Jolkinolide A

Base Information

• Chemical Name: Jolkinolide A
• CAS No.: 37905-07-0
• Molecular Formula: C20H26O3
• Molecular Weight: 314.4186
• NSC Number: 700085
• DSSTox Substance ID: DTXSID10958922
• Nikkaji Number: J18.287G
• Wikidata: Q27138166
• Metabolomics Workbench ID: 125960
• ChEMBL ID: CHEMBL1982058
• Mol file: 37905-07-0.mol

Synonyms:jolkinolide A

Chemical Property of Jolkinolide A

Chemical Property:

• Vapor Pressure: 2.35E-09mmHg at 25°C
• Boiling Point: 479.5°Cat760mmHg
• Flash Point: 206.7°C
• PSA: 38.83000
• Density: 1.19g/cm³
• LogP: 4.13740
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 314.18819469
• Heavy Atom Count: 23
• Complexity: 685

Purity/Quality:

Analysis control,HPLC≥95% ^*data from raw suppliers

JolkinolideA 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C2C3C4(O3)CCC5C(CCCC5(C4C=C2OC1=O)C)(C)C
• Isomeric SMILES: CC1=C2[C@@H]3[C@]4(O3)CC[C@H]5[C@]([C@@H]4C=C2OC1=O)(CCCC5(C)C)C
• Uses: Jolkinolide A can be used as a bone marrow mesenchymal stem cell osteogenic differentiation accelerator. It can be developed using matrix solid-phase dispersion coupled with high-performance liquid chromatography.

Technology Process of Jolkinolide A

There total 4 articles about Jolkinolide A 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: 84.0%

2-(Diethoxy-phosphoryl)-propionic acid (3aS,4aS,6aR,10aR,10bS)-7,7,10a-trimethyl-3-oxo-3,5,6,6a,7,8,9,10,10a,10b-decahydro-3aH-4-oxa-cyclopropa[j]phenanthren-2-yl ester → jolkinolide A (37905-07-0,86746-85-2,97906-88-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 3h;

DOI:10.1055/s-0034-1378317

Reference yield:

ent-8β,14β-epoxy-13-podocarpanone → jolkinolide A (37905-07-0,86746-85-2,97906-88-2)

Guidance literature:

Multi-step reaction with 3 steps

1: oxygen; potassium tert-butylate / tert-butyl alcohol / 0.67 h / 40 °C

2: dicyclohexyl-carbodiimide; dmap / dichloromethane / 10 h / 20 °C

3: sodium hydride / tetrahydrofuran / 3 h / 0 - 20 °C

With dmap; potassium tert-butylate; oxygen; sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; tert-butyl alcohol; 2: |Wittig-Horner Reaction;

DOI:10.1055/s-0034-1378317

Reference yield:

2-(Diethoxy-phosphoryl)-propionic acid (2R,3aS,4aS,6aR,10aR,10bS)-7,7,10a-trimethyl-3-oxo-dodecahydro-4-oxa-cyclopropa[j]phenanthren-2-yl ester → jolkinolide A (37905-07-0,86746-85-2,97906-88-2)

Guidance literature:

With sodium hydride; In 1,2-dimethoxyethane; for 0.5h; Yield given; Ambient temperature;

DOI:10.1016/0040-4020(89)80132-2

Downstream raw materials:

jolkinolide B

jolkinolide B

Refernces

• 1、 -. "Natural crag root of beijing euphorbia lactone Jolkinolide A and B synthetic method". Page/Page column 13; 15. . Retrieved 2017/08/23.
• 2、 Katsumura, Shigeo,Kimura, Akihiko,Isoe, Sachihiko. "TOTAL SYNTHESIS OF (+/-)-JOLKINOLIDE A, B, AND E UTILIZING A NEW MILD ESTERIFICATION FOLLOWED BY INTRAMOLECULAR WITTIG-HORNER REACTION". . p. 1337 - 1346. Retrieved 2007/10/02.