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7(S),20(R)-Dihydroxy-16(R)-methyl-10-phenyl-24-oxa(14)cytochalasa-6(12),13(E),21(E)-trien-1,23-dion

CYTOCHALASIN B Struktur
14930-96-2
CAS-Nr.
14930-96-2
Bezeichnung:
7(S),20(R)-Dihydroxy-16(R)-methyl-10-phenyl-24-oxa(14)cytochalasa-6(12),13(E),21(E)-trien-1,23-dion
Englisch Name:
CYTOCHALASIN B
Synonyma:
cytochalasin;PHOMIN;-23-one;CYTOCHALACINB;CYTOCHALICINB;CYTOCHALASIN B;CYTOCHALASIN B(RG);Cytochalasin B (Phomin);CYTOCHALASIN B USP/EP/BP;(7s,13e,16r,20r,21e)-0-phenyl
CBNumber:
CB6323824
Summenformel:
C29H37NO5
Molgewicht:
479.61
MOL-Datei:
14930-96-2.mol

7(S),20(R)-Dihydroxy-16(R)-methyl-10-phenyl-24-oxa(14)cytochalasa-6(12),13(E),21(E)-trien-1,23-dion Eigenschaften

Schmelzpunkt:
218-223 °C
Siedepunkt:
577.96°C (rough estimate)
Dichte
1.1490 (rough estimate)
Brechungsindex
1.6290 (estimate)
Flammpunkt:
85℃
storage temp. 
-20°C
L?slichkeit
ethanol: 20 mg/mL
Aggregatzustand
powder
pka
13.60±0.70(Predicted)
Farbe
white
Merck 
13,2819
BRN 
1096207
Stabilit?t:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
InChIKey
UXVDBQLLXVKPRS-UZBFCAAUSA-N
LogP
3.370
EPA chemische Informationen
Cytochalasin B (14930-96-2)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher T+,T
R-S?tze: 26/27/28-63-23/24/25
S-S?tze: 28-36/37-45
RIDADR  UN 1544 6.1/PG 2
WGK Germany  3
RTECS-Nr. RO0205000
10
HazardClass  6.1(a)
PackingGroup  I
HS Code  29349990
Giftige Stoffe Daten 14930-96-2(Hazardous Substances Data)
Toxizit?t LD50 intraperitoneal in mouse: 30mg/kg
Bildanzeige (GHS) GHS hazard pictogramsGHS hazard pictograms
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H361 Kann vermutlich die Fruchtbarkeit beeintr?chtigen oder das Kind im Mutterleib sch?digen. Reproduktionstoxizit?t Kategorie 2 Warnung P201, P202, P281, P308+P313, P405,P501
Sicherheit
P201 Vor Gebrauch besondere Anweisungen einholen.
P202 Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.
P260 Dampf/Aerosol/Nebel nicht einatmen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

7(S),20(R)-Dihydroxy-16(R)-methyl-10-phenyl-24-oxa(14)cytochalasa-6(12),13(E),21(E)-trien-1,23-dion Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R26/27/28:Sehr giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R63:Kann das Kind im Mutterleib m?glicherweise sch?digen.
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.

S-S?tze Betriebsanweisung:

S28:Bei Berührung mit der Haut sofort abwaschen mit viel . . . (vom Hersteller anzugeben).
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).

Chemische Eigenschaften

white to off-white powder

Verwenden

Cytochalasin B is one of the most extensively studied members of a family of potent mycotoxins produced by several species of fungi. All members of the class exhibit profound effects on cytoskeletal proteins, giving rise to pronounced morphogenic activity in animals and plants. Like most cytochalsins, cytochalasin B exhibits potent inhibition of actin filament function leading to cell death by apoptosis, and displays a broad range of resultant cellular actions. Despite the common mode of action, there is evidence that individual members of this class display diverse selectivity. However, lack of comparative co-metabolite analysis has restricted a more complete understanding of their individual selectivity.

Definition

ChEBI: An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments.

Allgemeine Beschreibung

Cytochalasin B is a cell-permeable fungal toxin / mycotoxin that binds to the ′barbed′ end of actin / actin filaments. This binding leads to:
  • Disruption of actin filaments and of interaction of actin filaments in solution
  • Inhibition of actin polymerization
  • Inhibition of subunit association and dissociation
Cytochalasin B is widely used in studies of glucose transporters (GLUT). Cytochalasin B is also used as an integral part of various in vitro micronucleus assay protocols.

l?uterung methode

Purify it by MeOH extraction, reverse phase C18 silica gel batch extraction by selective elution with 1:1 v/v hexane/tetrahydrofuran, crystallisation, subjected to TLC and recrystallisation [Lipski et al. Anal Biochem 161 332 1987]. It is soluble in EtOH (3.6%), Me2CO (1%), Me2SO (37%) and Me2NCHO (49%) at 24o, and can be crystallised from the first two solvents. It interferes with cellular movement [Korm Physiol Reviews 62 672 1982].

7(S),20(R)-Dihydroxy-16(R)-methyl-10-phenyl-24-oxa(14)cytochalasa-6(12),13(E),21(E)-trien-1,23-dion Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


7(S),20(R)-Dihydroxy-16(R)-methyl-10-phenyl-24-oxa(14)cytochalasa-6(12),13(E),21(E)-trien-1,23-dion Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

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14930-96-2(7(S),20(R)-Dihydroxy-16(R)-methyl-10-phenyl-24-oxa(14)cytochalasa-6(12),13(E),21(E)-trien-1,23-dion)Verwandte Suche:


  • CytochalasinB from Drechslera dematioidea,Phomin
  • Cytochalasin B, froM Drechslera deMatoidea
  • Cytochalasin B (7S),(20R)-Dihydroxy-16(R)-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13(E),21(E)-triene-1,23-dione
  • Cytochalasin B from Helminthosporium dematioideum
  • ec[2,3-d]isoindole-2,18(5h)-dione
  • (E,E)-16-BENZYL-6,7,8,9,10,12A,13,14,15,15A,16,17-DODECAHYDRO-5,13-DIHYDROXY-9,15-DIMETHYL-14-METHYLENE-2H-OXACYCLOTETRADE[2,3-D]ISOINDOLE-2,18(5H)-DIONE
  • CYTOCHALASIN B, HELMINTHOSPORIUM DEMATIOIDEUM
  • CYTOCHALASIN B
  • ,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-,(e,e)
  • ,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-2h-oxacyclotetrad
  • -23-one
  • 24-oxa(14)cytochalasa-6(12),13,21-triene-1,23-dione,7,20-dihydroxy-16-methyl-1
  • 2h-oxacyclotetradec(2,3-d)isoindole-2,18(5h)-dione,16-benzyl-6,7,8,9,10,12a,13
  • 3-d)isoindole-2,18(5h)-dione,16-benzyl-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-2h-oxacyclotetradec(
  • 7,20-dihydroxy-10-phenyl-5,16-dimethyl-24-oxa-[14]cytochalas-6(12),13,21-trien
  • 7(S),20(R)-dihydroxy-16(R)-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13(E),21(E)-triene-1,23-dione
  • Cytochalasin beta,helminthosporium dematioideum
  • cytochalasin b from drechslera dematioidea
  • CYTOCHALASIN B(RG)
  • CYTOCHALACINB
  • CYTOCHALICINB
  • CYTOCHALASIN B FROM HELMINTHOSPORIUM DEMATIODEUM
  • (7S,13E,16R,20R,21E)-7,20-Dihydroxy-16-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13,21-triene-1,23-dione
  • (7S),(20R)-Dihydroxy-16(R)-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13(E),21(E)-triene-1,23-dione
  • (7s,13e,16r,20r,21e)-0-phenyl
  • (e,e)-(5s,9r,12as,13s,15s,15as,16s,18as)-16-benzyl-6,7,8,9,10,12a,13,14,15,15a
  • ,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-,(e)-(
  • 9r,12as,13s,15s,15as,16as,18as)-5
  • 9r,12as,13s,15s,15as,16s,18as)--(5
  • CYTOCHALASIN B FROM DRESCHSLERA DEMATIOIDEA
  • CYTOCHALASIN B SYNTHETIC >97%
  • CYTOCHALASIN B FROM DRESCHSLERA DEMATIOIDEA, BIOCHEMIKA, >= 95.0% (HPLC)
  • Cytochalasin B, Helminthosporium dematioideum - CAS 14930-96-2 - Calbiochem
  • (3E,5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-6,7,8,9,10,12a,13,14,15,15a,16,17-Dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-2H-oxacyclotetradecino[2,3-d]isoindole-2,18(5H)-dione
  • Cytochalasin B (Phomin)
  • Cytochalasin B (Synonyms: Phomin)
  • Cytochalasin B, 98%, from Drechslera dematoidea
  • 2H-Oxacyclotetradecino[2,3-d]isoindole-2,18(5H)-dione,6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-,(3E,5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-
  • CYTOCHALASIN B USP/EP/BP
  • 16-benzyl-5,13-dihydroxy-9,15-dimethyl-14-methylidene-2H,5H,6H,7H,8H,9H,10H,12aH,13H,14H,15H,15aH,16H,17H,18H-oxacyclotetradeca[3,2-e]isoindole-2,18-dione
  • cytochalasin
  • PHOMIN
  • 14930-96-2
  • C29H37NO5
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