Tetrahydropiperin

Names

[ Name ]:
Tetrahydropiperin

[Synonym ]:
1-[5-(1,3-Benzodioxol-5-yl)pentanoyl]piperidine
Tetrahydropiperidine
5-(1,3-Benzodioxol-5-yl)-1-(piperidin-1-yl)pentan-1-one
Tetrahydropiperin
1-Pentanone, 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-
5-(1,3-Benzodioxol-5-yl)-1-(1-piperidinyl)-1-pentanone
Piperidine, 1-[5-(1,3-benzodioxol-5-yl)-1-oxopentyl]-
Cosmoperine
Tetrahydropiperine

Biological Activity

[Description]:

Tetrahydropiperine, a cyclohexyl analogue of piperine, is the first natural aryl pentanamide from Piper longum[1]. Tetrahydropiperine (compound 14) inhibits the cytochrome P450 (CYP) isoform CYP1A1/arylhydrocarbon hydroxylase (AHH; IC50=23 µM)[2].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450

[Target]

CYP1A1:23 μM (IC50)

[References]

[1]. Madhusudhan P, et al. Tetrahydropiperine, the first natural aryl pentanamide from Piper longum. Biochem Syst Ecol. 2001 May;29(5):537-538.

[2]. Koul S, et al. Structure-activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochromeP450 activities. Bioorg Med Chem. 2000 Jan;8(1):251-68.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
469.9±24.0 °C at 760 mmHg

[ Melting Point ]:
41ºC

[ Molecular Formula ]:
C₁₇H₂₃NO₃

[ Molecular Weight ]:
289.369

[ Flash Point ]:
238.0±22.9 °C

[ Exact Mass ]:
289.167786

[ PSA ]:
38.77000

[ LogP ]:
3.67

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.556

[ Storage condition ]:
-20℃

Tetrahydropiperin

Names

Biological Activity

Chemical & Physical Properties

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds