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
Empirical Formula (Hill Notation):
C22H34O5
CAS Number:
Molecular Weight:
378.50
MDL number:
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

assay

≥97%

form

solid

optical activity

α26/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

HC@@12C@H(O)C@H(OC(C)=O)C@@3(C)OC@(C)(CC(=O)C3C@@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

Packaging

1, 5 mg in glass bottle

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 featured on the Adenylyl cyclases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
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.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Daniela Terracciano et al.
Oncology reports, 14(3), 719-722 (2005-08-04)
The expression of sialyl Lewis(a) antigen, also known as Ca 19-9, in colon cancer, normal tissues and LS174T human colon carcinoma cells were studied. In colon adenocarcinoma and cell plasma membranes this antigen is expressed on various glycoproteins with different...
Xunshan Ding et al.
The Journal of pharmacology and experimental therapeutics, 312(2), 849-856 (2004-10-02)
An extract of the plant Coleus forskohlii has been used for centuries in Ayurvedic medicine to treat various diseases such as hypothyroidism, heart disease, and respiratory disorders. Additionally, complex herbal mixtures containing this extract are gaining popularity in United States...
Lili Lu et al.
Journal of cellular physiology, 228(2), 251-257 (2012-06-22)
High blood glucose results in high glucose levels in retina, because GLUT1, the sole glucose transporter between blood and retina, transports more glucose when blood glucose is high. This is the ultimate cause of diabetic retinopathy. Knockdown of GLUT1 by...
Atik Ure et al.
Neuroscience letters, 392(1-2), 10-15 (2005-09-21)
Effects of cAMP-activated protein kinases (PKA) on epileptic activity are at present studied in a model nervous system. Identified neurons in the buccal ganglia of the snail Helix pomatia were recorded with intracellular microelectrodes in a continuously perfused experimental chamber....
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...
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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.
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