64657-20-1

Basic information

• Product Name: 1ALPHA,6BETA,7BETA,9ALPHA-TETRAHYDROXY-8,13-EPOXY-LABD-14-EN-11-ONE
• Synonyms: 1ALPHA,6BETA,7BETA,9ALPHA-TETRAHYDROXY-8,13-EPOXY-LABD-14-EN-11-ONE;FORSKOLIN, 7-DEACETYL-;DEACETYLFORSKOLIN;DEACETYLFORSKOLIN FROM COLEUSFORSKOHLII;1α,6β,7β,9α-tetrahydroxy-8,13-epoxy-labd-14-en-11-one;1H-Naphtho(2,1-b)pyran-1-one, 3-ethenyldodecahydro-5,6,10,10b-tetrahyd roxy-3,4a,7,7,10a-pentamethyl-, (3R-(3alpha,4abeta,5beta,6beta,6aalpha ,10alpha,10abeta,10balpha))-;7-desacetylforskolin;(3R,6aα)-3α-Ethenyldodecahydro-5β,6β,10α,10bα-tetrahydroxy-3,4aβ,7,7,10aβ-pentamethyl-1H-naphtho[2,1-b]pyran-1-one
• CAS NO: 64657-20-1
• Molecular Formula: C₂₀H₃₂O₆
• Molecular Weight: 368.46
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 64657-20-1.mol
• Article Data: 14

Chemical Properties

• Melting Point: 177 °C
• Boiling Point: 512.083°C at 760 mmHg
• Flash Point: 174.807°C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 11.20±0.70(Predicted)
• CAS DataBase Reference: 1ALPHA,6BETA,7BETA,9ALPHA-TETRAHYDROXY-8,13-EPOXY-LABD-14-EN-11-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1ALPHA,6BETA,7BETA,9ALPHA-TETRAHYDROXY-8,13-EPOXY-LABD-14-EN-11-ONE(64657-20-1)
• EPA Substance Registry System: 1ALPHA,6BETA,7BETA,9ALPHA-TETRAHYDROXY-8,13-EPOXY-LABD-14-EN-11-ONE(64657-20-1)

Safety Data

• Hazard Codes: Xn
• Statements: 21
• Safety Statements: 36
• WGK Germany: 3
• Hazardous Substances Data: 64657-20-1(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C20H32O6/c1-7-17(4)10-12(22)20(25)18(5)11(21)8-9-16(2,3)14(18)13(23)15(24)19(20,6)26-17/h7,11,13-15,21,23-25H,1,8-10H2,2-6H3/t11-,13-,14-,15-,17-,18-,19+,20-/m0/s1

Upstream product

• 64657-19-8 7-deacetyl-1,9-dideoxyforskolin 
• 157201-96-2 (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 
• 123218-03-1 rac-5β<<(tert-Butyl)dimethylsilyl>oxy>-4α-ethinyl-1,4,4a,5,6,7,8,8aα-octahydro-4-hydroxy-3,4aα,8,8-tetramethylnaphthalin-1(4H)-on 
• 123218-02-0 rac-8β-<<(tert-Butyl)dimethylsilyl>oxy>-1,4,4aα,5,6,7,8,8a-octahydro-2,5,5,8aα-trimethylnaphthalin-1,4-dion 
• 123218-01-9 (1α,4aβ,8aβ)-(+/-)-1,2,3,4-tetrahydro-1-hydroxy-4,4,7,8a-tetramethyl-(4aH,8aH)-naphthalene-5,8-dione 
• 123218-03-1 rac-5α<<(tert-Butyl)dimethylsilyl>oxy>-4β-ethinyl-1,4,4a,5,6,7,8,8aα-octahydro-4-hydroxy-3,4aα,8,8-tetramethylnaphthalin-1(4H)-on 
• 66428-89-5 (±)-forskolin 
• 64657-20-1 (+/-)-desacetyl forskolin 

Downstream Products

• 64657-21-2 (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-6-(acetyloxy)-3-ethenyldodecahydro-5,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1H-naphtho[2,1-b]pyran-1-one 
• 66575-29-9 forskolin 
• 64657-11-0 C₂₂H₃₄O₇ 
• 121327-87-5 7β-anilinocarbonyloxy-8,13-epoxy-1α,6β,9α-trihydroxylabd-14-en-11-one 
• 120370-90-3 8,13-epoxy-7β-<(4-methoxybenzyloxy)acetoxy>-1α,6β,9α-trihydroxylabd-14-en-11-one 
• 120370-81-2 1α,7β-bis<(4-methoxybenzyloxy)acetoxy>-6β,9α-dihydroxy-8,13-epoxylabd-14-en-11-one 
• 84048-22-6 C₃₄H₄₂N₂O₈ 
• 66428-89-5 (±)-forskolin 
• 144426-73-3 7β-(tert-butyldimethylsiloxy)-8,13-epoxy-6β,9α-dihydroxy-11-oxolabd-14-en-1-α-yl diphenylphosphate 
• 111149-17-8 (Cyclohexyl-methyl-amino)-acetic acid (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-3-vinyl-dodecahydro-benzo[f]chromen-6-yl ester 
• 115076-96-5 C₅₀H₇₁NO₁₄ 
• 115076-81-8 Benzylamino-acetic acid (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-3-vinyl-dodecahydro-benzo[f]chromen-6-yl ester; hydrochloride 
• 115076-86-3 (4-Benzoylamino-piperidin-1-yl)-acetic acid (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-3-vinyl-dodecahydro-benzo[f]chromen-6-yl ester 
• 115076-65-8 (4-Benzoylamino-piperidin-1-yl)-acetic acid (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-3-vinyl-dodecahydro-benzo[f]chromen-5-yl ester 

Relevant articles and documents

Stability of forskolin in lipid emulsions and oil/water partition coefficients

Forskolin (FK), a diterpenoid isolated from Coleus Forskohlii, underwent base-catalyzed hydrolysis, producing 7-deacetyl forskolin. The half-life at pH 7.0 and 25°C was 16 d. Because of its poor solubility in water and degradation, the drug was incorporated in lipid emulsions (soybean oil/water=10.9/89.1 v/v, average diameter of the droplets, 204 nm). No degradation of the drug was found in the lipid emulsion up to 30 d. The distribution of FK in the lipid emulsions was investigated based on a three-phase model which assumes that the drug resides in the oil and water phases and at the oil/water interface. From the determination of bulk oil/water and lipid emulsion partition coefficients, the relative percentages of the drug in the oil droplets, in the aqueous phase and at the interface were 43.3, 4.9 and 51.3%, respectively. This distribution profile seems to be consistent with the improved stability of FK in the lipid emulsions where the drug residing in the oil phase and at the interface is well protected from hydrolysis. The FK lipid emulsions should be given more interest in access to preclinical and clinical tests because the drug was well stabilized in the formulation and the excipients used are acceptable to human subjects.

Retrosynthesis studies with forskolin

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A Concise Synthesis of Forskolin

A 24-step synthesis of (±)-forskolin is presented, which delivered hundred milligram quantities of this complex diterpene in one pass. Transformations key to our approach include: a) a strategic allylic transposition, b) stepwise assembly of a sterically encumbered isoxazole ring, and c) citric acid-modified Upjohn dihydroxylation of a resilient tetrasubstituted olefin. The developed route has exciting potential for the preparation of new forskolin analogues inaccessible by semisynthesis.

Expedient synthetic transformation of ptychantins into Forskolin

Forskolin has been synthesized in 11 steps with a 17% overall yield from ptychantins A and B, which have been isolated from the liverwort Ptychanthus striatus in good yield. The 1α-hydroxy group was furnished by stereoselective reduction of the corresponding carbonyl group by sodium cyanoborohydride. The 9α-hydroxy group was introduced stereoselectively by epoxidation of Δ9,11-enol ether. Georg Thieme Verlag Stuttgart.