[(3E,9Z)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylidene-18-oxo-17-azatricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl] acetate

Base Information

• Chemical Name: [(3E,9Z)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylidene-18-oxo-17-azatricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl] acetate
• CAS No.: 53760-19-3
• Molecular Formula: C30H39 N O5
• Molecular Weight: 493.643
• European Community (EC) Number: 637-304-3
• Metabolomics Workbench ID: 156645
• Mol file: 53760-19-3.mol

Synonyms:cytochalasin H

Chemical Property of [(3E,9Z)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylidene-18-oxo-17-azatricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl] acetate

Chemical Property:

• Vapor Pressure: 3.17E-19mmHg at 25°C
• Melting Point: 252-258 °C
• Refractive Index: 1.6310 (estimate)
• Boiling Point: 676.5°Cat760mmHg
• PKA: 13.88±0.70(Predicted)
• Flash Point: 362.9°C
• PSA: 95.86000
• Density: 1.19g/cm³
• LogP: 4.06690
• Storage Temp.: 2-8°C
• Solubility.: chloroform: 10 mg/mL, clear, colorless
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 493.28282334
• Heavy Atom Count: 36
• Complexity: 920

Purity/Quality:

98%Min ^*data from raw suppliers

Cytochalasin H ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CC=CC2C(C(=C)C(C3C2(C(C=CC(C1)(C)O)OC(=O)C)C(=O)NC3CC4=CC=CC=C4)C)O
• Isomeric SMILES: CC1C/C=C\C2C(C(=C)C(C3C2(C(/C=C/C(C1)(C)O)OC(=O)C)C(=O)NC3CC4=CC=CC=C4)C)O
• Uses: Cytochalasin H is one of a family of potent mycotoxins produced by a range of fungi. All members of the class exhibit profound effects on cytoskeletal proteins, resulting in pronounced morphogenic changes in animals and plants. In vitro, cytochalasin H exhibits antibacterial, antifungal, nematocidal and antitumour activity.

Technology Process of [(3E,9Z)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylidene-18-oxo-17-azatricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl] acetate

There total 42 articles about [(3E,9Z)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylidene-18-oxo-17-azatricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl] acetate 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: 70.0%

(7S,16S,18R,21R)-21-acetoxy-7-hydroxy-16,18-dimethyl-10-phenyl-18-(2-trimethylsilylethoxymethoxy)<11>cytochalasa-6(12),13t,19t-trien-1-one (104702-08-1) → cytochalasin H (53760-19-3)

Guidance literature:

With hydrogen fluoride; In acetonitrile;

DOI:10.1039/c39860000727

Reference yield: 60.0%

Acetic acid (3E,9E)-(1R,2R,5R,7S,11R,12S,14S,15R,16S)-16-benzyl-5,7,14-trimethyl-13-methylene-18-oxo-5,12-bis-(2-trimethylsilanyl-ethoxymethoxy)-17-aza-tricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl ester (104842-18-4) → cytochalasin H (53760-19-3)

Guidance literature:

With hydrogen fluoride; In acetonitrile;

DOI:10.1039/c39860000727

Reference yield:

Epoxycytochalasin H (80618-96-8,96639-05-3) → cytochalasin H (53760-19-3)

Guidance literature:

With aluminum isopropoxide; In toluene; at 150 ℃; for 8h; Yield given;

DOI:10.1016/S0040-4020(01)83434-7

upstream raw materials:

Epoxycytochalasin H

(7S,16S,18R,21R)-21-acetoxy-7-hydroxy-16,18-dimethyl-10-phenyl-18-(2-trimethylsilylethoxymethoxy)<11>cytochalasa-6(12),13^t,19^t-trien-1-one

Acetic acid (3E,9E)-(1R,2R,5R,7S,11R,12S,14S,15R,16S)-16-benzyl-5,7,14-trimethyl-13-methylene-18-oxo-5,12-bis-(2-trimethylsilanyl-ethoxymethoxy)-17-aza-tricyclo[9.7.0.0^1,15]octadeca-3,9-dien-2-yl ester

(16S,18R)-16,18-dimethyl-10-phenyl-18-(2-trimethylsilylethoxymethoxy)<11>cytochalasa-6(7),13^t,19^t-triene-1,21-dione

Downstream raw materials:

deacetylcytochalasin H

Refernces

The effects of new cytochalasins from Phomopsis sp. and the derivatives on cellular structure and actin polymerization

10.1248/cpb.38.971

This study investigated the effects of ten 10-phenyl-[11]cytochalasins produced by Phomopsis sp., including novel compounds with 5,7- or 6,7-diol structures and their derivatives, such as epoxycytochalasin H, cytochalasin H, cytochalasin J, cytochalasin N, cytochalasin O, and cytochalasin P, on cell structure and actin polymerization. Their effects on cell morphology, actin distribution in C3H-2K cells, lymphocyte capping, and actin polymerization were also investigated. The results confirmed previously reported structure-activity relationships, indicating that the perhydroisoindol-1-one core is essential for the effects of cytochalasins. The novel diol-type compounds showed little or no activity. The effects of five derivatives were also investigated to elucidate the influence of the physical properties of the compounds, such as lipophilicity, on their effectiveness. These findings provide insights into the structure-activity relationships of cytochalasins and their potential cellular and actin-related effects.