[(3E,9Z)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylidene-6,18-dioxo-17-azatricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl] acetate

Base Information Edit

Chemical Name:[(3E,9Z)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylidene-6,18-dioxo-17-azatricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl] acetate
CAS No.:22144-77-0
Molecular Formula:C30H37 N O6
Molecular Weight:507.627
Hs Code.:29337900
UN Number:3172
Metabolomics Workbench ID:143732
Wikipedia:Cytochalasin_D
Mol file:22144-77-0.mol

[(3E,9Z)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylidene-6,18-dioxo-17-azatricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl] acetate

Synonyms:Cytochalasin D

Suppliers and Price of [(3E,9Z)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylidene-6,18-dioxo-17-azatricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl] acetate

Supply Marketing:Edit

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Usbiological
Cytochalasin D
1mg
$ 403.00

Usbiological
Cytochalasin D
100mg
$ 2867.00

TRC
Cytochalasin D
5mg
$ 690.00

Tocris
Cytochalasin D ≥95%(HPLC)
1
$ 121.00

Tocris
Cytochalasin D ≥95%(HPLC)
5
$ 492.00

Sigma-Aldrich
Cytochalasin D from Zygosporium mansonii, ≥98% (TLC and HPLC), powder
5mg
$ 444.00

Sigma-Aldrich
Cytochalasin D from Zygosporium mansonii, ≥98% (TLC and HPLC), powder
10mg
$ 873.00

Sigma-Aldrich
Cytochalasin D Ready Made Solution, from Zygosporium mansonii, 5?mg/mL in DMSO, 0.2 μm filtered
200 μL
$ 171.00

Sigma-Aldrich
Cytochalasin D Ready Made Solution, from
200ul
$ 169.00

Sigma-Aldrich
Cytochalasin D from Zygosporium mansonii, ≥98% (TLC and HPLC), powder
1mg
$ 137.00

Total 32 raw suppliers

Chemical Property of [(3E,9Z)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylidene-6,18-dioxo-17-azatricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl] acetate Edit

Chemical Property:

Appearance/Colour:powder
Vapor Pressure:2.76E-21mmHg at 25°C
Melting Point:255-260ºC
Refractive Index:1.6310 (estimate)
Boiling Point:712.1°Cat760mmHg
PKA:11.95±0.70(Predicted)
Flash Point:384.5°C
PSA：112.93000
Density:1.23g/cm³
LogP:3.24590
Storage Temp.:−20°C
Solubility.:DMSO: soluble
XLogP3:2.7
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:507.26208790
Heavy Atom Count:37
Complexity:996
Transport DOT Label:Poison

Purity/Quality:

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

Cytochalasin D ^*data from reagent suppliers

Safty Information:

Pictogram(s): T
Hazard Codes:T
Statements: 25-63
Safety Statements: 36/37-45

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC1CC=CC2C(C(=C)C(C3C2(C(C=CC(C1=O)(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=O)(C)O)OC(=O)C)C(=O)NC3CC4=CC=CC=C4)C)O
Description Cytochalasin D (22144-77-0) is a potent inhibitor of actin polymerization which also causes the disruption of actin filaments. More potent that cytochalasin B (10-fold) and does not inhibit monosaccharide transport across cell membranes. Disruption of actin microfilaments leads to activation of p53. Cell permeable
Uses Cytochalasin D acts as an anti-hypertensive drug acting on human intestinal epithelial caco-2 cells. Also has activity in HMG-CoA reductase inhibitors used in the lowering of cholesterol. Actin inhib itor, actin polymerization inhibitor affecting cell movement, growth, phagocytosis and even secretion. Cytochalasin D is the most studied of the cytochalasins. Like most of the members of this mycotoxin class, cytochalasin D exhibits potent inhibition of actin filament function leading to cell death by apoptosis. This led to early investigation of the metabolite as an antitumour agent. Cytochalasin D has become one of the standard cellular probes for investigating the role of actin in cell biology. A cell cycle arresting compound used in actin polymerization studies and cytological research

Technology Process of [(3E,9Z)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylidene-6,18-dioxo-17-azatricyclo[9.7.0.01,15]octadeca-3,9-dien-2-yl] acetate

There total 27 articles about [(3E,9Z)-16-benzyl-5,12-dihydroxy-5,7,14-trimethyl-13-methylidene-6,18-dioxo-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%

: Acetic acid (3E,9E)-(1R,2R,5R,7S,11R,12S,14S,15R,16S)-16-benzyl-12-(ethoxy-trimethylsilanyl-methoxy)-5-hydroxy-5,7,14-trimethyl-13-methylene-6,18-dioxo-17-aza-tricyclo[9.7.0.0^1,15]octadeca-3,9-dien-2-yl ester

: 22144-77-0
cytochalasin D

Guidance literature:: With hydrogen fluoride; In water; acetonitrile;
DOI:10.1039/c39900000464

Reference yield: 69.0%

: 129056-46-8
(7S,13E,16S,18R,19E,21R)-21-Acetoxy-18-hydroxy-16,18-dimethyl-7-(2-trimethylsilylethoxymethoxy)-10-phenyl[11]cytochalasa-6⁽¹²⁾,13,19-triene-1,17-dione

: 22144-77-0
cytochalasin D

Guidance literature:: With hydrogen fluoride; water; In acetonitrile; at 20 ℃; for 6.5h;
DOI:10.1039/a906412e

Reference yield:

: 94063-58-8
(5R)-1-benzoyl-5-benzylpyrrolidin-2-one

: 22144-77-0
cytochalasin D

Guidance literature:: Multi-step reaction with 19 steps

1.1: LiN(SiMe₃)2 / tetrahydrofuran; hexane / 1 h / -70 °C

1.2: 92 percent / tetrahydrofuran / 4 h / -70 - 20 °C

2.1: LiN(SiMe₃)2 / tetrahydrofuran; hexane / 1 h / -70 °C

2.2: 100 percent / tetrahydrofuran; hexane / 2 h / -70 °C

3.1: H₂O₂; MCPBA / H₂O; CHCl₃ / 0.33 h / -50 - 0 °C

4.1: benzene / 8 h / Heating

5.1: 53 percent / OsO₄ / pyridine / 1 h / -15 °C

6.1: 89 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

7.1: 85 percent / NEt₃; SOCl₂ / CH₂Cl₂ / 0.5 h / -20 °C

8.1: 75 percent / OsO₄ / pyridine / 0.5 h / -25 °C

9.1: 99 percent / p-TsOH / CHCl₃ / 5 h / 20 °C

10.1: LiN(SiMe₃)2 / tetrahydrofuran / 0.5 h / -35 °C

10.2: 70 percent / tetrahydrofuran / 1.5 h / -35 °C

11.1: 97 percent / NaOH; H₂O / methanol / 3 h / 20 °C

12.1: 65 percent / H₂O₂; pyridine / CH₂Cl₂; H₂O / 3 h / 20 °C

13.1: 93 percent / NaBH₄; CeCl₃*7H₂O / methanol / 10 °C

14.1: 81 percent / NEt₃; DMAP / CH₂Cl₂ / 2 h / 20 °C

15.1: 72 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

16.1: 74 percent / diisopropylethylamine / CH₂Cl₂ / 4 h / 20 °C

17.1: 64 percent / HCl; H₂O / tetrahydrofuran / 4 h / 20 °C

18.1: 75 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / -60 - 20 °C

19.1: 69 percent / HF; H₂O / acetonitrile / 6.5 h / 20 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; thionyl chloride; cerium(III) chloride; oxalyl dichloride; hydrogen fluoride; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; chloroform; water; acetonitrile; benzene; 1.1: Metallation / 1.2: Acylation / 2.1: Metallation / 2.2: Phenylselenenylation / 3.1: Oxidation / 4.1: Cycloaddition / 5.1: Oxidation / 6.1: Etherification / 7.1: Dehydration / 8.1: Oxidation / 9.1: Cyclization / 10.1: Metallation / 10.2: Phenylselenenylation / 11.1: Hydrolysis / 12.1: Elimination / 13.1: Reduction / 14.1: Acetylation / 15.1: Desilylation / 16.1: Etherification / 17.1: Hydrolysis / 18.1: Oxidation / 19.1: Hydrolysis;
DOI:10.1039/a906412e