[2R-[2α,3α(4E,7E)]]-3-(1-Oxonona-4,7-dienyl)oxiran-2-carboxamid

CERULENIN Struktur
17397-89-6
CAS-Nr.
17397-89-6
Bezeichnung:
[2R-[2α,3α(4E,7E)]]-3-(1-Oxonona-4,7-dienyl)oxiran-2-carboxamid
Englisch Name:
CERULENIN
Synonyma:
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
Summenformel:
C12H17NO3
Molgewicht:
223.27
MOL-Datei:
17397-89-6.mol

[2R-[2α,3α(4E,7E)]]-3-(1-Oxonona-4,7-dienyl)oxiran-2-carboxamid Eigenschaften

Schmelzpunkt:
93.5℃
alpha 
D16 +63° (c = 2 in methanol)
Siedepunkt:
bp 120° (10-8 mm)
Dichte
1.1223 (rough estimate)
Brechungsindex
1.5300 (estimate)
storage temp. 
−20°C
Löslichkeit
acetone: 20 mg/mL, clear, colorless to yellow
Aggregatzustand
White to off-white solid
pka
15.19±0.40(Predicted)
Farbe
Off-white
Merck 
13,2014
BRN 
4140423
Stabilität:
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.
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xn
R-Sätze: 22
S-Sätze: 24/25
WGK Germany  3
RTECS-Nr. JR1670000
10-21
HS Code  29419090
Toxizität LD50 in mice (mg/kg): 154 i.v.; 211 i.p.; 547 orally (Matsumae 1964)
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitsschädlich bei Verschlucken. Akute Toxizität oral Kategorie 4 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P270, P301+P312, P330, P501
Sicherheit
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P301+P312 BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P501 Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

[2R-[2α,3α(4E,7E)]]-3-(1-Oxonona-4,7-dienyl)oxiran-2-carboxamid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R22:Gesundheitsschädlich beim Verschlucken.

Beschreibung

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.

Chemische Eigenschaften

White powder

Verwenden

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.

Allgemeine Beschreibung

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.

läuterung methode

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.]

[2R-[2α,3α(4E,7E)]]-3-(1-Oxonona-4,7-dienyl)oxiran-2-carboxamid Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


[2R-[2α,3α(4E,7E)]]-3-(1-Oxonona-4,7-dienyl)oxiran-2-carboxamid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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17397-89-6([2R-[2α,3α(4E,7E)]]-3-(1-Oxonona-4,7-dienyl)oxiran-2-carboxamid)Verwandte Suche:


  • 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
  • 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
  • Crl
  • Glycerol Impurity 10
  • 17397-89-6
  • 17393-89-6
  • Antibiotics
  • Antibiotics A-F
  • Antibiotics A to Z
  • BioChemical
  • antibiotic
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