58493-49-5

Basic information

• Product Name: OLVANIL
• Synonyms: n-((4-hydroxy-3-methoxyphenyl)methyl)-9-octadecenamide(z)-;OLVANIL;NE-19550;N-VANILLYLOLEAMIDE;N-VANILLYLOLEOYLAMIDE;N-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-9Z-OCTADECENAMIDE;(n-vanillyl)-9-oleamide;N-VANILLYL-9-OCTADECENAMIDE
• CAS NO: 58493-49-5
• Molecular Formula: C₂₆H₄₃NO₃
• Molecular Weight: 417.62
• Product Categories: Vanilloid/TRPV channel
• Mol File: 58493-49-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 36 °C
• Boiling Point: 596.1 °C at 760 mmHg
• Flash Point: 314.3 °C
• Appearance: white to off-white/powder
• Density: 0.982 g/cm³
• Vapor Pressure: 8.33E-15mmHg at 25°C
• Refractive Index: 1.508
• Storage Temp.: −20°C
• Solubility: H2O: <0.2mg/mL
• PKA: 9.76±0.20(Predicted)
• CAS DataBase Reference: OLVANIL(CAS DataBase Reference)
• NIST Chemistry Reference: OLVANIL(58493-49-5)
• EPA Substance Registry System: OLVANIL(58493-49-5)

Safety Data

• WGK Germany: 3
• RTECS: RG2242130
• Hazardous Substances Data: 58493-49-5(Hazardous Substances Data)

Usage

Description

Olvanil is a structural analog of capsaicin, which is the noxious active component of hot peppers of the Capsicum genus. It is the amide of vanillylamine and oleic acid. Olvanil acts as an agonist at the vanilloid receptor, VR1, inducing desensitization analgesia in rat and mouse models of pain. Olvanil has complex interactions with the cannabinoid system, in that it potentiates the agonist activity of endogenous cannabinoids by inhibiting the reuptake of arachidonyl ethanolamide (AEA). Olvanil is a more potent reuptake inhibitor than AM404, which is commonly used for this purpose (50% inhibition of reuptake at 10 μM versus 12% for AM404 at the same dose). Olvanil is also a CB1 agonist, but does not bind to CB2 receptors or inhibit fatty acid amide hydrolase. The overall activity of olvanil in most models is that of an analgesic, but it is unclear how these effects are mediated by VR1, the CB1 receptor, or other components of the endogenous pain sensation system.

Uses

Different sources of media describe the Uses of 58493-49-5 differently. You can refer to the following data:
1. Analgesic.
2. Olvanil is a TRPV1 agonist more potent than capsaicin.

Biological Activity

Potent vanilloid receptor agonist (pEC 50 values are 8.1 and 7.7 at rat and human VR1 receptors respectively). Also blocks anandamide uptake (IC 50 = 9 μ M) and may bind to CB 1 cannabinoid receptors. Antinociceptive following systemic administration. Also available as part of the Vanilloid TRPV1 Receptor Tocriset? .

InChI:InChI=1/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+

Upstream product

• 112-77-6 (Z)-9-octadecenoyl chloride 
• 1196-92-5 Vanillylamin 
• 112-62-9 Methyl oleate 
• 7149-10-2 vanillylamine hydrochloride 
• 112-80-1 cis-Octadecenoic acid 
• 301-02-0 cis-9-octadecenoamide 

Downstream Products

• 118090-13-4 N-((4-(2-bromoethoxy)-3-methoxyphenyl)methyl)-9Z-octadecenamide 
• 150988-85-5 8-((2S,3R)-3-Octyl-oxiranyl)-octanoic acid 4-hydroxy-3-methoxy-benzylamide 

Relevant articles and documents

Synthesis and evaluation of fatty acid amides on the N-oleoylethanolamide-like activation of peroxisome proliferator activated receptor α

A series of fatty acid amides were synthesized and their peroxisome proliferator-activated receptor α (PPAR-α) agonistic activities were evaluated in a normal rat liver cell line, clone 9. The mRNAs of the PPAR-α downstream genes, carnitine-palmitoyltransferase-1 and mitochondrial 3-hydroxy-3-methylglutaryl-CoA synthase, were determined by real-time reverse transcription-polymerase chain reaction (RT-PCR) as PPAR-α agonistic activities. We prepared nine oleic acid amides. Their PPAR-α agonistic activities were, in decreasing order, N-oleoylhistamine (OLHA), N-oleoylglycine, Oleamide, N-oleoyltyramine, N-oleoylsertonin, and Olvanil. The highest activity was found with OLHA. We prepared and evaluated nine N-acylhistamines (N-acyl-HAs). Of these, OLHA, C16:0-HA, and C18:1Δ9-trans-HA showed similar activity. Activity due to the different chain length of the saturated fatty acid peaked at C16:0-HA. The PPAR-α antagonist, GW6471, inhibited the induction of the PPAR-α downstream genes by OLHA and N-oleoylethanolamide (OEA). These data suggest that N-acyl-HAs could be considered new PPAR-α agonists.

Evaluation of endogenous fatty acid amides and their synthetic analogues as potential anti-inflammatory leads

A series of endogenous fatty acid amides and their analogues (1-78) were prepared, and their inhibitory effects on pro-inflammatory mediators (NO, IL-1β, IL-6, and TNF-α) in LPS-activated RAW264.7 cells were evaluated. Their inhibitory activity on the pro-inflammatory chemokine MDC in IFN-γ-activated HaCaT cells was also examined. The results showed that the activity is strongly dependent on the nature of the fatty acid part of the molecules. As expected, the amides derived from enone fatty acids showed significant activity and were more active than those derived from other types of fatty acids. A variation of the amine headgroup also altered bioactivity profile remarkably, possibly by modulating cell permeability. Regarding the amine part of the molecules, N-acyl dopamines exhibited the most potent activity (IC50 ～2 μM). This is the first report of the inhibitory activity of endogenous fatty acid amides and their analogues on the production of nitric oxide, cytokines (IL-1β, IL-6, and TNF-α) and the chemokine MDC. This study suggests that the enone fatty acid-derived amides (such as N-acyl ethanolamines and N-acyl amino acids) and N-acyl dopamines may be potential anti-inflammatory leads.

Lipophilicity of capsaicinoids and capsinoids influences the multiple activation process of rat TRPV1

Analogs of capsaicin, such as capsaicinoids and capsinoids, activate a cation channel, transient receptor potential cation channel vanilloid subfamily 1 (TRPV1), and then increase the intracellular calcium concentration ([Ca2+]i). Th