Forskolin Chemical Properties

Melting point:

282-232 °C

Boiling point:

520℃

alpha 

D25 -26.19° (c = 1.68 in CHCl3)

Density 

1.23

refractive index 

1.5300 (estimate)

Flash point:

172℃

storage temp. 

room temp

solubility 

DMSO: 5 mg/mL stable at least 6 months at room temperature

form 

powder

pka

11.00±0.70(Predicted)

color 

off-white

Water Solubility 

Soluble in ethanol, dimethylsulfoxide and chloroform. Insolule in water.

λmax

305nm(lit.)

Merck 

14,2476

BRN 

1692716

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 4 months.

InChIKey

OHCQJHSOBUTRHG-KGGHGJDLSA-N

LogP

2.406 (est)

CAS DataBase Reference

66575-29-9

Safety Information

Hazard Codes 

Xn

Risk Statements 

21

Safety Statements 

22-36/37

WGK Germany 

3

RTECS 

QL6150000

F 

10-21

HS Code 

29329990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

Forskolin Usage And Synthesis

Description

Forskolin (66575-29-9) is a widely used adenylate cyclase activator.1 Forskolin also is a positive inotropic agent, vasodilator and induces platelet activation among other activities.2-5

Chemical Properties

Colorless Crystalline Solid

Uses

Forskolin is a diterpene isolated from Coleus forskohlii, possessing vasodilating and cardiostimulatory properties. Forskolin resensitizes cell receptors by activating the enzyme adenylyl cyclase and increasing the intracellular levels of cAMP.

Uses

glucocorticoid, antiinflammatory

Uses

adenylate cyclase activator, antiglaucoma, hypotensive, vasodilator

Uses

Cyclic AMP (cAMP) is an important signal carrier necessary for the proper biological response of cells to hormones, neurotransmitters, and other extracellular signals Forskolin is a naturally occurring diterpene that is produced by the Indian Coleus plant (C. forskohlii). It directly activates adenylyl cyclase through its catalytic subunit and is commonly used to raise levels of cAMP in a wide variety of intact cells and tissue preparations. Forskolin binds to adenylyl cyclase in membranes from stably transfected Sf9 cells expressing type 1 adenylyl cyclase with an IC50 value of 41 nM and demonstrates an EC50 value of 0.5 μM in an activation assay assessing formation of cAMP from ATP. Forskolin also interacts with glucose transporters and certain ion channels and has been used for examining adenylyl cyclase expression, regulation, and G protein signaling.[Cayman Chemical]

Uses

An adenylate cyclase activator and MAP kinase inhibitor

Uses

In purification of adenylate cyclase.

Definition

ChEBI: Forskolin is a labdane diterpenoid isolated from the Indian Coleus plant. It has a role as a plant metabolite, an anti-HIV agent, a protein kinase A agonist, an adenylate cyclase agonist, an antihypertensive agent and a platelet aggregation inhibitor. It is a labdane diterpenoid, an acetate ester, an organic heterotricyclic compound, a triol, a cyclic ketone and a tertiary alpha-hydroxy ketone.

General Description

Forskolin, present predominantly in the root of Coleus forskohlii plant, is a potential pharmacological compound. It is used for treating hypertension, respiratory disorders and obesity. Forskolin is a diterpenoid capable of modulating adenylate cyclase enzyme and cyclic adenosine monophosphate (cAMP) levels. Engineering forskolin biosynthetic pathway caters its commercial production for pharmacological use. Forskolin has antioxidant and anti-inflammatory property and reduces hyperglycemia by stimulating insulin release. Forskolin promotes differentiation of hepatoma HepaRG cells and activates farnesoid X receptor (FXR) and pregnane X receptor(PXR).

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

storage

-20°C (desiccate)

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

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