105955-11-1

Basic information

• Product Name: OLDA
• Synonyms: (9Z)-N-[2-(3,4-DIHYDROXYPHENYL)ETHYL]-9-OCTADECENAMIDE;N-[2-(3,4-DIHYDROXYPHENYL)ETHYL]9Z-OCTADECENAMIDE;OLDA;ODA;N-OLEOYLDOPAMINE;N-Oleoyldopamine (OLDA);(Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]octadec-9-enamide
• CAS NO: 105955-11-1
• Molecular Formula: C₂₆H₄₃NO₃
• Molecular Weight: 417.62
• Product Categories: Vanilloid/TRPV channel
• Mol File: 105955-11-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 619.5 °C at 760 mmHg
• Flash Point: 328.4 °C
• Appearance: white/powder
• Density: 1.004 g/cm³
• Vapor Pressure: 6.13E-16mmHg at 25°C
• Refractive Index: 1.521
• Storage Temp.: −20°C
• Solubility: DMSO: ~20 mg/mL, soluble
• CAS DataBase Reference: OLDA(CAS DataBase Reference)
• NIST Chemistry Reference: OLDA(105955-11-1)
• EPA Substance Registry System: OLDA(105955-11-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 105955-11-1(Hazardous Substances Data)

Usage

Uses

N-Oleoyldopamine is a bioactive lipid found in the mammalian brain that selectively activates the transient receptor potential vanilloid type 1 (TRPV1) channel. It is also a 5-lipoxygenase inhibitor.

Biological Activity

Potent endogenous vanilloid TRPV1 (VR1) receptor agonist (EC 50 = 36 nM at hVR1) with low affinity for rCB 1 receptors (K i = 1.6 μ M). Potently induces VR1-mediated thermal hyperalgesia in rats in vivo .

InChI:InChI=1/C26H43NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-26(30)27-21-20-23-18-19-24(28)25(29)22-23/h9-10,18-19,22,28-29H,2-8,11-17,20-21H2,1H3,(H,27,30)/b10-9-

Upstream product

• 51-61-6 dopamine 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 112-80-1 cis-Octadecenoic acid 
• 62-31-7 dopamine hydrochloride 

Relevant articles and documents

A Convenient Protocol for the Synthesis of Fatty Acid Amides

Several classes of biologically occurring fatty acid amides have been reported from mammalian and plant sources. Many amides conjugated with fatty acids of mammalian origin exhibit specific activation of individual receptors. Their potential as pharmacological tools or as lead compounds towards the development of novel therapeutics is of great interest. Hence, access to such amides by a practical, high-yielding and scalable protocol without affecting the geometry or position of sensitive functionalities is needed. A protocol that meets all these requirements involves activation of the corresponding acid with carbonyl diimidazole (CDI) followed by reaction with the desired amine or its hydrochloride. More than fifty compounds have been prepared in generally high yields.

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.

Inhibition of in vitro prostaglandin and leukotriene biosyntheses by cinnamoyl-β-phenethylamine and N-acyldopamine derivatives

N-trans- and N-cis-Feruloyltyramines were isolated as the inhibitors of in vitro prostaglandin (PG) synthesis from an Indonesian medicinal plant, Ipomoea aquatica (Convolvulaceae). In order to clarify structure activity relationships, cinnamoyl-β-phenethylamines with possible combinations of naturally occurring cinnamic acids and β-phenethylamines were synthesized and tested for their inhibitory activities against PG synthetase and arachidonate 5-lipoxygenase. The compounds containing catechol groups such as N-caffeoyl-β-phenethylamine (CaP) showed higher inhibitory effects on PG synthetase. The catechol group was found to M essential for the inhibition of arachidonate 5-lipoxygenase. The investigation of concentration dependent effects on PG biosynthesis revealed that CaP enhanced PG biosynthesis at a lower concentration range, whereas it inhibited the reaction at a higher concentration. The effects of CaP on each reaction step were investigated with purified PG endoperoxide synthase and microsomal PG synthetase. CaP inhibited the cyclooxygenase reaction, while it enhanced the hydroperoxidase reaction. N-Acyldopamines which contain catechol and lipophylic group were synthesized from dopamine and fatty acids to test their inhibitory effects on arachidonate 5-lipoxygenase. N-Linoleoyldopamine was the most active compound and its IC50 value was 2.3 nM in our assay system, in which an IC50 value of AA 861, a specific inhibitor of 5-lipoxygenase, was 8 nM.