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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

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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’.

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P d'Alcantara et al.
Biophysical journal, 77(1), 204-216 (1999-07-02)
The activity of the voltage-gated Na+ channel is subjected to modulation through covalent modifications. It has been previously shown that brain Na+ currents are reduced following the activation of the protein kinase A (PKA) pathway, but the effect of the
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
C Y Liu et al.
Brain research, 826(2), 253-269 (1999-05-04)
The aims of this study were to improve insight into cAMP signaling in myenteric neurons and glia and identify the adenylyl cyclase (AC) isoforms expressed in myenteric ganglia of the guinea-pig small intestine. An increase in the intracellular cAMP levels
E X Albuquerque et al.
FEBS letters, 199(1), 113-120 (1986-04-07)
Forskolin, an activator of adenylate cyclase, and its analogs were studied on the nicotinic acetylcholine receptor-ion channel complex (AChR) of rat and frog skeletal muscles. At nanomolar concentrations, forskolin caused desensitization of the AChR located at the junctional region of
M Morales-Mulia et al.
Biochimica et biophysica acta, 1496(2-3), 252-260 (2000-04-20)
The role of the phospholemman (PLM) on the efflux of taurine and chloride induced by swelling was studied in HEK293 cells overexpressing stable transfected PLM. PLM, a substrate for protein kinases C and A, is a protein that induces an
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