64657-21-2

Basic information

• Product Name: 6-ACETYL-7-DEACETYLFORSKOLIN
• Synonyms: 6-ACETYL-7-DEACETYLFORSKOLIN;6BETA-ACETOXY-1ALPHA,7BETA,9ALPHA-TRIHYDROXY-8,13-EPOXY-LABD-14-EN-11-ONE;6BETA-ACETOXY-8,13-EPOXY-1ALPHA,7BETA,9ALPHA-TRIHYDROXY-LABD-14-EN-11-ONE;FORSKOLIN, 6-ACETYL-7-DEACETYL-;ISOFORSKOLIN;6-ACETYL-7-DEACETYLFORSKOLIN FROMCOLEUS FORSKOHLII;6β-acetoxy-1α,7β,9α-trihydroxy-8,13-epoxy-labd-14-en-11-one;Isoforskolin, 6β-Acetoxy-1α,7β,9α-trihydroxy-8,13-epoxy-labd-14-en-11-one
• CAS NO: 64657-21-2
• Molecular Formula: C₂₂H₃₄O₇
• Molecular Weight: 410.5
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Diterpenoids
• Mol File: 64657-21-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 220-222 °C(Solv: chloroform (67-66-3); methanol (67-56-1))
• Boiling Point: 524.456°C at 760 mmHg
• Flash Point: 173.643°C
• Appearance: /
• Density: 1.239g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.552
• Storage Temp.: −20°C
• PKA: 11.03±0.70(Predicted)
• CAS DataBase Reference: 6-ACETYL-7-DEACETYLFORSKOLIN(CAS DataBase Reference)
• NIST Chemistry Reference: 6-ACETYL-7-DEACETYLFORSKOLIN(64657-21-2)
• EPA Substance Registry System: 6-ACETYL-7-DEACETYLFORSKOLIN(64657-21-2)

Safety Data

• Hazard Codes: Xn
• Statements: 21
• Safety Statements: 36
• WGK Germany: 3
• Hazardous Substances Data: 64657-21-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 64657-21-2 differently. You can refer to the following data:
1. Iso-Forskolin is a byproduct in the synthesis of 9-Deoxyforskolin (D239935) from Coleus forskohlii, which is an adenylyl cyclase isoform activator; Antihypertensive.
2. 6-Acetyl-7-deacetylforskolin is a bioactive constituents from the medical plant, Coleus forskohlii. Also, it has anticancer and glucosidase inhibition activities.

General Description

This substance is supplied with certified chromatographic purity. The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

InChI:InChI=1/C22H34O7/c1-8-19(5)11-14(25)22(27)20(6)13(24)9-10-18(3,4)16(20)15(28-12(2)23)17(26)21(22,7)29-19/h8,13,15-17,24,26-27H,1,9-11H2,2-7H3/t13-,15-,16-,17-,19-,20-,21+,22-/m0/s1

Upstream product

• 64657-20-1 7-deacetyl forskolin 
• 75-36-5 acetyl chloride 
• 66575-29-9 forskolin 
• 1055308-36-5 forskolin 
• 1055308-35-4 7-desacetylforskolin 
• 93108-59-9 (3aS,3bR,5R,7aS,7bR,8S,11bS)-2-Ethoxy-7a,8-dihydroxy-2,3b,5,7b,11,11-hexamethyl-5-vinyl-dodecahydro-1,3,4-trioxa-cyclopenta[l]phenanthren-7-one 

Downstream Products

• 81873-08-7 6-O-acetylforskolin 

Relevant articles and documents

Regioselective acetylation of 7-deacetylforskolin with 11C-acetyl chloride

Reaction conditions were studied to control the acetylating position on 7-deacetylforskolin using [11C]acetyl chloride. In a preliminary study using non-labeled acetyl chloride, pyridine, lutidine, triethylamine, N,N-diisopropylethylamine, dimethylaminopyridine (DMAP) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were tested as the base in the acetylation. Pyridine was effective in selective acetylation to yield forskolin in any solvent, and DBU was effective for 1-acetyl-7-deacetylforskolin. Among toluene, dichloromethane and dichloroethane, toluene was the most suitable as the solvent for the selective acetylation of the 7-OH group to give forskolin with any base. In the selectivity of acetylation with [11C]acetyl chloride, more [11C]forskolin was obtained than [11C]1-acetyl-7-deacetylforskolin (70:30) in the presence of pyridine in toluene. [11C]1-acetyl-7-deacetylforskolin was preferentially synthesized with DBU in dichloromethane, and the ratio of [11C]1-acetyl-7-deacetylforskolin to [11C]forskolin was 98:2. For the yield of the [11C]acetylated product, DBU in dichloromethane was also suitable to obtain [11C]1-acetyl-7-deacetylforskolin. However, that of pyridine in toluene did not confer any advantages upon the yield of [11C]forskolin compared with DMAP in toluene.

IDENTITY OF COLEONOL WITH FORSKOLIN: STUCTURE REVISION OF A BASE-CATALYSED REARRANGEMENT PRODUCT

The identity of coleonol and forskolin is shown through structure revision of a rearrangement product isolated earlier from coleonol and is confirmed by direct comparison of authentic coleonol with forskolin 1; in addition, coleonol-B should correctly represented by structure 4.