CERULENIN
- CAS No.
- 17397-89-6
- Chemical Name:
- CERULENIN
- Synonyms
- Crl;CERULENIN;Nsc116069;Aids000236;helicocerin;Aids-000236;CERULENIN USP/EP/BP;Glycerol Impurity 10;Cerulenin (Synthetic);2,3-epoxy-4-oxo-10-dodecadienamide
- CBNumber:
- CB5355996
- Molecular Formula:
- C12H17NO3
- Molecular Weight:
- 223.27
- MOL File:
- 17397-89-6.mol
- MSDS File:
- SDS
- Modify Date:
- 2023/6/8 9:01:55
| Melting point | 93.5℃ |
|---|---|
| alpha | D16 +63° (c = 2 in methanol) |
| Boiling point | bp 120° (10-8 mm) |
| Density | 1.1223 (rough estimate) |
| refractive index | 1.5300 (estimate) |
| storage temp. | −20°C |
| solubility | acetone: 20 mg/mL, clear, colorless to yellow |
| form | White to off-white solid |
| pka | 15.19±0.40(Predicted) |
| color | Off-white |
| Merck | 13,2014 |
| BRN | 4140423 |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month. |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302 | |||||||||
| Precautionary statements | P264-P270-P301+P312-P501 | |||||||||
| Hazard Codes | Xn | |||||||||
| Risk Statements | 22 | |||||||||
| Safety Statements | 24/25 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | JR1670000 | |||||||||
| F | 10-21 | |||||||||
| HS Code | 29419090 | |||||||||
| Toxicity | LD50 in mice (mg/kg): 154 i.v.; 211 i.p.; 547 orally (Matsumae 1964) | |||||||||
| NFPA 704 |
|
CERULENIN price More Price(4)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | C2389 | Cerulenin ≥98% (HPLC), from Cephalosporium caerulens | 17397-89-6 | 5MG | ₹19084.48 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | C2389 | Cerulenin ≥98% (HPLC), from Cephalosporium caerulens | 17397-89-6 | 10MG | ₹34542.58 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | C2389 | Cerulenin ≥98% (HPLC), from Cephalosporium caerulens | 17397-89-6 | 50MG | ₹110393.35 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 219557 | Cerulenin, Cephalosporium caerulens - CAS 17397-89-6 - Calbiochem An antifungal antibiotic that inhibits sterol and fatty acid biosynthesis. | 17397-89-6 | 5MG | ₹13100 | 2022-06-14 | Buy |
CERULENIN Chemical Properties,Uses,Production
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.
Chemical Properties
White powder
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.
Definition
ChEBI: An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.
General Description
An anti-fungal antibiotic that inhibits fatty acid biosynthesis by binding, in equimolar ratio, to β-keto-acyl-ACP synthase. Also inhibits sterol synthesis by blocking the activity of HMG-CoA synthetase activity. Systemic and intracerebroventricular of this compound reduces feeding and induces weight loss.
Purification Methods
It forms white needles from *C6H6. It has also been purified by repeated chromatography through Florisil and silica gel. It is soluble in EtOH, MeOH, *C6H6, slightly soluble in H2O and pet ether. The dl-form has m 40-42o (from *C6H6/hexane), and the 2R,3S-tetrahydrocerulenin has m 86-87o, [] 20 +44.4 (c 0.25, MeOH after 24hours). [Ohrui & Emato Tetrahedron Lett 2095 1978, Sneda et al. Tetrahedron Lett 2039 1979, Broeckman & Thomas J Am Chem Soc 99 2805 1977, Jakubowski et al. J Org Chem 47 1221 1982, Beilstein 18/2 V 201.]
CERULENIN Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| career henan chemical co | +86-0371-86658258 +8613203830695 | China | 29824 | 58 | Inquiry |
| Shaanxi Dideu Medichem Co. Ltd | +86-029-81138252 +86-18789408387 | China | 3957 | 58 | Inquiry |
| Fuxin Pharmaceutical | +86-021-021-50872116 +8613122107989 | China | 10297 | 58 | Inquiry |
| SHANGHAI T&W PHARMACEUTICAL CO., LTD. | +86-021-61551413 +8618813727289 | China | 5738 | 58 | Inquiry |
| Hefei TNJ Chemical Industry Co.,Ltd. | +86-0551-65418671 +8618949823763 | China | 34571 | 58 | Inquiry |
| Shaanxi Dideu Medichem Co. Ltd | +86-029-89586680 +86-18192503167 | China | 8444 | 58 | Inquiry |
| BOC Sciences | 16314854226; +16314854226 | United States | 19743 | 58 | Inquiry |
| Henan Alfa Chemical Co., Ltd | +8618339805032 | China | 13183 | 58 | Inquiry |
| Shanghai Acmec Biochemical Technology Co., Ltd. | +undefined18621343501 | China | 33350 | 58 | Inquiry |
| Aladdin Scientific | +1-+1(833)-552-7181 | United States | 57511 | 58 | Inquiry |
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