CID 127632

Base Information

• Chemical Name: CID 127632
• CAS No.: 64657-20-1
• Molecular Formula: C20H32 O6
• Molecular Weight: 368.47
• European Community (EC) Number: 613-647-4
• DSSTox Substance ID: DTXSID90983272
• Wikidata: Q82970192
• Mol file: 64657-20-1.mol

Synonyms:7-desacetylforskolin

Chemical Property of CID 127632

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 177 °C
• Boiling Point: 512.083°C at 760 mmHg
• PKA: 11.20±0.70(Predicted)
• Flash Point: 174.807°C
• PSA: 107.22000
• Density: 1.28g/cm³
• LogP: 0.94910
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 368.21988874
• Heavy Atom Count: 26
• Complexity: 646

Purity/Quality:

>97% ^*data from raw suppliers

DesacetylForskolin ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 21
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(CCC(C2(C1C(C(C3(C2(C(=O)CC(O3)(C)C=C)O)C)O)O)C)O)C
• Isomeric SMILES: C[C@@]1(CC(=O)[C@]2([C@@]3([C@@H](CCC([C@H]3[C@H]([C@H]([C@@]2(O1)C)O)O)(C)C)O)C)O)C=C
• Uses: Desacetyl Forskolin is an analogue of Forskolin (F701800). Desacetyl Forskolin was tested for its ability to activate rat brain adenylate cyclase, activate detergent-solubilized rat brain adenylate cyclase, increase cyclic AMP in intact S49 wild-type cells, and inhibit the binding of 3H-forskolin to rat brain membranes.

Technology Process of CID 127632

There total 130 articles about CID 127632 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%

7-deacetyl-6,7-dicarbonateforskolin (81826-82-6) → 7-deacetyl forskolin (64657-20-1)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 1.5h;

DOI:10.1055/s-2008-1042930

Reference yield: 79.0%

C26H40O6 → (+/-)-desacetyl forskolin (64657-20-1,66428-84-0,114298-68-9,119618-16-5,132620-06-5,132620-08-7)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; water; at 23 ℃; for 288h;

DOI:10.1002/anie.201706809

Reference yield: 77.0%

(3aR,3bS,5S,7aR,7bS,8R,11aR,11bR)-7a,8-Dihydroxy-2,2,3b,5,7b,11,11-heptamethyl-5-vinyl-dodecahydro-1,3,4-trioxa-cyclopenta[l]phenanthren-7-one (114273-88-0,115224-64-1) → (+/-)-desacetyl forskolin (64657-20-1,66428-84-0,114298-68-9,119618-16-5,132620-06-5,132620-08-7)

Guidance literature:

In tetrahydrofuran; perchloric acid; at 23 ℃; for 60h;

DOI:10.1021/ja00219a058

upstream raw materials:

forskolin

(6S,11S,16S,1R,2R,12R,13R)-14-methoxy-1,4,4,8,8,12,16-heptamethyl-3,5,17-trioxa-16-vinyltetracyclo[11.4.0.0.^2,60^7,12]heptadec-14-en-11,13-diol

(1S,6S,12S,16S,2R)-14-hydroxy-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

(2S,7S,13S,14S,6R,9R)-14-hydroxy-4,4,7,9,13,17,17-heptamethyl-3,5,8-trioxa-9-vinyltetracyclo[11.4.0.0^2,60^7,12]heptadec-11-one

Downstream raw materials:

7β-anilinocarbonyloxy-8,13-epoxy-1α,6β,9α-trihydroxylabd-14-en-11-one

C₂₂H₃₄O₇

forskolin

7β-(tert-butyldimethylsiloxy)-8,13-epoxy-6β,9α-dihydroxy-11-oxolabd-14-en-1-α-yl diphenylphosphate

Refernces

• 1、 Ziegler, Frederick E.,Jaynes, Burton H.. "RECONSTITUTION OF FORSKOLIN FROM A RING C DIHYDROPYRAN-4-ONE DEGRADATION PRODUCT THEREOF". . p. 2339 - 2342. Retrieved 1987.
• 2、 Thomas, William P.,Schatz, Devon J.,George, David T.,Pronin, Sergey V.. "A Radical-Polar Crossover Annulation to Access Terpenoid Motifs". supporting information. p. 12246 - 12250. Retrieved 2019/08/27.
• 3、 Mohankumar, Ramasamy,Ilango, Kaliappan,Santhanakrishnan, Vichangal Pridiuldi,Radhakrishnan, Viswanathan,Narasimhan, Srinivasan. "Ethylenediamine: An effective reagent for deacetylation of natural products". experimental part. p. 851 - 858. Retrieved 2010/12/25.