Kahweol

Modify Date: 2024-01-08 18:41:48

Kahweol Structure
Kahweol structure
Common Name Kahweol
CAS Number 6894-43-5 Molecular Weight 314.419
Density 1.3±0.1 g/cm3 Boiling Point 476.6±45.0 °C at 760 mmHg
Molecular Formula C20H26O3 Melting Point 88-90 °C
MSDS N/A Flash Point 242.0±28.7 °C

 Use of Kahweol


Kahweol is one of the consituents of the coffee from Coffea Arabica with anti-inflammatory anti-angiogenic, and anti-cancerous activities. Kahweol inhibits adipogenesis and increase glucose uptake by AMP-activated protein kinase (AMPK) activation. Kahweol induces apoptosis.

 Names

Name kahweol
Synonym More Synonyms

 Kahweol Biological Activity

Description Kahweol is one of the consituents of the coffee from Coffea Arabica with anti-inflammatory anti-angiogenic, and anti-cancerous activities. Kahweol inhibits adipogenesis and increase glucose uptake by AMP-activated protein kinase (AMPK) activation. Kahweol induces apoptosis.
Related Catalog
Target

AMPK; adipogenesis; apoptosis[1]

In Vitro Kahweol (20-40 μM; 24 hours) decreases TGF-β-induced CTGF protein expression in AML12 and LX2 cells[1]. Kahweol (20-40 μM; 1 hour) decreases TGF-β-induced phospho-Smad2/3 expression in AML12 cells, but does not affect expression in LX2 cells[1]. Kahweol (20-40 μM) significantly decreased TGF-β-stimulated phospho-ERK and JNK expression in primary hepatocytes only[1]. kahweol (0-25 μg/ml; 6-24 hours) increased the phosphorylation of AMPK and its downstream target Acetyl-CoA carboxylase (ACC) in a time-dependent manner in 3T3-L1 cells[2]. kahweol (0-25 μg/ml) significantly affects protein expression of PPARγ, C/EBPα, FABP4, and FASN, that regulate adipocyte differentiation and lipid metabolism[2]. Western Blot Analysis[2] Cell Line: 3T3-L1 cells Concentration: 0, 5, 10, 25 μg/ml Incubation Time: Result: Reduced PPARγ, C/EBPα, FABP4, and FASN expression in a dose-dependent manner.
References

[1]. Seo HY, et al. Kahweol decreases hepatic fibrosis by inhibiting the expression of connective tissue growth factor via the transforming growth factor-beta signaling pathway. Oncotarget. 2017 Aug 1;8(50):87086-87094.

[2]. Baek JH, et al. Kahweol inhibits lipid accumulation and induces Glucose-uptake through activation of AMP-activated protein kinase (AMPK). BMB Rep. 2017 Nov;50(11):566-571.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 476.6±45.0 °C at 760 mmHg
Melting Point 88-90 °C
Molecular Formula C20H26O3
Molecular Weight 314.419
Flash Point 242.0±28.7 °C
Exact Mass 314.188202
PSA 53.60000
LogP 3.38
Vapour Pressure 0.0±1.3 mmHg at 25°C
Index of Refraction 1.623

 Synthetic Route

~97%

Kahweol Structure

Kahweol

CAS#:6894-43-5

Literature: Corey, E. J.; Xiang, Yi Bin Tetrahedron Letters, 1987 , vol. 28, # 45 p. 5403 - 5406

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Kahweol Structure

Kahweol

CAS#:6894-43-5

Literature: Tetrahedron Letters, , vol. 28, # 45 p. 5403 - 5406

~%

Kahweol Structure

Kahweol

CAS#:6894-43-5

Literature: Tetrahedron Letters, , vol. 28, # 45 p. 5403 - 5406

~%

Kahweol Structure

Kahweol

CAS#:6894-43-5

Literature: Tetrahedron Letters, , vol. 28, # 45 p. 5403 - 5406

~%

Kahweol Structure

Kahweol

CAS#:6894-43-5

Literature: Tetrahedron Letters, , vol. 28, # 45 p. 5403 - 5406

 Synonyms

(1S,4S,12S,13R,16R,17R)-17-(Hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0.0.0]nonadeca-5(9),6,10-trien-17-ol
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