3612-78-0

Usage

Uses

Used in Cleaning and Detergency Industry:
Dodecyl pyridine-3-carboxylate is used as a surfactant for its ability to lower the surface tension of water, improving the wetting and spreading properties of cleaning and detergency products.
Used in Pharmaceutical Formulation:
Dodecyl pyridine-3-carboxylate is used as a solubility enhancer in pharmaceuticals, helping to improve the solubility and bioavailability of active ingredients.
Used in Agrochemical Formulation:
In agrochemicals, dodecyl pyridine-3-carboxylate is used as a formulation aid to enhance the solubility and bioavailability of active ingredients, ensuring their effectiveness.
It is important to handle dodecyl pyridine-3-carboxylate with care due to its potential toxicity if ingested or inhaled, and its potential to cause skin and eye irritation 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

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

Relevant academic research and scientific papers

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.

Synthesis, structure and magnetic properties of tetrakis-μ-carboxylato-bis(dodecylnicotinato)dicopper(II) complexes; crystal and molecular structure of the decyl carboxylate derivative

Dodecylnicotinate bis-adducts of binuclear copper carboxylates, of the general formula Cu2(O2CCn-1H2n-1)4(C 5H4NCOOC12H25)2, were synthesized for n = 10, 12, 14, 16, 18 and 20, and their crystal structure, thermal behavior and magnetic properties studied. The molecular structure of the decyl derivative has been determined from single-crystal X-ray diffraction data. The dimer is centrosymmetric with the CuII ions in a square-pyramidal coordination with four O-alkyl O atoms [average d(Cu - O) 1.960 (6) A] in the basal plane and the nicotine N atom at apical positions [d(Cu - N) 2.183 (3) A]. The copper ions, 2.615 (1) A apart, are bridged by four O-alkyl carboxylate groups. Both the n = 20 and n = 18 homologues exhibit lamellar phases, which can be related to the supramolecular arrangement found in the n = 10 derivative. The magnetic behavior of the decyl and octadecyl dimers was studied in the 2-300 K temperature range. They exhibit a strong intramolecular antiferromagnetic interaction (Cu-Cu superexchange coupling constant J = -347 cm-1 for the decyl derivative), which can be attributed to a large overlap of the metal 3d orbitals and the oxygen lone pair orbitals of the linking carboxylate groups.

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.