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MedKoo Cat#: 584911 | Name: Pellitorine

Description:

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

Pellitorine is an extract of Tetradium daniellii, and an antagonist of the ion channel TRPV1.

Chemical Structure

Pellitorine
Pellitorine
CAS#18836-52-7

Theoretical Analysis

MedKoo Cat#: 584911

Name: Pellitorine

CAS#: 18836-52-7

Chemical Formula: C14H25NO

Exact Mass: 223.1936

Molecular Weight: 223.36

Elemental Analysis: C, 75.28; H, 11.28; N, 6.27; O, 7.16

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
AI3-19560; Pellitorin; Pellitorine
IUPAC/Chemical Name
2,4-Decadienamide, N-isobutyl-, (E,E)-
InChi Key
MAGQQZHFHJDIRE-BNFZFUHLSA-N
InChi Code
InChI=1S/C14H25NO/c1-4-5-6-7-8-9-10-11-14(16)15-12-13(2)3/h8-11,13H,4-7,12H2,1-3H3,(H,15,16)/b9-8+,11-10+
SMILES Code
CCCCC/C=C/C=C/C(NCC(C)C)=O
Appearance
Solid powder
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
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 223.36 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: Rohm B, Riedel A, Ley JP, Widder S, Krammer GE, Somoza V. Capsaicin, nonivamide and trans-pellitorine decrease free fatty acid uptake without TRPV1 activation and increase acetyl-coenzyme A synthetase activity in Caco-2 cells. Food Funct. 2015 Jan;6(1):173-85. doi: 10.1039/c4fo00435c. Epub 2014 Nov 25. PubMed PMID: 25422952. 2: Veryser L, Taevernier L, Roche N, Peremans K, Burvenich C, De Spiegeleer B. Quantitative transdermal behavior of pellitorine from Anacyclus pyrethrum extract. Phytomedicine. 2014 Dec 15;21(14):1801-7. doi: 10.1016/j.phymed.2014.08.015. Epub 2014 Nov 11. PubMed PMID: 25481393. 3: Lee W, Ku SK, Min BW, Lee S, Jee JG, Kim JA, Bae JS. Vascular barrier protective effects of pellitorine in LPS-induced inflammation in vitro and in vivo. Fitoterapia. 2014 Jan;92:177-87. doi: 10.1016/j.fitote.2013.11.006. Epub 2013 Nov 18. PubMed PMID: 24262867. 4: Lieder B, Zaunschirm M, Holik AK, Ley JP, Hans J, Krammer GE, Somoza V. The Alkamide trans-Pellitorine Targets PPARγ via TRPV1 and TRPA1 to Reduce Lipid Accumulation in Developing 3T3-L1 Adipocytes. Front Pharmacol. 2017 May 31;8:316. doi: 10.3389/fphar.2017.00316. eCollection 2017. PubMed PMID: 28620299; PubMed Central PMCID: PMC5449966. 5: Veryser L, Bracke N, Wynendaele E, Joshi T, Tatke P, Taevernier L, De Spiegeleer B. Quantitative In Vitro and In Vivo Evaluation of Intestinal and Blood-Brain Barrier Transport Kinetics of the Plant N-Alkylamide Pellitorine. Biomed Res Int. 2016;2016:5497402. doi: 10.1155/2016/5497402. Epub 2016 Jul 4. PubMed PMID: 27493960; PubMed Central PMCID: PMC4947679. 6: Ngo QM, Tran PT, Tran MH, Kim JA, Rho SS, Lim CH, Kim JC, Woo MH, Choi JS, Lee JH, Min BS. Alkaloids from Piper nigrum Exhibit Antiinflammatory Activity via Activating the Nrf2/HO-1 Pathway. Phytother Res. 2017 Apr;31(4):663-670. doi: 10.1002/ptr.5780. Epub 2017 Feb 10. PubMed PMID: 28185326. 7: Oláh Z, Rédei D, Pecze L, Vizler C, Jósvay K, Forgó P, Winter Z, Dombi G, Szakonyi G, Hohmann J. Pellitorine, an extract of Tetradium daniellii, is an antagonist of the ion channel TRPV1. Phytomedicine. 2017 Oct 15;34:44-49. doi: 10.1016/j.phymed.2017.06.006. Epub 2017 Jul 3. PubMed PMID: 28899508. 8: Perumalsamy H, Kim JR, Oh SM, Jung JW, Ahn YJ, Kwon HW. Novel histopathological and molecular effects of natural compound pellitorine on larval midgut epithelium and anal gills of Aedes aegypti. PLoS One. 2013 Nov 18;8(11):e80226. doi: 10.1371/journal.pone.0080226. eCollection 2013. PubMed PMID: 24260359; PubMed Central PMCID: PMC3832413. 9: Skaf J, Hamarsheh O, Berninger M, Balasubramanian S, Oelschlaeger TA, Holzgrabe U. Improving anti-trypanosomal activity of alkamides isolated from Achillea fragrantissima. Fitoterapia. 2018 Mar;125:191-198. doi: 10.1016/j.fitote.2017.11.001. Epub 2017 Nov 3. PubMed PMID: 29108932. 10: Ee GC, Lim CM, Rahmani M, Shaari K, Bong CF. Pellitorine, a potential anti-cancer lead compound against HL6 and MCT-7 cell lines and microbial transformation of piperine from Piper Nigrum. Molecules. 2010 Apr 5;15(4):2398-404. doi: 10.3390/molecules15042398. PubMed PMID: 20428051; PubMed Central PMCID: PMC6257300. 11: Walker J, Ley JP, Schwerzler J, Lieder B, Beltran L, Ziemba PM, Hatt H, Hans J, Widder S, Krammer GE, Somoza V. Nonivamide, a capsaicin analogue, exhibits anti-inflammatory properties in peripheral blood mononuclear cells and U-937 macrophages. Mol Nutr Food Res. 2017 Feb;61(2). doi: 10.1002/mnfr.201600474. Epub 2016 Nov 15. PubMed PMID: 27666931. 12: Kim SI, Ahn YJ. Larvicidal activity of lignans and alkaloid identified in Zanthoxylum piperitum bark toward insecticide-susceptible and wild Culex pipiens pallens and Aedes aegypti. Parasit Vectors. 2017 May 4;10(1):221. doi: 10.1186/s13071-017-2154-0. PubMed PMID: 28472971; PubMed Central PMCID: PMC5418860. 13: Obst K, Lieder B, Reichelt KV, Backes M, Paetz S, Geißler K, Krammer G, Somoza V, Ley JP, Engel KH. Sensory active piperine analogues from Macropiper excelsum and their effects on intestinal nutrient uptake in Caco-2 cells. Phytochemistry. 2017 Mar;135:181-190. doi: 10.1016/j.phytochem.2016.12.016. Epub 2017 Jan 5. PubMed PMID: 28065397. 14: Ku SK, Lee IC, Kim JA, Bae JS. Anti-septic effects of pellitorine in HMGB1-induced inflammatory responses in vitro and in vivo. Inflammation. 2014 Apr;37(2):338-48. doi: 10.1007/s10753-013-9745-5. PubMed PMID: 24077682. 15: Ku SK, Lee IC, Kim JA, Bae JS. Antithrombotic activities of pellitorine in vitro and in vivo. Fitoterapia. 2013 Dec;91:1-8. doi: 10.1016/j.fitote.2013.08.004. Epub 2013 Aug 22. PubMed PMID: 23973654. 16: Althaus JB, Kaiser M, Brun R, Schmidt TJ. Antiprotozoal activity of Achillea ptarmica (Asteraceae) and its main alkamide constituents. Molecules. 2014 May 20;19(5):6428-38. doi: 10.3390/molecules19056428. PubMed PMID: 24853616; PubMed Central PMCID: PMC6271219. 17: JACOBSON M. The structure of pellitorine. J Am Chem Soc. 1949 Jan;71(1):366. PubMed PMID: 18108975. 18: Obst K, Paetz S, Backes M, Reichelt KV, Ley JP, Engel KH. Evaluation of unsaturated alkanoic acid amides as maskers of epigallocatechin gallate astringency. J Agric Food Chem. 2013 May 8;61(18):4242-9. doi: 10.1021/jf400455z. Epub 2013 Apr 24. PubMed PMID: 23582039. 19: CROMBIE L, HARPER SH. Synthesis of a physiologically active compound of the pellitorine structure. Nature. 1949 Dec 17;164(4181):1053. PubMed PMID: 15408072. 20: RAPHAEL RA, SONDHEIMER F. Synthesis of geometrical isomers of pellitorine and herculin. Nature. 1949 Oct 22;164(4173):707. PubMed PMID: 15406836.