3612-78-0

Basic information

• Product Name: dodecyl pyridine-3-carboxylate
• Synonyms: dodecyl pyridine-3-carboxylate
• CAS NO: 3612-78-0
• Molecular Formula: C₁₈H₂₉NO₂
• Molecular Weight: 0
• Mol File: 3612-78-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 382.9°Cat760mmHg
• Flash Point: 185.4°C
• Appearance: /
• Density: 0.964g/cm³
• Vapor Pressure: 4.56E-06mmHg at 25°C
• Refractive Index: 1.488
• CAS DataBase Reference: dodecyl pyridine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: dodecyl pyridine-3-carboxylate(3612-78-0)
• EPA Substance Registry System: dodecyl pyridine-3-carboxylate(3612-78-0)

Safety Data

• Hazardous Substances Data: 3612-78-0(Hazardous Substances Data)

Usage

General Description

Dodecyl pyridine-3-carboxylate is a chemical compound with the formula C19H29NO2. It belongs to the family of pyridine carboxylates and is commonly used as a surfactant in various industrial applications. Its amphiphilic nature makes it an effective ingredient in cleaning and detergency products, where it helps to lower the surface tension of water and improve the wetting and spreading properties of the products. Additionally, dodecyl pyridine-3-carboxylate is also used in the formulation of pharmaceuticals and agrochemicals due to its ability to enhance the solubility and bioavailability of active ingredients. However, it is important to handle this chemical with care as it can be toxic if ingested or inhaled, and may cause irritation to the skin and eyes upon contact.

InChI:InChI=1/C18H29NO2/c1-2-3-4-5-6-7-8-9-10-11-15-21-18(20)17-13-12-14-19-16-17/h12-14,16H,2-11,15H2,1H3

Synthetic route

nicotinic acid (59-67-6) + 1-dodecylbromide (143-15-7) → n-dodecyl nicotinate (3612-78-0)

Conditions	Yield
With hydrogenchloride; sodium hydroxide In N,N,N,N,N,N-hexamethylphosphoric triamide	77%

3-pyridinecarbonyl chloride (10400-19-8) + 1-dodecyl alcohol (112-53-8) → n-dodecyl nicotinate (3612-78-0)

Conditions	Yield
In toluene at 79.84℃; for 4h; Acylation;

1-dodecyl alcohol (112-53-8) + pyridine-3-carbonyl chloride hydrochloride (20260-53-1) → n-dodecyl nicotinate (3612-78-0)

Conditions	Yield
With triethylamine In dichloromethane Heating;

nicotinic acid (59-67-6) → n-dodecyl nicotinate (3612-78-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / toluene; dimethylformamide / 4 h / Heating 2: toluene / 4 h / 79.84 °C View Scheme

n-iodooctadecane (629-93-6) + n-dodecyl nicotinate (3612-78-0) → 3-[(dodecyloxy)carbonyl]-1-octadecylpyridinium chloride

Conditions	Yield
Stage #1: n-iodooctadecane; n-dodecyl nicotinate for 0.75h; microwave irradiation; Stage #2: With Sephadex ion exchange In methanol Further stages.;

n-dodecyl nicotinate (3612-78-0) + (E/Z)-1-iodo-9-octadecene (73120-38-4) → 3-[(dodecyloxy)carbonyl]-1-[(E/Z)-9-octadecyl]pyridinium chloride

Conditions	Yield
Stage #1: n-dodecyl nicotinate; (E/Z)-1-iodo-9-octadecene for 0.75h; microwave irradiation; Stage #2: With Sephadex ion exchange In methanol Further stages.;

Upstream product

• 59-67-6 nicotinic acid 
• 143-15-7 1-dodecylbromide 
• 112-53-8 1-dodecyl alcohol 
• 20260-53-1 pyridine-3-carbonyl chloride hydrochloride 
• 10400-19-8 3-pyridinecarbonyl chloride 

Relevant articles and documents

Sunfish amphiphiles: Conceptually new carriers for DNA delivery

A conceptually new class of cationic amphiphiles, Sunfish amphiphiles, designed for the delivery of genes into cells is introduced. Sunfish amphiphiles have two hydrophobic tails, connected at the 4- and the N-position to the cationic pyridinium headgroup. Two extreme morphologies visualised by backfolding and combining of both tails at one site (matching situation) or unfolding of the tails at distinct interaction sites at biological membranes will lead to considerable differences in morphological behaviour. The underlying rationale allows controlled release by using this morphological alteration of the Sunfish/helper-lipid/DNA complex (lipoplex). The often-excellent transfection efficiencies are probably related to these morphological changes. In addition, the Sunfish amphiphiles possess low toxicities, resulting in high cell survival after internalisation. The underlying rationale, design, synthesis and in vitro transfection potential are discussed in detail. Moreover, some physico-chemical characteristics of the Sunfish amphiphiles have been studied. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Composition for percutaneous administration

A composition for percutaneous administration containing a nicotinic ester represented by formula (I) STR1 or an isonicotinic ester represented by formula (II) STR2 wherein R and R' each represents an alkyl group having 5 or more carbon atoms, with or without a specific polar compound. The composition improves percutaneous absorption of an active ingredient.