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D3658

1,9-Dideoxyforskolin from Coleus forskohlii

Name: 1,9-Dideoxyforskolin from <I>Coleus forskohlii</I>
Brand: SIGMA

≥97%, solid

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):

C₂₂H₃₄O₅

Numero CAS:

64657-18-7

Peso molecolare:

378.50

Numero MDL:

MFCD00082318

Codice UNSPSC:

41106305

ID PubChem:

24893774

NACRES:

NA.77

Livello qualitativo

200

Saggio

≥97%

Stato

solid

Attività ottica

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

Colore

white to off-white

Solubilità

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.)

Temperatura di conservazione

−20°C

Stringa SMILE

[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
ZKZMDXUDDJYAIB-OJPJTMFRSA-N

Applicazioni

Useful as a negative control for forskolin.

Azioni biochim/fisiol

Biologically inactive forskolin analog. Does not stimulate adenylyl cyclase.

Caratteristiche e vantaggi

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Synthetic transformation of ptychantin into forskolin and 1,9-dideoxyforskolin.

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

Adenylate cyclase and potassium channels are involved in forskolin- and 1,9-dideoxyforskolin-induced inhibition of pregnant rat uterus contractility.

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

Mediation of the cardiac effects of forskolin by specific binding sites.

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

Apoptosis to necrosis switching downstream of apoptosome formation requires inhibition of both glycolysis and oxidative phosphorylation in a BCL-X(L)- and PKB/AKT-independent fashion.

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

Beta1-adrenergic receptors but not beta2-adrenergic or vasopressin receptors regulate K+ secretion in vestibular dark cells of the inner ear.

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 +/-

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