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CERULENIN

Product Name
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
Formula Weight
223.27
MOL File
17397-89-6.mol
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CERULENIN Property

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
pka
15.19±0.40(Predicted)
form 
White to off-white solid
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.
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C2389
Product name
Cerulenin
Purity
≥98% (HPLC), from
Packaging
5mg
Price
$160
Updated
2024/03/01
Sigma-Aldrich
Product number
219557
Product name
Cerulenin
Packaging
5mg
Price
$144
Updated
2024/03/01
Alfa Aesar
Product number
J64538
Product name
Cerulenin, 98%
Packaging
5mg
Price
$159
Updated
2024/03/01
Alfa Aesar
Product number
J64538
Product name
Cerulenin, 98%
Packaging
10mg
Price
$349
Updated
2024/03/01
Cayman Chemical
Product number
10005647
Product name
Cerulenin
Purity
≥98%
Packaging
5mg
Price
$110
Updated
2024/03/01
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CERULENIN Chemical Properties,Usage,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.

Uses

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.

Uses

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.

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.

Biochem/physiol Actions

Primary Targetsterol & fatty acid biosynthesis

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.]

References

1) Yasuno et al. (2004), Identification and molecular characterization of the beta-ketoacyl-[acyl carrier protein] synthase component of the Arabidopsis mitochondrial fatty acid synthase; J. Biol. Chem., 279 8242 2) Makimura et al. (2001), Cerulenin mimics effects of leptin on metabolic rate, food intake, and body weight independent of the melanocortin system, but unlike leptin, cerulenin fails to block neuroendocrine effects of fasting; Diabetes, 50 733 3) Metz et al. (1993), Modulation of insulin secretion from normal rat islets by inhibitors of the post-translational modifications of GTP-binding proteins; Biochem. J., 295 31 4) Ho et al. (2007), Fatty acid synthase inhibitors cerulenin and C75 retard growth and induce caspase-dependent apoptosis in human melanoma A-375 cells; Biomed. Pharmacother., 61 578

CERULENIN Preparation Products And Raw materials

Raw materials

Preparation Products

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CERULENIN Suppliers

Australia 1 China 97 Germany 4 Japan 2 South Korea 1 Switzerland 3 United Kingdom 9 United States 23 Global 140
J & K SCIENTIFIC LTD.
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View Lastest Price from CERULENIN manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
Cerulenin 17397-89-6
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20T
Release date
2020-05-09
Career Henan Chemical Co
Product
CERULENIN 17397-89-6
Price
US $1.00/g
Min. Order
1g
Purity
≥98%
Supply Ability
g/kg/Ton
Release date
2019-12-25

17397-89-6, CERULENINRelated Search:

Simvastatin 1,6-BIS(CYCLOHEXYLOXIMINOCARBONYLAMINO)HEXANE Fatostatin A 6-ISOPROPOXY-9-XANTHONE-2-CARBOXYLIC ACID Phytosphingosine C2 DIHYDROCERAMIDE Ginkgolide B 1-[[4-[(4-Fluoro-2-methyl-1H-indol-5-yl)oxy]-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl]oxy]-2-propanol 5 MG CERULENIN FROM CEPHALOSPORIUMCAERULENS, RESEARCH GRADE CERULENIN GLYCIDAMIDE 2,3-EPOXYHEPTANAL 2-ACETYLOXIRANE

  • CERULENIN FROM CEPHALOSPORIUM CAERULENS
  • [2R-[2.alpha.,3.alpha.(4E,7E)]]-3-(1-Oxo-4,7-nonadienyl)oxiranecarboxamide
  • 2,3-EPOXY-4-OXO-7,10-DODECADIENAMIDE
  • (2R,3S,E,E)-2,3-EPOXY-4-OXO-7,10-DODECADIENAMIDE
  • 2R,3S-EPOXY-4-OXO-7,10-DODECADIENAMIDE
  • [2R-[2alpha,3alpha(4E,7E)]]-3-(1-oxonona-4,7-dienyl)oxirane-2-carboxamide
  • 2,3-epoxy-4-oxo-10-dodecadienamide
  • 3-(1-oxo-4,7-nonadienyl)-,(2r-(2-alpha,3-alpha(4e,7e)))-oxiranecarboxamid
  • 3-(1-oxo-4,7-nonadienyl)oxiranecarboxamide
  • helicocerin
  • CERULENIN
  • CERULENIN, CEPHALOSPORIUM CAERULENS
  • Aids000236
  • Aids-000236
  • Crl
  • Nsc116069
  • Cerulenin,(2R,3S,E,E)-2,3-Epoxy-4-oxo-7,10-dodecadienamide
  • (2r,3s)-2,3-epoxy-4-oxo-7e,10e-dodecadienamide
  • (2s)(3r)-2,3-epoxy-4-oxo-7,10-dodecadienoylamide
  • Helicocerin, NSC 116069, 2,3-Epoxy-4-oxo-7,10-dodecadienaMide
  • (2R,3S)-3-[(4E,7E)-1-Oxo-4,7-nonadien-1-yl]-2-oxiranecarboxamide
  • 2-Oxiranecarboxamide,3-[(4E,7E)-1-oxo-4,7-nonadien-1-yl]-, (2R,3S)-
  • Cerulenin/ Helicocerin / (2R,3S)-3-[(4E,7E)-1-Oxo-4,7-nonadien-1-yl]-2-oxiranecarboxamide
  • Cerulenin (Synthetic)
  • Cerulenin, Cephalosporium caerulens - CAS 17397-89-6 - Calbiochem
  • CERULENIN USP/EP/BP
  • Glycerol Impurity 10
  • 17397-89-6
  • 17393-89-6
  • Antibiotics
  • Antibiotics A-F
  • Antibiotics A to Z
  • BioChemical
  • antibiotic