1,9-Dideoxyforskolin

Base Information

• Chemical Name: 1,9-Dideoxyforskolin
• CAS No.: 64657-18-7
• Molecular Formula: C22H34 O5
• Molecular Weight: 378.5024
• European Community (EC) Number: 805-078-7
• UNII: OAW710HWIX
• DSSTox Substance ID: DTXSID5040384
• Wikidata: Q27070796
• Metabolomics Workbench ID: 28502
• ChEMBL ID: CHEMBL519570
• Mol file: 64657-18-7.mol

Synonyms:1,9-dideoxyforskolin

Chemical Property of 1,9-Dideoxyforskolin

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 3.43E-10mmHg at 25°C
• Melting Point: 149-150℃
• Boiling Point: 455 °C at 760 mmHg
• Flash Point: 146.9 °C
• PSA: 72.83000
• Density: 1.12 g/cm3
• LogP: 3.43420
• Storage Temp.: −20°C
• Solubility.: methanol: 28 mg/mL
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 378.24062418
• Heavy Atom Count: 27
• Complexity: 670

Purity/Quality:

98% ^*data from raw suppliers

1,9-Dideoxyforskolin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OC1C(C2C(CCCC2(C3C1(OC(CC3=O)(C)C=C)C)C)(C)C)O
• Isomeric SMILES: CC(=O)O[C@H]1[C@H]([C@@H]2[C@](CCCC2(C)C)([C@@H]3[C@@]1(O[C@@](CC3=O)(C)C=C)C)C)O
• Description: Forskolin is a naturally-occurring diterpene that activates adenylyl cyclase through its catalytic subunit and is commonly used to raise levels of cAMP in a wide variety of intact cells and tissue preparations. 1,9-dideoxy Forskolin is an analog of forskolin that interacts with, but does not activate, adenylyl cyclase.
• Uses: 1,9-Dideoxyforkskolin does not activate adenylyl cyclase and is an inactive analog of Forskolin (F701800), a diterpene isolated from Coleus forskohlii, possessing vasodilating and cardiostimulatory properties. Forskolin resensitizes cell receptors by activating the enzyme adenylyl cyclase and increasing the intracellular levels of cAMP.

Technology Process of 1,9-Dideoxyforskolin

There total 13 articles about 1,9-Dideoxyforskolin 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: 86.0%

acetic anhydride (108-24-7) + 7-deacetyl-1,9-dideoxyforskolin (64657-19-8) → 1,9-dideoxyforskolin (64657-18-7)

Guidance literature:

With pyridine; dmap; at 0 ℃; for 1h;

DOI:10.1016/S0040-4039(03)00236-3

Reference yield:

(1S,7S,9S,3R,5R,8R,14R)-14-acetyloxy-8,9-dihydroxy-1,5,7,11,11-pentamethyl-6-oxa-5-vinyltricyclo[8.4.0.02,7]tetradec-3-yl acetate (157201-96-2) → 1,9-dideoxyforskolin (64657-18-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / p-toluenesulfonic acid / 24 h / 50 °C

2: 96 percent / lithium aluminumhydride / diethyl ether / 2.5 h / 20 °C

3: 89 percent / pyridinium chlorochromate; sodium acetate / CH₂Cl₂ / 3 h / 20 °C

4: 82 percent / (dimethylamino)pyridine / diethyl ether / 2.5 h / 50 °C

5: 86 percent / tributyltinhydride; azobisisobutyronitrile / toluene / 0.25 h / 100 °C

6: 100 percent / perchloric acid / tetrahydrofuran / 109 h / 20 °C

7: 86 percent / (dimethylamino)pyridine / pyridine / 1 h / 0 °C

With dmap; lithium aluminium tetrahydride; perchloric acid; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium acetate; toluene-4-sulfonic acid; pyridinium chlorochromate; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; toluene;

DOI:10.1021/jo060477e

Reference yield:

ptychantin A → 1,9-dideoxyforskolin (64657-18-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / potassium hydroxide / methanol / 13.5 h / 20 °C

2: 93 percent / p-toluenesulfonic acid / 24 h / 50 °C

3: 96 percent / lithium aluminumhydride / diethyl ether / 2.5 h / 20 °C

4: 89 percent / pyridinium chlorochromate; sodium acetate / CH₂Cl₂ / 3 h / 20 °C

5: 82 percent / (dimethylamino)pyridine / diethyl ether / 2.5 h / 50 °C

6: 86 percent / tributyltinhydride; azobisisobutyronitrile / toluene / 0.25 h / 100 °C

7: 100 percent / perchloric acid / tetrahydrofuran / 109 h / 20 °C

8: 86 percent / (dimethylamino)pyridine / pyridine / 1 h / 0 °C

With dmap; potassium hydroxide; lithium aluminium tetrahydride; perchloric acid; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium acetate; toluene-4-sulfonic acid; pyridinium chlorochromate; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1021/jo060477e

upstream raw materials:

acetic anhydride

7-deacetyl-1,9-dideoxyforskolin

(2S,7S,13S,6R,9R)-4,4,7,9,13,17,17-heptamethyl-3,5,8-trioxa-9-vinyltetracyclo[11.4.0.0^2,60^7,12]heptadecan-11-one

(1S,7S,9S,3R,5R,8R,14R)-14-acetyloxy-8,9-dihydroxy-1,5,7,11,11-pentamethyl-6-oxa-5-vinyltricyclo[8.4.0.0^2,7]tetradec-3-yl acetate

Downstream raw materials:

1-deoxyforskolin

(14<*>,12E)-7β-acetoxy-8,14-dihydroxy-15-phenylselanyl-6β-trimethylsilanyloxy-labd-12-en-11-one

Refernces

• 1、 Hagiwara, Hisahiro,Takeuchi, Fumihide,Hoshi, Takashi,Suzuki, Toshio,Hashimoto, Toshihiro,Asakawa, Yoshinori. "First synthesis of 1,9-dideoxyforskolin from ptychantin A". . p. 2305 - 2306. Retrieved 2007/10/03.