin

Base Information

• Chemical Name: Cerulenin
• CAS No.: 17397-89-6
• Molecular Formula: C₁₂H₁₇NO₃
• Molecular Weight: 223.272
• Hs Code.: 29419090
• European Community (EC) Number: 241-424-8
• UNII: MF286Y830Q
• ChEMBL ID: CHEMBL45627
• DSSTox Substance ID: DTXSID2040995
• Metabolomics Workbench ID: 43276
• Nikkaji Number: J9.098K
• Wikidata: Q5065296
• Wikipedia: Cerulenin
• Mol file: 17397-89-6.mol

Synonyms:2,3-Epoxy-4-oxo-7,10-dodecadienoylamide;Cerulenin

Chemical Property of Cerulenin

Chemical Property:

• Appearance/Colour: White to off-white powder.
• Vapor Pressure: 1.66E-08mmHg at 25°C
• Melting Point: 93.5℃
• Refractive Index: 1.529
• Boiling Point: 456.14 °C at 760 mmHg
• PKA: 15.19±0.40(Predicted)
• Flash Point: 241.135 °C
• PSA: 72.69000
• Density: 1.135 g/cm³
• LogP: 1.81110
• Storage Temp.: −20°C
• Solubility.: acetone: 20 mg/mL, clear, colorless to yellow
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 223.12084340
• Heavy Atom Count: 16
• Complexity: 320

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cerulenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• 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
• Description: Cerulenin is a fungal metabolite originally isolated from C. caerulens that has diverse biological activities. It is active against a variety of bacteria, including B. subtilis, E. coli, B. megaterium, and B. anthracis (MICs = 12.5, 12.5, 50, and 50 μg/ml, respectively) and fungi, including strains of C. albicans, T. rubrum, and A. fumigatus (MICs = 0.8-3.7, 3.1-6.2 and 12.5-50 μg/ml, respectively). Cerulenin is an inhibitor of fatty acid synthase type I (FAS-I) and FAS-II (IC50s = 3 and 20 μM, respectively, for the E. coli enzymes). It inhibits fatty acid synthesis in a panel of human cancer cell lines, including breast, ovarian, and endometrial cancer cells, as well as reduces tumor growth in a OVCAR-3 mouse xenograft model.
• Uses: Cerulenin is an epoxy fatty acid amide isolated from the fungus Cephalosporium caerulens and identified as an antifungal in the 1960s. Over the past 40 years, cerulenin has found broad application in lipid biochemistry as an inhibitor fatty acid and sterol biosynthesis. Cerulenin binds to β-keto-acyl-ACP synthase blocking the interaction of malonyl CoA. Cerulenin also an inhibits bacterial fatty acid synthesis, acting on the FabH, FabB and FabF condensation enzymes. Cerulenin stimulates fatty acid oxidation and inhibits HMG-CoA synthetase activity. Cerulenin is an epoxy fatty acid amide isolated from the fungus Cephalosporium caerulens identified as an antifungal in the 1960s. Over the past 40 years, cerulenin has found broad application in lipid biochemistry as an inhibitor fatty acid and sterol biosynthesis. Cerulenin binds to β-keto-acyl-ACP synthase blocking the interaction of malonyl CoA. Cerulenin also an inhibits bacterial fatty acid synthesis, acting on the FabH, FabB and FabF condensation enzymes. Cerulenin stimulates fatty acid oxidation and inhibits HMG-CoA synthetase activity. Cerulenin is used as an antifungal antibiotic that inhibits sterol and fatty acids biosynthesis. Cerulenin induces apoptosis in tumor cell lines. It can be a useful biochemical tool with applications for the study of metabolism and function of fatty acids in the bacterial cell membrane and in yeast. An extensive review including the properties, uses, mechanism of action and structure has been reported.

Technology Process of Cerulenin

There total 10 articles about Cerulenin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

(2R,3R)-3-[(1R,4E,7E)-1-hydroxy-4,7-nonadienyl]-2-oxiranecarboxamide (72301-02-1) → cerulenin (62964-96-9,68926-46-5,17397-89-6)

Guidance literature:

With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jo9618177

Reference yield: 63.0%

(2R,3R,4S)-2,3-epoxy-4-hydroxy-7,10-(E,E)-dodecadienamide (139407-04-8) → cerulenin (62964-96-9,68926-46-5,17397-89-6)

Guidance literature:

With sodium acetate; pyridinium chlorochromate; In dichloromethane;

DOI:10.1016/S0040-4039(00)93599-8

Reference yield:

(1R,4S,5S)-4-Ethoxy-4-((3E,6E)-octa-3,6-dienyl)-3,6-dioxa-bicyclo[3.1.0]hexan-2-one (180153-10-0) → cerulenin (62964-96-9,68926-46-5,17397-89-6)

Guidance literature:

With ammonia; In diethyl ether; at 0 ℃; for 2.5h; Yield given;

DOI:10.1021/jo960664k

upstream raw materials:

(2R,3R,4S)-2,3-epoxy-4-hydroxy-7,10-(E,E)-dodecadienamide

(2R,3R)-3-[(1R,4E,7E)-1-hydroxy-4,7-nonadienyl]-2-oxiranecarboxamide

(1R,4S,5S)-4-Ethoxy-4-((3E,6E)-octa-3,6-dienyl)-3,6-dioxa-bicyclo[3.1.0]hexan-2-one

(S)-5-But-3-enyl-5-ethoxy-5H-furan-2-one

Refernces

• 1、 Renard, Marc,Ghosez, Léon A.. "A convergent asymmetric synthesis of γ-butenolides". . p. 2597 - 2608. Retrieved 2007/10/03.
• 2、 Morisaki,Funabashi,Furukawa,Shimazawa,Kanematsu,Ando,Okuda,Iwasaki. "Syntheses of cerulenin and its analogs. I. Cerulenin and its analogs with modified side chain". . p. 2945 - 2953. Retrieved 2007/10/02.