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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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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.
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
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
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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