10H-Cycloundec(d)oxireno(f)isoindol-10-one, 9-(acetyloxy)-3,4,5,6,9,11,12,12a,13,13a,14a,14b-dodecahydro-6-hydroxy-4,6,13,13a-tetramethyl-12-(phenylmethyl)-, (1E,4S,6R,7E,9R,9aR,12S,12aR,13S,13aR,14aS,14bR)-

Base Information

• Chemical Name: 10H-Cycloundec(d)oxireno(f)isoindol-10-one, 9-(acetyloxy)-3,4,5,6,9,11,12,12a,13,13a,14a,14b-dodecahydro-6-hydroxy-4,6,13,13a-tetramethyl-12-(phenylmethyl)-, (1E,4S,6R,7E,9R,9aR,12S,12aR,13S,13aR,14aS,14bR)-
• CAS No.: 80618-96-8
• Deprecated CAS: 96639-05-3
• Molecular Formula: C30H39NO5
• Molecular Weight: 493.6344
• DSSTox Substance ID: DTXSID401338753

Synonyms:Epoxycytochalasin H;80618-96-8;10H-Cycloundec(d)oxireno(f)isoindol-10-one, 9-(acetyloxy)-3,4,5,6,9,11,12,12a,13,13a,14a,14b-dodecahydro-6-hydroxy-4,6,13,13a-tetramethyl-12-(phenylmethyl)-, (1E,4S,6R,7E,9R,9aR,12S,12aR,13S,13aR,14aS,14bR)-;21-Acetoxy-6,7-epoxy-18-hydroxy-10-phenyl-5,6,16,18-tetramethyl(11)cytochalasa-13,19-dien-1-one;DTXSID401338753

Chemical Property of 10H-Cycloundec(d)oxireno(f)isoindol-10-one, 9-(acetyloxy)-3,4,5,6,9,11,12,12a,13,13a,14a,14b-dodecahydro-6-hydroxy-4,6,13,13a-tetramethyl-12-(phenylmethyl)-, (1E,4S,6R,7E,9R,9aR,12S,12aR,13S,13aR,14aS,14bR)-

Chemical Property:

• Vapor Pressure: 1.13E-17mmHg at 25°C
• Boiling Point: 647.9°Cat760mmHg
• Flash Point: 345.7°C
• Density: 1.2g/cm³
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 493.28282334
• Heavy Atom Count: 36
• Complexity: 940

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC=CC2C3C(O3)(C(C4C2(C(C=CC(C1)(C)O)OC(=O)C)C(=O)NC4CC5=CC=CC=C5)C)C
• Isomeric SMILES: C[C@H]1C/C=C/[C@H]2[C@H]3[C@](O3)([C@H]([C@@H]4C2([C@@H](/C=C/[C@](C1)(C)O)OC(=O)C)C(=O)N[C@H]4CC5=CC=CC=C5)C)C

Technology Process of 10H-Cycloundec(d)oxireno(f)isoindol-10-one, 9-(acetyloxy)-3,4,5,6,9,11,12,12a,13,13a,14a,14b-dodecahydro-6-hydroxy-4,6,13,13a-tetramethyl-12-(phenylmethyl)-, (1E,4S,6R,7E,9R,9aR,12S,12aR,13S,13aR,14aS,14bR)-

There total 1 articles about 10H-Cycloundec(d)oxireno(f)isoindol-10-one, 9-(acetyloxy)-3,4,5,6,9,11,12,12a,13,13a,14a,14b-dodecahydro-6-hydroxy-4,6,13,13a-tetramethyl-12-(phenylmethyl)-, (1E,4S,6R,7E,9R,9aR,12S,12aR,13S,13aR,14aS,14bR)- 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:

Epoxycytochalasin J (121981-24-6,80618-95-7) + acetic anhydride (108-24-7) → Epoxycytochalasin H (80618-96-8,96639-05-3)

Guidance literature:

In pyridine; for 3h; Yield given; Ambient temperature;

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

Reference yield: 30.0%

Epoxycytochalasin H (80618-96-8,96639-05-3) → cytochalasin H (53760-19-3) + Cytochalasin Npho (108050-28-8) + Cytochalasin Ppho (108050-27-7)

Guidance literature:

With trifluoroacetic acid; In acetonitrile;

DOI:10.1248/cpb.35.902

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 J

acetic anhydride

Downstream raw materials:

cytochalasin H

Cytochalasin N_pho

Cytochalasin P_pho

Epoxycytochalasin J

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.

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