Synonym
Tetrahydropiperine, THP
IUPAC/Chemical Name
5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-1-pentanone
InChi Key
APZYKUZPJCQGPP-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H23NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h8-9,12H,1-7,10-11,13H2
SMILES Code
O=C(CCCCC1=CC(OCO2)=C2C=C1)N3CCCCC3
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
289.38
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Kumar D, Rahman Sarkar A, Iqbal Andrabi N, Assim Haq S, Ahmed M, Kumar Shukla S, Ahmed Z, Rai R. Synthesis, characterization, and anti-inflammatory activity of tetrahydropiperine, piperic acid, and tetrahydropiperic acid via down regulation of NF-κB pathway. Cytokine. 2024 Jun;178:156578. doi: 10.1016/j.cyto.2024.156578. Epub 2024 Mar 13. PMID: 38484621.
2: Ren H, Yuan Q, Lu J, Xi S, Liu Y, Yang G, Xie Z, Wang B, Ma L, Fu X, Liu J, Zhang Y. Tetrahydropiperine, a natural alkaloid with neuroprotective effects in ischemic stroke. J Chem Neuroanat. 2024 Mar;136:102397. doi: 10.1016/j.jchemneu.2024.102397. Epub 2024 Feb 7. PMID: 38331229.
3: Chen X, Li Y. Identification of the stable and reactive metabolites of tetrahydropiperine using ultrahigh-performance liquid chromatography combined with diode-array detection and high-resolution mass spectrometry. Rapid Commun Mass Spectrom. 2021 Jan 30;35(2):e8975. doi: 10.1002/rcm.8975. PMID: 33049799.
4: Ahirrao P, Tambat R, Chandal N, Mahey N, Kamboj A, Jain UK, Singh IP, Jachak SM, Nandanwar HS. MsrA Efflux Pump Inhibitory Activity of Piper cubeba L.f. and its Phytoconstituents against Staphylococcus aureus RN4220. Chem Biodivers. 2020 Aug;17(8):e2000144. doi: 10.1002/cbdv.202000144. Epub 2020 Jul 3. PMID: 32449250.
5: Faas L, Venkatasamy R, Hider RC, Young AR, Soumyanath A. In vivo evaluation of piperine and synthetic analogues as potential treatments for vitiligo using a sparsely pigmented mouse model. Br J Dermatol. 2008 May;158(5):941-50. doi: 10.1111/j.1365-2133.2008.08464.x. Epub 2008 Feb 16. PMID: 18284389.
6: Barbieri E Jr, Barreto CB Jr, Ribeiro RC, de Oliveira VH, Freire de Lima ME, Moya-Borja GE. Efeito inseticida de amidas naturais de Piper e do derivado sintético tetraidropiperina sobre Lucilia cuprina (Diptera: Calliphoridae) E Musca domestica (Diptera: Muscidae) [Insecticide effects of natural amides from Piper and of the synthetic derivative tetrahydropiperine on Lucilia cuprina (Diptera: Calliphoridae) and Musca domestica (Diptera: Muscidae)]. Rev Bras Parasitol Vet. 2007 Apr-Jun;16(2):87-91. Portuguese. PMID: 17706010.
7: Madhusudhan P, Vandana KL. Tetrahydropiperine, the first natural aryl pentanamide from Piper longum. Biochem Syst Ecol. 2001 May;29(5):537-538. doi: 10.1016/s0305-1978(00)00083-1. PMID: 11274775.
