24-Oxa(14)cytochalasa-6(12),13,21-triene-1,23-dione, 7,20-dihydroxy-16-methyl-10-phenyl-, (7S,13E,16R,20R,21E)-

Base Information

• Chemical Name: 24-Oxa(14)cytochalasa-6(12),13,21-triene-1,23-dione, 7,20-dihydroxy-16-methyl-10-phenyl-, (7S,13E,16R,20R,21E)-
• CAS No.: 14930-96-2
• Molecular Formula: C29H37NO5
• Molecular Weight: 479.616
• Hs Code.: 29349990
• European Community (EC) Number: 239-000-2
• Wikipedia: Cytochalasin_B
• Wikidata: Q104167024,Q105106279
• Mol file: 14930-96-2.mol

Synonyms:14930-96-2;HSDB 3479;EINECS 239-000-2;C29-H37-N-O5;BRN 1096207;Neuro_000052;7,20-Dihydroxy-10-phenyl-5,16-dimethyl-24-oxa-(14)cytochalas-6(12),13,21-trien-23-one;(E,E)-(5S,9R,12aS,13S,15S,15aS,16S,18aS)-16-Benzyl-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-2H-oxacyclotetradec(2,3-d)isoindole-2,18(5H)-dione;24-Oxa(14)cytochalasa-6(12),13,21-triene-1,23-dione, 7,20-dihydroxy-16-methyl-10-phenyl-, (7S,13E,16R,20R,21E)-;24-Oxa[14]cytochalasa-6(12),13,21-triene-1,23-dione, 7,20-dihydroxy-16-methyl-10-phenyl-, (7S,13E,16R,20R,21E)-;2H-Oxacyclotetradec(2,3-d)isoindole-2,18(5H)-dione, 16-benzyl-6,7,8,9,10,12a,13,14,15,15a,16,17-dodecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-, (E,E)-(5S,9R,12aS,13S,15S,15aS,16S,18aS)-;7(S),20(R)-dihydroxy-16(R)-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13(E),21(E)-triene-1,23-dione;SMP1_000088;NCI60_000181;FT-0624329

Chemical Property of 24-Oxa(14)cytochalasa-6(12),13,21-triene-1,23-dione, 7,20-dihydroxy-16-methyl-10-phenyl-, (7S,13E,16R,20R,21E)-

Chemical Property:

• Appearance/Colour: white to off-white powder
• Vapor Pressure: 4.98E-23mmHg at 25°C
• Melting Point: 218-223 °C
• Refractive Index: 1.596
• Boiling Point: 740.559 °C at 760 mmHg
• PKA: 13.60±0.70(Predicted)
• Flash Point: 401.676 °C
• PSA: 95.86000
• Density: 1.209 g/cm³
• LogP: 3.82090
• Storage Temp.: −20°C
• Solubility.: ethanol: 20 mg/mL
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 479.26717328
• Heavy Atom Count: 35
• Complexity: 859

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cytochalasin B ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+, T
• Hazard Codes: T+,T
• Statements: 26/27/28-63-23/24/25
• Safety Statements: 28-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Mycotoxins
• Canonical SMILES: CC1CCCC(C=CC(=O)OC23C(C=CC1)C(C(=C)C(C2C(NC3=O)CC4=CC=CC=C4)C)O)O
• Description: Cytochalasin B (14930-96-2) is a cell permeable fungal toxin which binds to the barbed end of actin, inhibiting its polymerization.1 Inhibits cell division, migration and glucose transport.2 Causes cell cycle arrest at G2/M and induces apoptosis in HCT-116 colorectal carcinoma cells.3? Cytochalasin B-induced membrane vesicles (CIMVs) retain cell surface receptors of the parent cells and retain fusion specificity with target cells.4 CIMVs are a promising new vector system for drug and biomolecule delivery due to their natural origin and participation in intercellular communication.5
• Uses: 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. A cell-permeable fungal toxin used in actin polymerization studies and cytological As tools in cytological research and in characterization of polymerization properties of actin, q.v.

Technology Process of 24-Oxa(14)cytochalasa-6(12),13,21-triene-1,23-dione, 7,20-dihydroxy-16-methyl-10-phenyl-, (7S,13E,16R,20R,21E)-

There total 9 articles about 24-Oxa(14)cytochalasa-6(12),13,21-triene-1,23-dione, 7,20-dihydroxy-16-methyl-10-phenyl-, (7S,13E,16R,20R,21E)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(16R,20R)-7β,20-diacetoxy-9-hydroxy-16-methyl-1-oxo-10-phenyl-9,23-seco-[13]cytochalasa-6(12),13t,21t-triene-23-thioic acid S-phenyl ester (64760-39-0) → cytochalasin B (14930-96-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Na₂HPO₄, CF₃CO₂Ag / benzene

2: (alkaline hydrolysis)

With disodium hydrogenphosphate; silver trifluoroacetate; In benzene;

DOI:10.1021/ja00462a049

Reference yield:

7,20-O,O'-di-acetyl-cytochalasin B (14903-09-4) → cytochalasin B (14930-96-2)

Guidance literature:

(alkaline hydrolysis);

DOI:10.1021/ja00462a049

Reference yield:

→ cyctochalasin B (14930-96-2)

Guidance literature:

Cytochalasin A, NaBH4;

upstream raw materials:

7,20-O,O'-di-acetyl-cytochalasin B

(16R,20R)-7β,20-diacetoxy-9-hydroxy-16-methyl-1-oxo-10-phenyl-9,23-seco-[13]cytochalasa-6(12),13t,21t-triene-23-thioic acid S-phenyl ester

C₃₇H₅₃NO₆Si

(4E,12E)-(1R,6R,10S,14S,17S,18S,19S)-19-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10,16,17-trimethyl-2-oxa-20-aza-tricyclo[12.7.0.0^1,18]henicosa-4,12,15-triene-3,21-dione

Downstream raw materials:

(16R,20R,21Ξ)-7β,9,20-trihydroxy-21-methoxy-16-methyl-1-oxo-10-phenyl-9,23-seco-[13]cytochalasa-6(12),13t-dien-23-oic acid 20-lactone

cytochalasin A

7β,20β-dihydroxy-16α-methyl-10-phenyl-(6ξH)-24-oxa-[14]cytochalasane-1,23-dione

(16R,20Ξ)-7β,9,20-trihydroxy-16-methyl-1-oxo-10-phenyl-(4α)-9,23-seco-[13]cytochalasa-6(12),13t-dien-23-oic acid 20-lactone

Refernces

• 1、 Masamune,Hayase,Schilling,Chan,Bates. "Activation of thiol esters. Partial synthesis of cytochalasins A and B.". . p. 6756 - 6758. Retrieved 2007/10/05.