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Picolinic acid is a bidentate chelating agent of elements such as chromium, zinc, manganese, copper, iron, and molybdenum in the human body. [5] [6] It is a substrate in the Mitsunobu reaction. In the Hammick reaction, picolinic acid reacts with ketones to give pyridine-2-carbonols: [7] NC 5 H 4 CO 2 H + R 2 C=O → NC 5 H 4 CR 2 (OH) + CO 2
He recognized the acid from β–picoline as Nicotinsäure (nicotinic acid or "niacin"), [12] which Weidel had discovered in 1873. [13] When Weidel decarboxylated the carboxylic acid of each isomer – by dry distilling its calcium salt with calcium oxide – the reaction yielded pyridine, thus showing that picoline was a mixture of three ...
The systematic name of this enzyme class is 2-amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioate carboxy-lyase (2-aminomuconate-semialdehyde-forming). Other names in common use include picolinic acid carboxylase, picolinic acid decarboxylase, alpha-amino-beta-carboxymuconate-epsilon-semialdehade decarboxylase, alpha-amino-beta-carboxymuconate-epsilon-semialdehyde, beta-decarboxylase, 2-amino-3-(3 ...
2-Methylpyridine, or 2-picoline, is the compound described with formula C 6 H 7 N. 2-Picoline is a colorless liquid that has an unpleasant odor similar to pyridine. It is mainly used to make vinylpyridine and the agrichemical nitrapyrin .
A pyridinecarboxylic acid is any member of a group of organic compounds which are monocarboxylic derivatives of pyridine. Pyridinecarboxylic acid comes in three isomers: Picolinic acid (2-pyridinecarboxylic acid) Nicotinic acid (3-pyridinecarboxylic acid), also known as Niacin; Isonicotinic acid (4-pyridinecarboxylic acid)
Evidence that the Cr 3+ center coordinates to the pyridine nitrogen comes from a shift in the IR spectra of a C=N vibration at 1602.4 cm −1 for free picolinic acid to 1565.9 cm −1 for chromium(III) picolinate. [11] The bond length between Cr 3+ and the nitrogen atom of the pyridine ring on picolinate ranges from 2.047 to 2.048 Å. [12]
Zinc picolinate (or ZnPic) is the zinc coordination complex derived from picolinic acid and zinc(II). It has the formula Zn(NC 5 H 4 CO 2) 2 (H 2 O) 2.The complex adopts an octahedral molecular geometry, containing two bidentate picolinate ligands (conjugate base of picolinic acid) and two aquo ligands.
Upon heating α-picolinic acid will spontaneously decarboxylate forming the so-called 'Hammick Intermediate' (3).This was initially thought to be an aromatic ylide, but is now believed to be a carbene [5] [6] In the presence of a strong electrophile, such as an aldehyde or ketone, this species will undergo nucleophilic attack faster than proton transfer.