66575-29-9 Usage
Description
Forskolin, also known as Coleus forskohlii, is a diterpene compound derived from the roots of the Coleus forskohlii plant. It possesses vasodilating, cardiostimulatory, antioxidant, and anti-inflammatory properties. Forskolin resensitizes cell receptors by activating the enzyme adenylyl cyclase and increasing the intracellular levels of cyclic adenosine monophosphate (cAMP). FORSKOLIN has been found to have various pharmacological applications, including the treatment of hypertension, respiratory disorders, and obesity.
Uses
Used in Pharmaceutical Industry:
Forskolin is used as an adenylate cyclase activator for its ability to modulate adenylyl cyclase enzyme and cAMP levels, which is essential for the proper biological response of cells to hormones, neurotransmitters, and other extracellular signals.
Used in Cardiovascular Applications:
Forskolin is used as a positive inotropic agent and vasodilator for its ability to improve heart function and blood flow, making it beneficial in treating hypertension and other cardiovascular conditions.
Used in Respiratory Applications:
Forskolin is used to treat respiratory disorders due to its bronchodilating and anti-inflammatory properties, which help in reducing inflammation and improving lung function.
Used in Obesity Treatment:
Forskolin is used as a weight loss aid for its ability to stimulate insulin release and reduce hyperglycemia, which can help in managing obesity and related metabolic disorders.
Used in Antiglaucoma Treatment:
Forskolin is used as an antiglaucoma agent for its ability to lower intraocular pressure, which can help in managing glaucoma and preventing vision loss.
Used in Research and Development:
Forskolin is used as a research tool for examining adenylyl cyclase expression, regulation, and G protein signaling, as well as for the purification of adenylate cyclase.
Used in MAP Kinase Inhibition:
Forskolin is used as a MAP kinase inhibitor, which can help in studying and understanding the role of MAP kinases in various cellular processes and diseases.
Biological Activity
Cell-permeable activator of adenylyl cyclase. Hypotensive and vasodilatory agent. Induces neuronal differentiation in stem cells and in several neuroblastoma. Also available as part of the PKA Tocriset? .
Biochem/physiol Actions
Cell permeable: yes
Purification Methods
It is an antihypertensive, a positive ionotropic, a platelet aggregation inhibitor, and it has adenylate cyclase activating properties [Chem Abstr 89 244150 1978, de Souza et al. Med Res Rev 3 201 1983, X-ray: Tandon et al. Indian J Chem 15B 880 1977]. [Beilstein 18/5 V 55.]
References
1) Awad et al (1983) Interactions of forskolin and adenylate cyclase; J. Biol. Chem., 258 2960
2) Bhat et al (1983) The antihypertensive and positive inotropic diterpene forskolin: effects of structural modifications on its activity; J. Med. Chem., 26 486
3) de Souza et al. (1983) Forskolin: a labdane diterpenoid with antihypertensive, positive inotropic, platelet aggregation inhibitory, and adenylate cyclase activating properties; Med. Res. Rev. 3 201
4) Aylwin & White (1992) Forskolin acts as a noncompetitive inhibitor of nicotinic acetylcholine receptors; Mol. Pharmacol. 41 908
5) Insel & Ostrom (2003) Forskolin as a tool for examining adenylyl cyclase expression, regulation, and G protein signaling; Cell Mol. Neurobiol., 23 305
Check Digit Verification of cas no
The CAS Registry Mumber 66575-29-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,6,5,7 and 5 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 66575-29:
(7*6)+(6*6)+(5*5)+(4*7)+(3*5)+(2*2)+(1*9)=159
159 % 10 = 9
So 66575-29-9 is a valid CAS Registry Number.
InChI:InChI=1/C22H34O7/c1-8-19(5)11-14(25)22(27)20(6)13(24)9-10-18(3,4)16(20)15(26)17(28-12(2)23)21(22,7)29-19/h8,13,15-17,24,26-27H,1,9-11H2,2-7H3/t13-,15-,16?,17-,19-,20-,21+,22-/m0/s1
66575-29-9Relevant articles and documents
A Radical-Polar Crossover Annulation to Access Terpenoid Motifs
Thomas, William P.,Schatz, Devon J.,George, David T.,Pronin, Sergey V.
supporting information, p. 12246 - 12250 (2019/08/27)
A new catalytic radical-polar crossover annulation between two unsaturated carbonyl compounds is described. The annulation proceeds under exceptionally mild conditions and provides direct and expedient access to complex terpenoid motifs. Application of this chemistry allows for synthesis of forskolin, a densely functionalized terpenoid, in 14 steps from commercially available material.
Expedient synthetic transformation of ptychantins into Forskolin
Hagiwara, Hisahiro,Tsukagoshi, Masashi,Hoshi, Takashi,Suzuki, Toshio,Hashimoto, Toshihiro,Asakawa, Yoshinori
, p. 929 - 931 (2008/12/22)
Forskolin has been synthesized in 11 steps with a 17% overall yield from ptychantins A and B, which have been isolated from the liverwort Ptychanthus striatus in good yield. The 1α-hydroxy group was furnished by stereoselective reduction of the corresponding carbonyl group by sodium cyanoborohydride. The 9α-hydroxy group was introduced stereoselectively by epoxidation of Δ9,11-enol ether. Georg Thieme Verlag Stuttgart.
Total synthesis of forskolin - Part II
Delpech, Bernard,Calvo, Daniel,Lett, Robert
, p. 1019 - 1022 (2007/10/03)
The further elaboration of the key-intermediate 5 into forskolin 1 has been achieved via two different routes. Key features of this new total synthesis are: 1) the stereospecific formation of the 6β, 7β, 8α-triol via the BF3-Et2O assisted opening of the epoxy carbamate 8; 2) use of the 8α, 11-di-t-butylsilylene ketal for the specific protection of the 6β, 7β-diol, from the tetrol 10(A); two new sequences for the formation of the dihydro-γ-pyrone ring in high overall yield from 23; 4) the stereoselective divinyl cuprate conjugate α-addition on the dihydro-γ-pyrone 16 or 28, in the presence of BF3-Et2o, with the stereochemistry required for forskolin synthesis.