Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

D3658

Sigma-Aldrich

1,9-Dideoxyforskolin from Coleus forskohlii

≥97%, solid

Synonym(s):

7β-Acetoxy-6β-hydroxy-8,13-epoxy-labd-14-en-11-one

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C22H34O5
CAS Number:
64657-18-7
Molecular Weight:
378.50
MDL number:
MFCD00082318
UNSPSC Code:
41106305
PubChem Substance ID:
24893774
NACRES:
NA.77

Assay

≥97%

form

solid

optical activity

[α]26/D +93.6°, c = 6.12 in chloroform(lit.)

color

white to off-white

solubility

methanol: 28 mg/mL(lit.)
DMSO: 3 mg/mL(lit.)
chloroform: 50 mg/mL
ethanol: 6.6 mg/mL(lit.)
dilute aqueous acid and base: insoluble(lit.)

storage temp.

−20°C

SMILES string

[H][C@@]12[C@H](O)[C@H](OC(C)=O)[C@@]3(C)O[C@](C)(CC(=O)C3[C@@]1(C)CCCC2(C)C)C=C

InChI

1S/C22H34O5/c1-8-20(5)12-14(24)16-21(6)11-9-10-19(3,4)17(21)15(25)18(26-13(2)23)22(16,7)27-20/h8,15-18,25H,1,9-12H2,2-7H3/t15-,16?,17-,18-,20-,21+,22-/m0/s1

InChI key

ZKZMDXUDDJYAIB-OJPJTMFRSA-N

Application

Useful as a negative control for forskolin.

Biochem/physiol Actions

Biologically inactive forskolin analog. Does not stimulate adenylyl cyclase.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Adenylyl cyclases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Hisahiro Hagiwara et al.
The Journal of organic chemistry, 71(12), 4619-4624 (2006-06-06)
Forskolin (1), a highly oxygenated labdane diterpenoid and an activator of adenylate cyclase, has been synthesized in 12 steps and 12% overall yield from ptychantin A (4), which has been isolated from liverwort Ptychanthus striatus in good yield. The 1alpha-hydroxy
Y P Vedernikov et al.
American journal of obstetrics and gynecology, 182(3), 620-624 (2000-03-30)
We sought to study the contribution of potassium channels in the effect of forskolin and 1,9-dideoxyforskolin on uterine contractility in the pregnant rat. Rings taken from the middle portions of uterine horns from rats at 16 days of gestation were
K Schmidt et al.
Journal of cardiovascular pharmacology, 13(3), 353-360 (1989-03-01)
The effects of forskolin and seven derivatives on cardiac functions were investigated by using the Langendorff technique and the results compared with the respective potencies obtained from adenylate cyclase and binding studies. In the isolated heart, forskolin increased all parameters
D Gramaglia et al.
Cell death and differentiation, 11(3), 342-353 (2004-01-10)
Human T-lymphoma Jurkat cells treated with several intrinsic death stimuli readily undergo a stepwise apoptotic program. Treatment with 1,9-dideoxyforskolin (ddFSK), an inactive analogue of the adenylate cyclase activator forskolin, induces necrotic cell death and switches to necrosis the response to
P Wangemann et al.
The Journal of membrane biology, 170(1), 67-77 (1999-07-10)
Receptors were identified pharmacologically in functional studies where K+ secretion was monitored as transepithelial current (Isc). Further, receptors were identified as transcripts by cloning and sequencing of reverse-transcriptase polymerase chain reaction (RT-PCR) products. Isc under control conditions was 796 +/-
View All Related Papers

Articles

Discover Bioactive Small Molecules for Cyclic Nucleotides

Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service