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MedKoo Cat#: 145929 | Name: Piperanine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Piperanine is an alkaloid compound derived from the Piperaceae family, particularly from Piper nigrum (black pepper). It is studied for its potential therapeutic properties, including anti-inflammatory, antioxidant, and antimicrobial effects. The mechanism of action of piperanine involves its ability to modulate various cellular pathways, such as the inhibition of pro-inflammatory enzymes and the reduction of oxidative stress in cells. Additionally, it may enhance the bioavailability of other compounds, potentially making it useful in combination therapies for conditions like infections and inflammatory diseases.

Chemical Structure

Piperanine
Piperanine
CAS#23512-46-1

Theoretical Analysis

MedKoo Cat#: 145929

Name: Piperanine

CAS#: 23512-46-1

Chemical Formula: C17H21NO3

Exact Mass: 287.1500

Molecular Weight: 287.36

Elemental Analysis: C, 71.06; H, 7.37; N, 4.87; O, 16.70

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Piperanine;
IUPAC/Chemical Name
(E)-5-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)pent-2-en-1-one
InChi Key
QHWOFMXDKFORMO-XVNBXDOJSA-N
InChi Code
1S/C17H21NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h3,7-9,12H,1-2,4-6,10-11,13H2/b7-3+
SMILES Code
O=C(\C=C\CCC1=CC=C2OCOC2=C1)N3CCCCC3
Appearance
To be determined
Purity
>98% (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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 287.36 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.

Recalculate based on batch purity %
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: Liao CP, Dong SQ, Liu YL, Enirile, Gao Y, Fan HR, Cai QJ, Dai JG, Tu Y. [Intestinal absorption components and absorption characteristics of Wuwei Qingzhuo San by everted intestinal sac models]. Zhongguo Zhong Yao Za Zhi. 2024 Jan;49(2):509-517. Chinese. doi: 10.19540/j.cnki.cjcmm.20230728.201. PMID: 38403326. 2: Okumura Y, Narukawa M, Iwasaki Y, Ishikawa A, Matsuda H, Yoshikawa M, Watanabe T. Activation of TRPV1 and TRPA1 by black pepper components. Biosci Biotechnol Biochem. 2010;74(5):1068-72. doi: 10.1271/bbb.90964. Epub 2010 May 7. PMID: 20460725. 3: Zhen D, Na RS, Wang Y, Bai X, Fu DN, Wei CX, Liu MJ, Yu LJ. Cardioprotective effect of ethanol extracts of Sugemule-3 decoction on isoproterenol-induced heart failure in Wistar rats through regulation of mitochondrial dynamics. J Ethnopharmacol. 2022 Jun 28;292:114669. doi: 10.1016/j.jep.2021.114669. Epub 2021 Sep 29. PMID: 34600079. 4: Yu L, Hu X, Xu R, Ba Y, Chen X, Wang X, Cao B, Wu X. Amide alkaloids characterization and neuroprotective properties of Piper nigrum L.: A comparative study with fruits, pericarp, stalks and leaves. Food Chem. 2022 Jan 30;368:130832. doi: 10.1016/j.foodchem.2021.130832. Epub 2021 Aug 10. PMID: 34474242. 5: Mizumoto T, Nakano F, Nishizaki Y, Masumoto N, Sugimoto N. [Quantitative Analysis of Piperine and the Derivatives in Long Pepper Extract by HPLC Using Relative Molar Sensitivity]. Shokuhin Eiseigaku Zasshi. 2019;60(5):134-143. Japanese. doi: 10.3358/shokueishi.60.134. PMID: 31956239. 6: 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. 7: Matsuda H, Ninomiya K, Morikawa T, Yasuda D, Yamaguchi I, Yoshikawa M. Protective effects of amide constituents from the fruit of Piper chaba on D-galactosamine/TNF-alpha-induced cell death in mouse hepatocytes. Bioorg Med Chem Lett. 2008 Mar 15;18(6):2038-42. doi: 10.1016/j.bmcl.2008.01.101. Epub 2008 Jan 31. PMID: 18289853. 8: Ekanem AP, Wang M, Simon JE, Obiekezie AI, Morah F. In vivo and in vitro activities of the seed extract of Piper guineense Schum. and Thonn. against skin and gill monogenean parasites of gold fish (Carassius auratus auratus). Phytother Res. 2004 Oct;18(10):793-7. doi: 10.1002/ptr.1550. PMID: 15551399. 9: Liu HL, Luo R, Chen XQ, Ba YY, Zheng L, Guo WW, Wu X. Identification and simultaneous quantification of five alkaloids in Piper longum L. by HPLC-ESI- MS(n) and UFLC-ESI-MS/MS and their application to Piper nigrum L. Food Chem. 2015 Jun 15;177:191-6. doi: 10.1016/j.foodchem.2015.01.033. Epub 2015 Jan 9. PMID: 25660876. 10: Morikawa T, Matsuda H, Yamaguchi I, Pongpiriyadacha Y, Yoshikawa M. New amides and gastroprotective constituents from the fruit of Piper chaba. Planta Med. 2004 Feb;70(2):152-9. doi: 10.1055/s-2004-815493. PMID: 14994194. 11: Stöhr JR, Xiao PG, Bauer R. Constituents of Chinese Piper species and their inhibitory activity on prostaglandin and leukotriene biosynthesis in vitro. J Ethnopharmacol. 2001 May;75(2-3):133-9. doi: 10.1016/s0378-8741(00)00397-4. PMID: 11297843. 12: Xu RR, Liu HL, Chen XQ, Ba YY, Wang X, Wu X. [Identify metabolites of Piper longum alkaloids in feces and urine of rat by HPLC-FT-MS]. Zhongguo Zhong Yao Za Zhi. 2018 May;43(9):1798-1805. Chinese. doi: 10.19540/j.cnki.cjcmm.20180305.003. PMID: 29902888. 13: Joshi T, Joshi T, Sharma P, Chandra S, Pande V. Molecular docking and molecular dynamics simulation approach to screen natural compounds for inhibition of Xanthomonas oryzae pv. Oryzae by targeting peptide deformylase. J Biomol Struct Dyn. 2021 Feb;39(3):823-840. doi: 10.1080/07391102.2020.1719200. Epub 2020 Jan 30. PMID: 31965918. 14: Wu S, Sun C, Pei S, Lu Y, Pan Y. Preparative isolation and purification of amides from the fruits of Piper longum L. by upright counter-current chromatography and reversed-phase liquid chromatography. J Chromatogr A. 2004 Jun 25;1040(2):193-204. doi: 10.1016/j.chroma.2004.03.056. PMID: 15230526. 15: Xu R, Zhao W, Yu L, Chen Q, Hu X, Ba Y, Chen X, Wang X, Wu X. A selective and sensitive UFLC-MS/MS method for the simultaneous determination of five alkaloids from Piper longum L. and its application in the pharmacokinetic study of 6-OHDA-induced Parkinson's disease rats. RSC Adv. 2019 Nov 12;9(63):37082-37091. doi: 10.1039/c9ra06325k. PMID: 35539049; PMCID: PMC9075506. 16: Friedman M, Levin CE, Lee SU, Lee JS, Ohnisi-Kameyama M, Kozukue N. Analysis by HPLC and LC/MS of pungent piperamides in commercial black, white, green, and red whole and ground peppercorns. J Agric Food Chem. 2008 May 14;56(9):3028-36. doi: 10.1021/jf703711z. Epub 2008 Apr 3. PMID: 18386929. 17: Wiwattanawanichakun P, Ratwatthananon A, Poonsri W, Yooboon T, Pluempanupat W, Piyasaengthong N, Nobsathian S, Bullangpoti V. The Possibility of Using Isolated Alkaloid Compounds and Crude Extracts of Piper retrofractum (Piperaceae) as Larvicidal Control Agents for Culex quinquefasciatus (Diptera: Culicidae) Larvae. J Med Entomol. 2018 Aug 29;55(5):1231-1236. doi: 10.1093/jme/tjy082. PMID: 29796657. 18: Guo K, Peng M, Tong C, Shi S, Liu Y. Direct from solid natural products to pure compounds in a single step: Coupling online extraction with high-speed counter-current chromatography. J Sep Sci. 2018 Sep;41(18):3607-3613. doi: 10.1002/jssc.201800360. Epub 2018 Sep 10. PMID: 30073789.