nicotinate

Nicotinate is the name given to the conjugate base of nicotinic acid (3-pyridinecarboxylic acid) and, more broadly, to salts and esters derived from nicotinic acid in which the carboxyl group is deprotonated or replaced by a cation or organic substituent. The term is commonly used for salts such as sodium nicotinate or calcium nicotinate, which are forms in which the carboxyl group is paired with a metal ion.

Chemically, nicotinate refers to the 3-pyridinecarboxylate anion, a deprotonated form of nicotinic acid that bears the carboxylate group on the pyridine ring. The nicotinate anion retains the aromatic pyridine core and participates in acid-base equilibria in solution; its acidity is governed by the parent nicotinic acid, with pKa values typical of carboxylic acids. In biological contexts, the nicotinate moiety appears in nicotinamide adenine dinucleotide (NAD+) and related cofactors, where it serves as a key electron carrier in redox metabolism.

Biological and nutritional context: nicotinic acid is vitamin B3, and its derivatives, including nicotinate salts, provide niacin equivalents important for cellular energy production. The nicotinate component is essential for forming NAD+ and NADP+, which function as coenzymes in numerous redox reactions. Niacin deficiency can lead to pellagra, while supplementation with nicotinate salts is used to address inadequate niacin intake in some diets.

Applications and safety: nicotinate salts are used as dietary supplements and nutritional fortificants. At high doses, niacin-related forms can cause flushing or other adverse effects, largely associated with nicotinic acid activity rather than the nicotinate anion itself. In organic synthesis, nicotinate esters and salts serve as intermediates in various chemical transformations.