Withanolide E

Base Information

Chemical Name:Withanolide E
CAS No.:38254-15-8
Molecular Formula:C28H38O7
Molecular Weight:486.5971
Hs Code.:
NSC Number:179834
DSSTox Substance ID:DTXSID10959191
Nikkaji Number:J19.199J
Wikidata:Q82939831
ChEMBL ID:CHEMBL1097107
Mol file:38254-15-8.mol

Synonyms:WITHANOLIDE E;38254-15-8;NSC179834;SCHEMBL2231888;CHEMBL1097107;DTXSID10959191;BDBM50437341;NSC-179834;14,17,20-Trihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione;Ergosta-2, 5,6-epoxy-14,17,20,22-tetrahydroxy-1-oxo-, .gamma.-lactone;Ergosta-2, 5,6-epoxy-14,17,20,22-tetrahydroxy-1-oxo-, .gamma.-lactone, (5.beta.,6.beta.,17.alpha.,22R)-

Suppliers and Price of Withanolide E

Supply Marketing:

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

American Custom Chemicals Corporation
WITHANOLIDE E 95.00%
5MG
$ 496.68

Total 14 raw suppliers

Chemical Property of Withanolide E

Chemical Property:

Vapor Pressure:1.31E-21mmHg at 25°C
Boiling Point:683.1°Cat760mmHg
Flash Point:226.5°C
PSA：116.59000
Density:1.34g/cm³
LogP:2.75440
XLogP3:1.7
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:2
Exact Mass:486.26175355
Heavy Atom Count:35
Complexity:1090

Purity/Quality:

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

WITHANOLIDE E 95.00% ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC1=C(C(=O)OC(C1)C(C)(C2(CCC3(C2(CCC4C3CC5C6(C4(C(=O)C=CC6)C)O5)C)O)O)O)C
Isomeric SMILES:CC1=C(C(=O)O[C@H](C1)[C@@](C)([C@@]2(CC[C@@]3([C@@]2(CC[C@H]4[C@H]3C[C@@H]5[C@]6([C@@]4(C(=O)C=CC6)C)O5)C)O)O)O)C

Technology Process of Withanolide E

There total 22 articles about Withanolide E 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: 50.0%

: 108030-78-0
withanolide C

: 38254-15-8
(+)-withanolide E

Guidance literature:: With silica gel; In chloroform; at 50 ℃; for 10h;

Reference yield:

: 114028-19-2
1α,3α-diacetoxyandrost-5-ene-17-one

: 38254-15-8
(+)-withanolide E

Guidance literature:: Multi-step reaction with 19 steps

1: (TMS)2NH, Et₃N / 1,2-dichloro-ethane / 0.75 h / -23 °C

2: 1.) Pd(OAc)2, K₂CO₃, 2.) p-toluenesulfonic acid / 1.) CH₃CN, 12 h, 2.) reflux

3: 1.) tetrabutylammonium periodate / 1.) CH₂Cl₂, 2.) 0 deg C, 20 min

4: 1.) H₂, 2.) aq. CuCl₂ / 1.) 5percent Pd-BaSO₄ / 1.) EtOH, 3 h, 2.) THF, 4 h

5: 100 percent / 5percent KOH / methanol / 2 h / Heating

7: tetrahydrofuran

8: i-Pr₂NEt / dioxane / 24 h / 80 °C

9: osmium tetraoxide, pyridine

10: 89 percent / TFAA, DMSO, Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

11: 97 percent / tetrahydrofuran / 1 h / -78 °C

12: 65 percent / i-Pr₂NEt / dioxane / 24 h / 90 °C

13: 1.) O₃, 2.) Me₂S / 1.) MeOH, -100 deg C, 2.) 30 min

14: 1.) LDA / 1.) THF, HMPA, 2.) from -78 deg C to RT, 1.5 h

15: 2 M aq. H₂SO₄ / dioxane / 36 h

16: 72 percent / DMAP, pyridine / 15 h

17: 78 percent / oxidation

18: 1,5-diazabicyclo<4.3.0>non-5-ene / CH₂Cl₂ / 0.67 h

19: MCPBA, NaHCO₃ / CH₂Cl₂ / 18 h

With pyridine; dmap; palladium diacetate; potassium hydroxide; osmium(VIII) oxide; dimethylsulfide; sulfuric acid; DBN; hydrogen; sodium hydrogencarbonate; potassium carbonate; tetrabutylammonium periodite; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic anhydride; copper dichloride; lithium diisopropyl amide; palladium on barium sulfate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1021/ja00003a058

Reference yield:

: Acetic acid (1S,3R,8R,9S,10R,13S,14S)-3-acetoxy-10,13-dimethyl-17-trimethylsilanyloxy-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-1-yl ester

: 38254-15-8
(+)-withanolide E

Guidance literature:: Multi-step reaction with 18 steps

1: 1.) Pd(OAc)2, K₂CO₃, 2.) p-toluenesulfonic acid / 1.) CH₃CN, 12 h, 2.) reflux

2: 1.) tetrabutylammonium periodate / 1.) CH₂Cl₂, 2.) 0 deg C, 20 min

3: 1.) H₂, 2.) aq. CuCl₂ / 1.) 5percent Pd-BaSO₄ / 1.) EtOH, 3 h, 2.) THF, 4 h

4: 100 percent / 5percent KOH / methanol / 2 h / Heating

6: tetrahydrofuran

7: i-Pr₂NEt / dioxane / 24 h / 80 °C

8: osmium tetraoxide, pyridine

9: 89 percent / TFAA, DMSO, Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

10: 97 percent / tetrahydrofuran / 1 h / -78 °C

11: 65 percent / i-Pr₂NEt / dioxane / 24 h / 90 °C

12: 1.) O₃, 2.) Me₂S / 1.) MeOH, -100 deg C, 2.) 30 min

13: 1.) LDA / 1.) THF, HMPA, 2.) from -78 deg C to RT, 1.5 h

14: 2 M aq. H₂SO₄ / dioxane / 36 h

15: 72 percent / DMAP, pyridine / 15 h

16: 78 percent / oxidation

17: 1,5-diazabicyclo<4.3.0>non-5-ene / CH₂Cl₂ / 0.67 h

18: MCPBA, NaHCO₃ / CH₂Cl₂ / 18 h

With pyridine; dmap; palladium diacetate; potassium hydroxide; osmium(VIII) oxide; dimethylsulfide; sulfuric acid; DBN; hydrogen; sodium hydrogencarbonate; potassium carbonate; tetrabutylammonium periodite; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; copper dichloride; lithium diisopropyl amide; palladium on barium sulfate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane;
DOI:10.1021/ja00003a058