Olvanil | CAS#58493-49-5 | TRPV1 receptor agonist

MedKoo Cat#: 561417 | Name: Olvanil

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Description:

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

Olvanil is a TRPV1 receptor agonist. Olvanil is also a capsaicin analog, but it is non-noxious and lacks capsaicin's pungency and CGRP release potential. Ina study, Olvanil was seen to significantly induce Neu-1 sialidase activity in a dose-dependent fashion in RAW-Blue, PANC-1, and SW-620 cells.

Chemical Structure

Olvanil

CAS#58493-49-5

Theoretical Analysis

MedKoo Cat#: 561417

Name: Olvanil

CAS#: 58493-49-5

Chemical Formula: C26H43NO3

Exact Mass: 417.3243

Molecular Weight: 417.63

Elemental Analysis: C, 74.78; H, 10.38; N, 3.35; O, 11.49

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 480.00
25mg	USD 685.00
50mg	USD 1,030.00

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Synonym

Olvanil; Vanillyloleamide; Olvanilo; Olvanilum;

IUPAC/Chemical Name

(Z)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]octadec-9-enamide

InChi Key

OPZKBPQVWDSATI-KHPPLWFESA-N

InChi Code

InChI=1S/C26H43NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26(29)27-22-23-19-20-24(28)25(21-23)30-2/h10-11,19-21,28H,3-9,12-18,22H2,1-2H3,(H,27,29)/b11-10-

SMILES Code

CCCCCCCC/C=C\CCCCCCCC(NCC1=CC=C(O)C(OC)=C1)=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

>2 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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Olvanil (NE-19550) is an analgesic and an agonist of transient receptor potential vanilloid type 1 (TRPV1) channels with an EC50 of 0.7 nM.

In vitro activity:

This study reports that olvanil is a stable and potent inhibitor of AEA facilitated transport into rat basophilic leukemia (RBL-2H3) cells. Olvanil blocked both the uptake and the hydrolysis of [14C]AEA by intact RBL-2H3 cells (IC50 = 9 microM), while capsaicin and pseudocapsaicin (N-vanillyl-nonanamide) were much less active. Olvanil was more potent than previously reported inhibitors of AEA facilitated transport, i.e. phloretin (IC50 = 80 microM), AM404 (12.9% inhibition at 10 microM) or oleoylethanolamide (27.5% inhibition at 10 microM). Reference: FEBS Lett. 1998 Oct 9;436(3):449-54. https://pubmed.ncbi.nlm.nih.gov/9801167/

In vivo activity:

Based on the results obtained under in-vitro conditions, brain metastatic breast carcinoma cells (4TBM) implanted orthotopically into the mammary-pad of Balb-c mice followed by olvanil treatment (i.p.). Olvanil dose-dependently activated sensory nerve fibers and markedly suppressed lung and liver metastasis without altering the growth of primary tumors. Olvanil (5 mg/kg) systemically increased T cell count, enhanced intra-tumoral recruitment of CD8+ T cells and increased IFN-γ response to irradiated cancer cells and Con-A. Reference: Life Sci. 2022 Feb 15;291:120305. https://pubmed.ncbi.nlm.nih.gov/35016880/

	Solvent	mg/mL	mM
Solubility
	DMF	15.0	35.92
	DMSO	56.5	135.29
	Ethanol	31.0	74.23

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 417.63 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

Formulation protocol:

1. Jan CR, Jiann BP, Lu YC, Chang HT, Huang JK. Effect of olvanil (N-vanillyl-cis-9-octadecenoamide) on cytosolic Ca2+ increase in renal tubular cells. Life Sci. 2002 Nov 15;71(26):3081-90. doi: 10.1016/s0024-3205(02)02174-4. PMID: 12408875. 2. Di Marzo V, Bisogno T, Melck D, Ross R, Brockie H, Stevenson L, Pertwee R, De Petrocellis L. Interactions between synthetic vanilloids and the endogenous cannabinoid system. FEBS Lett. 1998 Oct 9;436(3):449-54. doi: 10.1016/s0014-5793(98)01175-2. PMID: 9801167. 3. Erin N, Akman M, Aliyev E, Tanrıöver G, Korcum AF. Olvanil activates sensory nerve fibers, increases T cell response and decreases metastasis of breast carcinoma. Life Sci. 2022 Feb 15;291:120305. doi: 10.1016/j.lfs.2022.120305. Epub 2022 Jan 10. PMID: 35016880. 4. Alsalem M, Millns P, Altarifi A, El-Salem K, Chapman V, Kendall DA. Anti-nociceptive and desensitizing effects of olvanil on capsaicin-induced thermal hyperalgesia in the rat. BMC Pharmacol Toxicol. 2016 Jul 21;17(1):31. doi: 10.1186/s40360-016-0074-9. PMID: 27439609; PMCID: PMC4955132.

In vitro protocol:

In vivo protocol:

1. Erin N, Akman M, Aliyev E, Tanrıöver G, Korcum AF. Olvanil activates sensory nerve fibers, increases T cell response and decreases metastasis of breast carcinoma. Life Sci. 2022 Feb 15;291:120305. doi: 10.1016/j.lfs.2022.120305. Epub 2022 Jan 10. PMID: 35016880. 2. Alsalem M, Millns P, Altarifi A, El-Salem K, Chapman V, Kendall DA. Anti-nociceptive and desensitizing effects of olvanil on capsaicin-induced thermal hyperalgesia in the rat. BMC Pharmacol Toxicol. 2016 Jul 21;17(1):31. doi: 10.1186/s40360-016-0074-9. PMID: 27439609; PMCID: PMC4955132.

1: Hayase T. Interrelated involvement of the endocannabinoid/endovanilloid (TRPV1) systems and epigenetic processes in anxiety- and working memory impairment-related behavioural effects of nicotine as a stressor. Addict Biol. 2024 Jul;29(7):10.1111/adb.13421. doi: 10.1111/adb.13421. PMID: 38963015; PMCID: PMC11222983. 2: Bunsick DA, Matsukubo J, Aldbai R, Baghaie L, Szewczuk MR. Functional Selectivity of Cannabinoid Type 1 G Protein-Coupled Receptor Agonists in Transactivating Glycosylated Receptors on Cancer Cells to Induce Epithelial- Mesenchymal Transition Metastatic Phenotype. Cells. 2024 Mar 8;13(6):480. doi: 10.3390/cells13060480. PMID: 38534324; PMCID: PMC10969603. 3: Diaz-Vidal T, Armenta-Pérez VP, Rosales-Rivera LC, Basulto-Padilla GC, Martínez-Pérez RB, Mateos-Díaz JC, Gutiérrez-Mercado YK, Canales-Aguirre AA, Rodríguez JA. Long chain capsaicin analogues synthetized by CALB-CLEAs show cytotoxicity on glioblastoma cell lines. Appl Microbiol Biotechnol. 2024 Dec;108(1):106. doi: 10.1007/s00253-023-12856-y. Epub 2024 Jan 12. PMID: 38217255; PMCID: PMC10786984. 4: Marzęda P, Wróblewska-Łuczka P, Florek-Łuszczki M, Drozd M, Góralczyk A, Łuszczki JJ. Comparison of the Anticancer Effects of Arvanil and Olvanil When Combined with Cisplatin and Mitoxantrone in Various Melanoma Cell Lines-An Isobolographic Analysis. Int J Mol Sci. 2022 Nov 16;23(22):14192. doi: 10.3390/ijms232214192. PMID: 36430670; PMCID: PMC9694208. 5: Lim SG, Seo SE, Jo S, Kim KH, Kim L, Kwon OS. Highly Efficient Real-Time TRPV1 Screening Methodology for Effective Drug Candidates. ACS Omega. 2022 Oct 4;7(41):36441-36447. doi: 10.1021/acsomega.2c04202. PMID: 36278091; PMCID: PMC9583638. 6: Erin N, Akman M, Aliyev E, Tanrıöver G, Korcum AF. Olvanil activates sensory nerve fibers, increases T cell response and decreases metastasis of breast carcinoma. Life Sci. 2022 Feb 15;291:120305. doi: 10.1016/j.lfs.2022.120305. Epub 2022 Jan 10. PMID: 35016880. 7: Alsalem M, Aldossary SA, Haddad M, Altarifi A, Kalbouneh H, Azab B, Mustafa AG, Jaffal SM, El-Salem K. The desensitization of the transient receptor potential vanilloid 1 by nonpungent agonists and its resensitization by bradykinin. Neuroreport. 2020 Aug 5;31(11):781-786. doi: 10.1097/WNR.0000000000001485. PMID: 32618816. 8: Nkambeu B, Salem JB, Beaudry F. Capsaicin and Its Analogues Impede Nocifensive Response of Caenorhabditis elegans to Noxious Heat. Neurochem Res. 2020 Aug;45(8):1851-1859. doi: 10.1007/s11064-020-03049-4. Epub 2020 May 16. PMID: 32418082. 9: Diaz-Vidal T, Armenta-Perez VP, Rosales-Rivera LC, Mateos-Díaz JC, Rodríguez JA. Cross-linked enzyme aggregates of recombinant Candida antarctica lipase B for the efficient synthesis of olvanil, a nonpungent capsaicin analogue. Biotechnol Prog. 2019 Jul;35(4):e2807. doi: 10.1002/btpr.2807. Epub 2019 Mar 29. PMID: 30883025. 10: Tutka P, Wlaź A, Florek-Łuszczki M, Kołodziejczyk P, Bartusik-Aebisher D, Łuszczki JJ. Arvanil, olvanil, AM 1172 and LY 2183240 (various cannabinoid CB1 receptor agonists) increase the threshold for maximal electroshock-induced seizures in mice. Pharmacol Rep. 2018 Feb;70(1):106-109. doi: 10.1016/j.pharep.2017.08.006. Epub 2017 Aug 24. PMID: 29335158. 11: Alsalem M, Millns P, Altarifi A, El-Salem K, Chapman V, Kendall DA. Anti- nociceptive and desensitizing effects of olvanil on capsaicin-induced thermal hyperalgesia in the rat. BMC Pharmacol Toxicol. 2016 Jul 21;17(1):31. doi: 10.1186/s40360-016-0074-9. PMID: 27439609; PMCID: PMC4955132. 12: Rudd JA, Nalivaiko E, Matsuki N, Wan C, Andrews PL. The involvement of TRPV1 in emesis and anti-emesis. Temperature (Austin). 2015 May 21;2(2):258-76. doi: 10.1080/23328940.2015.1043042. PMID: 27227028; PMCID: PMC4843889. 13: Hurley JD, Akers AT, Friedman JR, Nolan NA, Brown KC, Dasgupta P. Non- pungent long chain capsaicin-analogs arvanil and olvanil display better anti- invasive activity than capsaicin in human small cell lung cancers. Cell Adh Migr. 2017 Jan 2;11(1):80-97. doi: 10.1080/19336918.2016.1187368. Epub 2016 May 19. PMID: 27196129; PMCID: PMC5308228. 14: Kaiser M, Chalapala S, Gorzelanny C, Perali RS, Goycoolea FM. The Effect of Capsaicin Derivatives on Tight-Junction Integrity and Permeability of Madin- Darby Canine Kidney Cells. J Pharm Sci. 2016 Feb;105(2):630-638. doi: 10.1016/j.xphs.2015.10.017. Epub 2016 Jan 6. PMID: 26869424. 15: Takao K, Noguchi K, Hashimoto Y, Shirahata A, Sugita Y. Synthesis and evaluation of fatty acid amides on the N-oleoylethanolamide-like activation of peroxisome proliferator activated receptor α. Chem Pharm Bull (Tokyo). 2015;63(4):278-85. doi: 10.1248/cpb.c14-00881. PMID: 25832022. 16: Malek N, Mrugala M, Makuch W, Kolosowska N, Przewlocka B, Binkowski M, Czaja M, Morera E, Di Marzo V, Starowicz K. A multi-target approach for pain treatment: dual inhibition of fatty acid amide hydrolase and TRPV1 in a rat model of osteoarthritis. Pain. 2015 May;156(5):890-903. doi: 10.1097/j.pain.0000000000000132. Erratum in: Pain. 2015 Jul;156(7):1370. PMID: 25719612. 17: Del Prete D, Caprioglio D, Appendino G, Minassi A, Schiano-Moriello A, Di Marzo V, De Petrocellis L. Discovery of non-electrophilic capsaicinoid-type TRPA1 ligands. Bioorg Med Chem Lett. 2015 Mar 1;25(5):1009-11. doi: 10.1016/j.bmcl.2015.01.039. Epub 2015 Jan 28. PMID: 25666822. 18: Kobata K, Takemura I, Tago G, Moriya T, Kubota K, Nakatani S, Wada M, Watanabe T. Formation of long-chain N-vanillyl-acylamides from plant oils. Biosci Biotechnol Biochem. 2014;78(7):1242-5. doi: 10.1080/09168451.2014.912118. Epub 2014 May 28. PMID: 25229865. 19: Barrière DA, Mallet C, Blomgren A, Simonsen C, Daulhac L, Libert F, Chapuy E, Etienne M, Högestätt ED, Zygmunt PM, Eschalier A. Fatty acid amide hydrolase- dependent generation of antinociceptive drug metabolites acting on TRPV1 in the brain. PLoS One. 2013 Aug 5;8(8):e70690. doi: 10.1371/journal.pone.0070690. PMID: 23940628; PMCID: PMC3734263. 20: Tomohiro D, Mizuta K, Fujita T, Nishikubo Y, Kumamoto E. Inhibition by capsaicin and its related vanilloids of compound action potentials in frog sciatic nerves. Life Sci. 2013 Mar 14;92(6-7):368-78. doi: 10.1016/j.lfs.2013.01.011. Epub 2013 Jan 24. PMID: 23352977.