136181-87-8

Basic information

• Product Name: PALDA
• Synonyms: N-[2-(3,4-DIHYDROXYPHENYL)ETHYL]HEXADECANAMIDE;PALDA;N-PALMITOYL DOPAMINE
• CAS NO: 136181-87-8
• Molecular Formula: C24H41NO3
• Molecular Weight: 391.59
• Product Categories: Vanilloid/TRPV channel
• Mol File: 136181-87-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 589.5 °C at 760 mmHg
• Flash Point: 310.3 °C
• Appearance: /
• Density: 1.006 g/cm³
• Vapor Pressure: 1.7E-14mmHg at 25°C
• Refractive Index: 1.514
• Storage Temp.: Store at +4°C
• CAS DataBase Reference: PALDA(CAS DataBase Reference)
• NIST Chemistry Reference: PALDA(136181-87-8)
• EPA Substance Registry System: PALDA(136181-87-8)

Safety Data

• Hazardous Substances Data: 136181-87-8(Hazardous Substances Data)

Usage

Description

Several different fatty acyl dopamine analogs, such as N-arachidonoyl dopamine (NADA), N-oleoyl dopamine (ODA) and N-palmitoyl dopamine (PALDA), have been isolated and characterized from bovine brain. Structurally, PALDA is the amide of palmitic acid and dopamine and is therefore a “hybrid” analog which incorporates components of both the anandamide-like and dopamine neurotransmitter pathways. Unlike NADA and ODA, PALDA is nearly inactive as a vanilloid receptor 1 (VR1) ligand and fails to elicit hyperalgesic or nocifensive responses in vivo. However, PALDA exhibits an “entourage” effect at concentrations of 0.1-10 μM by potentiating the VR1-mediated effects of NADA and anandamide.

Uses

PALDA is an endogenous fatty acid dopamide.

Biological Activity

Endogenous fatty acid dopamide that displays 'entourage' effects on endovanilloids NADA and anandamide. Inactive at TRPV1 and CB 1 receptors (at concentrations up to 5 μ M) and does not inhibit AMT or FAAH (IC 50 > 25 μ M). However, potentiates TRPV1-mediated effects of NADA; lowers EC 50 from ~ 90 to ~ 30 nM.

InChI:InChI=1/C24H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-24(28)25-19-18-21-16-17-22(26)23(27)20-21/h16-17,20,26-27H,2-15,18-19H2,1H3,(H,25,28)

Upstream product

• 57-10-3 1-hexadecylcarboxylic acid 
• 708261-28-3 N-(3,4-dimethoxy-β-phenylethyl)hexadecanamide 
• 62-31-7 dopamine hydrochloride 
• 146788-12-7 C₂₁H₄₀O₄ 
• 51-61-6 dopamine 
• 623-65-4 palmitic anhydride 
• 645-31-8 3-hydroxytyramine hydrobromide 

Relevant articles and documents

Newly synthesized dopamine ester derivatives and assessment of their antioxidant, antimicrobial and hemolytic activities

Preparation of dopamine derivatives was carried out as a response to the increasing demand for new lipophilized antioxidants in food, cosmetic and pharmaceutical industries. A large series of dopamine esters (DA-C3 to DA-C18:1) with

Efficient N-acyldopamine synthesis

N-Acyldopamines are endogenous analogs of capsaicin that exhibit cannabinoid-like activities and were identified from brain extracts. Among them, N-arachidonoyldopamine (AADA) and N-oleoyldopamine (ODA) were characterized as transient receptor potential vanilloid type V1 channel (TRPV1) ligands. Recently, it was shown that N-acyldopamines may possess diverse physiological roles in addition to their ligand activities. To study the multiple functions and action mechanisms of endogenous N-acyldopamines, a simple and efficient method of N-acyldopamine synthesis was investigated. The eighteen potentially endogenous N-acyl-dopamines and two deuterated ones, N-palmitoyl dopamine-d5 and N-stearoyl dopamine-d5, were efficiently synthesized without protective groups in CH2Cl2 under optimized conditions using propylphosphoric acid cyclic anhydride (PPACA) as a condensation agent.

Synthesis, DNA binding and antitumor evaluation of styelsamine and cystodytin analogues

A series of N-14 sidechain substituted analogues of styelsamine (pyrido[4,3,2-mn]acridine) and cystodytin (pyrido[4,3,2-mn]acridin-4-one) alkaloids have been prepared and evaluated for their DNA binding affinity and antiproliferative activity towards a pa