36011-19-5

Basic information

• Product Name: CYTOCHALASIN E
• Synonyms: (7S,13E,16S,18R,19E)-6,7-Epoxy-18-hydroxy-16,18-dimethyl-10-phenyl-21,23-dioxa[13]cytochalasa-13,19-diene-1,17,22-trione;[7β,13E,16S,18R,19E]-6,7-Epoxy-18-hydroxy-16,18-dimethyl-10-phenyl-21,23-dioxa[13]cytochalasa-13,19-diene-1,17,22-trione;(7s,13e,16s,18r,19e)-18-dimethyl-10-phenyl;21,23-dioxa(13)cytochalasa-13,19-diene-1,17,22-trione,6,7-epoxy-18-hydroxy-16,;6,7-epoxy-10-phenyl-5,6,16,18-tetramethyl-21,23-dioxa-[13]cytochalas-13,19-die;CYTOCHALASIN 3;CYTOCHALASIN E;CYTOCHALASIN E, ASPERGILLUS CLAVATUS
• CAS NO: 36011-19-5
• Molecular Formula: C₂₈H₃₃NO₇
• Molecular Weight: 495.56
• EINECS: 252-835-7
• Product Categories: Actin Inhibitors and ProbesCell Signaling and Neuroscience;Cell Signaling and Neuroscience;Cytoskeleton and Extracellular Matrix;Mold;Toxins and Venoms;antibiotic
• Mol File: 36011-19-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 206 °C
• Boiling Point: 587.59°C (rough estimate)
• Flash Point: 380.205 °C
• Appearance: White powder
• Density: 1.2415 (rough estimate)
• Vapor Pressure: 7.28E-21mmHg at 25°C
• Refractive Index: 1.6290 (estimate)
• Storage Temp.: −20°C
• BRN: 1096975
• CAS DataBase Reference: CYTOCHALASIN E(CAS DataBase Reference)
• NIST Chemistry Reference: CYTOCHALASIN E(36011-19-5)
• EPA Substance Registry System: CYTOCHALASIN E(36011-19-5)

Safety Data

• Hazard Codes: T+,T
• Statements: 26/27/28-63
• Safety Statements: 28-36/37-45
• RIDADR: UN 1544 6.1/PG 2
• WGK Germany: 3
• RTECS: HA5360000
• F: 10
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 36011-19-5(Hazardous Substances Data)

Usage

Description

Cytochalasin E, a potent mycotoxin derived from a range of fungi, is an epoxide-containing analog of cytochalasin B. It is a white powder that selectively inhibits the growth of endothelial cells, impairing angiogenesis and tumor growth without affecting glucose transport or HIV-1 protease activity. Cytochalasin E is a natural product found in Arthrinium sacchari and has diverse applications in various fields due to its unique properties.

Uses

Used in Pharmaceutical Applications:
Cytochalasin E is used as an angiogenesis inhibitor for its ability to impair angiogenesis and tumor growth. It acts as a microfilament inhibitor, enhancing the low-affinity Fc epsilon receptor (CD23) expression.
Used in Research and Development:
Cytochalasin E is used as a toxin to study its effects on avocado plants, providing insights into plant-fungus interactions and potential applications in agriculture.
Used in Cellular and Molecular Biology:
Cytochalasin E is used as a component of the incubating medium in feline junctional adhesion molecule 1 (fJAM-1) expression assay, aiding in the study of cellular adhesion and related processes.
Used in Cell Biology Studies:
Cytochalasin E is used as an inhibitor of actin polymerization to study its effects on mitochondria uptake by mice endothelial cells, contributing to the understanding of cellular processes and mechanisms.
Used in Antimicrobial Applications:
Cytochalasin E is used as an antimicrobial and antibacterial agent due to its fungal metabolite properties, offering potential applications in the development of new antimicrobial treatments.

Biochem/physiol Actions

Cytochalasin E is an epoxide that exhibits anti-proliferative activity in endothelial cells in vitro. It also participates in inhibiting tumor growth and angiogenesis in vivo. Cytochalasin E also possesses antimicrobial and antiviral properties.

InChI:InChI=1/C28H33NO7/c1-16-9-8-12-19-23-27(4,35-23)17(2)21-20(15-18-10-6-5-7-11-18)29-24(31)28(19,21)36-25(32)34-14-13-26(3,33)22(16)30/h5-8,10-14,16-17,19-21,23,33H,9,15H2,1-4H3,(H,29,31)/b12-8+,14-13+

Downstream Products

• 50650-31-2 (3aS)-3c-benzyl-5c,6c-epoxy-7a-hydroxy-7t-hydroxymethyl-4t,5t-dimethyl-(3ar,7ac)-octahydro-isoindol-1-one 
• 81657-75-2 Carbonic acid (1aR,2S,3S,5aS,6S,6aS)-3-benzyl-6-((E)-(4S,6S)-6-hydroxy-4,6-dimethyl-5,8-dioxo-oct-1-enyl)-1a,2-dimethyl-5-oxo-octahydro-1-oxa-4-aza-cyclopropa[f]inden-5a-yl ester methyl ester 
• 81657-78-5 7,18-dihydroxy-16,18-dimethyl-10-phenyl-21,23-dioxo<13>-cytochalasa-6(12),13(E),19(E)triene-1,17,22-trione 
• 81657-79-6 cytochalasin K 
• 81657-76-3 C₂₈H₃₅NO₇ 
• 81657-77-4 Carbonic acid (1aR,2S,3S,5aS,6S,6aS)-3-benzyl-1a,2-dimethyl-5-oxo-6-((E)-(4S,5S,6S)-5,6,8-trihydroxy-4,6-dimethyl-oct-1-enyl)-octahydro-1-oxa-4-aza-cyclopropa[f]inden-5a-yl ester ethyl ester 
• 81657-77-4 Carbonic acid (1aR,2S,3S,5aS,6S,6aS)-3-benzyl-1a,2-dimethyl-5-oxo-6-((E)-(4S,5R,6S)-5,6,8-trihydroxy-4,6-dimethyl-oct-1-enyl)-octahydro-1-oxa-4-aza-cyclopropa[f]inden-5a-yl ester ethyl ester 
• 81657-74-1 19,20-dihydrocytochalasin E 
• 81657-78-5 (5E,11E)-(1S,7R,9S,13S,14S,16S,17S,18S)-18-Benzyl-7,14-dihydroxy-7,9,16-trimethyl-15-methylene-2,4-dioxa-19-aza-tricyclo[11.7.0.0^1,17]icosa-5,11-diene-3,8,20-trione 
• 81672-05-1 7-O-acetylcytochalasin K 

Relevant articles and documents

A carbonate-forming Baeyer-Villiger monooxygenase

Despite the remarkable versatility displayed by flavin-dependent monooxygenases (FMOs) in natural product biosynthesis, one notably missing activity is the oxidative generation of carbonate functional groups. We describe a multifunctional Baeyer-Villiger monooxygenase, CcsB, which catalyzes the formation of an in-line carbonate in the macrocyclic portion of cytochalasin E. This study expands the repertoire of activities of FMOs and provides a possible synthetic strategy for transformation of ketones into carbonates.