Picolinic acid

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Picolinic acid
Picolinic acid.svg
Names
Preferred IUPAC name
Pyridine-2-carboxylic acid
Other names
Picolinic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.472 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9) Yes check.svgY
    Key: SIOXPEMLGUPBBT-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
    Key: SIOXPEMLGUPBBT-UHFFFAOYAC
  • c1ccnc(c1)C(=O)O
Properties
C6H5NO2
Molar mass 123.111 g·mol−1
AppearanceWhite solid
Density 1.526 g/cm³
Melting point 136 to 138 °C (277 to 280 °F; 409 to 411 K)
Slightly soluble (0.41%) in water [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Picolinic acid is an organic compound with the formula NC5H4CO2H. It is a derivative of pyridine with a carboxylic acid (COOH) substituent at the 2-position. It is an isomer of nicotinic acid and isonicotinic acid, which have the carboxyl side chain at the 3- and 4-positions, respectively. It is a white solid although impure samples can appear tan. The compoundthat is soluble in water.

Contents

Production

On a commercial scale, picolinic acid is produced by ammoxidation of 2-picoline followed by hydrolysis of the resulting nitrile:

NC5H4CH3 + 1.5 O2 + NH3 → NC5H4C≡N + 3 H2O
NC5H4C≡N + 2 H2O → NC5H4CO2H + NH3

It is also produced by oxidation of picoline with nitric acid. [2]

Oxidation of 2-picoline.png

In the laboratory, picolinic acid is formed from 2-methylpyridine by oxidation with potassium permanganate (KMnO4). [3] [4]

Reactions

Structure of Zn(picolinate)2(H2O)2. CSD CIF ZNPICH01.jpg
Structure of Zn(picolinate)2(H2O)2.

Hydrogenation of picolinic acid gives piperidine-2-carboxylic acid, a precursor to the drug Mepivacaine.

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]

NC5H4CO2H + R2C=O → NC5H4CR2(OH) + CO2

Biosynthesis

Picolinic acid is a catabolite of the amino acid tryptophan through the kynurenine pathway. [8] Its function is unclear, but it has been implicated in a variety of neuroprotective, immunological, and anti-proliferative effects. In addition, it is suggested to assist in the absorption of zinc(II) ions and other divalent or trivalent ions through the small intestine. [9]

Picolinates

Salts of picolinic acid (picolinates) include:

See also

Related Research Articles

<span class="mw-page-title-main">Oxide</span> Chemical compound where oxygen atoms are combined with atoms of other elements

An oxide is a chemical compound containing at least one oxygen atom and one other element in its chemical formula. "Oxide" itself is the dianion of oxygen, an O2– ion with oxygen in the oxidation state of −2. Most of the Earth's crust consists of oxides. Even materials considered pure elements often develop an oxide coating. For example, aluminium foil develops a thin skin of Al2O3 that protects the foil from further oxidation.

<span class="mw-page-title-main">Pyridine</span> Heterocyclic aromatic organic compound

Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one methine group (=CH−) replaced by a nitrogen atom (=N−). It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell. Pyridine is colorless, but older or impure samples can appear yellow, due to the formation of extended, unsaturated polymeric chains, which show significant electrical conductivity. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Historically, pyridine was produced from coal tar. As of 2016, it is synthesized on the scale of about 20,000 tons per year worldwide.

<span class="mw-page-title-main">Aldehyde</span> Organic compound containing the functional group R−CH=O

In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure R−CH=O. The functional group itself can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology.

<span class="mw-page-title-main">Acridine</span> Chemical compound

Acridine is an organic compound and a nitrogen heterocycle with the formula C13H9N. Acridines are substituted derivatives of the parent ring. It is a planar molecule that is structurally related to anthracene with one of the central CH groups replaced by nitrogen. Like the related molecules pyridine and quinoline, acridine is mildly basic. It is an almost colorless solid, which crystallizes in needles. There are few commercial applications of acridines; at one time acridine dyes were popular, but they are now relegated to niche applications, such as with acridine orange. The name is a reference to the acrid odour and acrid skin-irritating effect of the compound.

In organic chemistry, an acyl chloride is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.

<span class="mw-page-title-main">Zinc chloride</span> Chemical compound

Zinc chloride is an inorganic chemical compound with the formula ZnCl2·nH2O, with n ranging from 0 to 4.5, forming hydrates. Zinc chloride, anhydrous and its hydrates, are colorless or white crystalline solids, and are highly soluble in water. Five hydrates of zinc chloride are known, as well as four forms of anhydrous zinc chloride.

<span class="mw-page-title-main">Chromium(III) chloride</span> Chemical compound

Chromium(III) chloride (also called chromic chloride) is an inorganic chemical compound with the chemical formula CrCl3. It forms several hydrates with the formula CrCl3·nH2O, among which are hydrates where n can be 5 (chromium(III) chloride pentahydrate CrCl3·5H2O) or 6 (chromium(III) chloride hexahydrate CrCl3·6H2O). The anhydrous compound with the formula CrCl3 are violet crystals, while the most common form of the chromium(III) chloride are the dark green crystals of hexahydrate, CrCl3·6H2O. Chromium chlorides find use as catalysts and as precursors to dyes for wool.

<span class="mw-page-title-main">Chromium trioxide</span> Chemical compound

Chromium trioxide is an inorganic compound with the formula CrO3. It is the acidic anhydride of chromic acid, and is sometimes marketed under the same name. This compound is a dark-purple solid under anhydrous conditions and bright orange when wet. The substance dissolves in water accompanied by hydrolysis. Millions of kilograms are produced annually, mainly for electroplating. Chromium trioxide is a powerful oxidiser, a mutagen, and a carcinogen.

<i>o</i>-Phenylenediamine Chemical compound

o-Phenylenediamine (OPD) is an organic compound with the formula C6H4(NH2)2. This aromatic diamine is an important precursor to many heterocyclic compounds. OPD is a white compound although samples appear darker owing to oxidation by air. It is isomeric with m-phenylenediamine and p-phenylenediamine.

Isonicotinic acid or pyridine-4-carboxylic acid is an organic compound with the formula C5H4N(CO2H). It is a derivative of pyridine with a carboxylic acid substituent at the 4-position. It is an isomer of picolinic acid and nicotinic acid, which have the carboxyl group at the 2- and 3-position respectively compared to the 4-position for isonicotinic acid.

<span class="mw-page-title-main">Vanadium compounds</span>

Vanadium compounds are compounds formed by the element vanadium (V). The chemistry of vanadium is noteworthy for the accessibility of the four adjacent oxidation states 2–5, whereas the chemistry of the other group 5 elements, niobium and tantalum, are somewhat more limited to the +5 oxidation state. In aqueous solution, vanadium forms metal aquo complexes of which the colours are lilac [V(H2O)6]2+, green [V(H2O)6]3+, blue [VO(H2O)5]2+, yellow-orange oxides [VO(H2O)5]3+, the formula for which depends on pH. Vanadium(II) compounds are reducing agents, and vanadium(V) compounds are oxidizing agents. Vanadium(IV) compounds often exist as vanadyl derivatives, which contain the VO2+ center.

<span class="mw-page-title-main">Dithiocarbamate</span> Chemical group (>N–C(=S)–S–)

In organic chemistry, a dithiocarbamate is a functional group with the general formula R2N−C(=S)−S−R and structure >N−C(=S)−S−. It is the analog of a carbamate in which both oxygen atoms are replaced by sulfur atoms.

<span class="mw-page-title-main">Sodium dimethyldithiocarbamate</span> Chemical compound

Sodium dimethyldithiocarbamate is the organosulfur compound with the formula NaS2NN(CH3)2. It is one of the simplest organic dithiocarbamates. It is a white or pale yellow, water soluble solid. The compound is a precursor to fungicides and rubber chemicals.

2-Methylpyridine, or 2-picoline, is the compound described with formula C6H7N. 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.

<span class="mw-page-title-main">3-Methylpyridine</span> Chemical compound

3-Methylpyridine or 3-picoline, is an organic compound with formula 3-CH3C5H4N. It is one of three positional isomers of methylpyridine, whose structures vary according to where the methyl group is attached around the pyridine ring. This colorless liquid is a precursor to pyridine derivatives that have applications in the pharmaceutical and agricultural industries. Like pyridine, 3-methylpyridine is a colorless liquid with a strong odor and is classified as a weak base.

Pyridine-<i>N</i>-oxide Chemical compound

Pyridine-N-oxide is the heterocyclic compound with the formula C5H5NO. This colourless, hygroscopic solid is the product of the oxidation of pyridine. It was originally prepared using peroxyacids as the oxidising agent. The compound is used infrequently as an oxidizing reagent in organic synthesis.

<span class="mw-page-title-main">Ammoxidation</span> Chemical process for producing nitriles from ammonia and oxygen

In organic chemistry, ammoxidation is a process for the production of nitriles using ammonia and oxygen. It is sometimes called the SOHIO process, acknowledging that ammoxidation was developed at Standard Oil of Ohio. The usual substrates are alkenes. Several million tons of acrylonitrile are produced in this way annually:

<span class="mw-page-title-main">Zinc picolinate</span> Chemical compound

Zinc picolinate (or ZnPic) is the zinc coordination complex derived from picolinic acid and zinc(II). It has the formula Zn(NC5H4CO2)2(H2O)2. The complex adopts an octahedral molecular geometry, containing two bidentate picolinate ligands (conjugate base of picolinic acid) and two aquo ligands. Additionally, two water of crystallization are present, thus the compound crystallizes with the formula Zn(NC5H4CO2)2(H2O)2·2H2O. It is a colorless solid.

<span class="mw-page-title-main">Nicotinonitrile</span> Chemical compound

Nicotinonitrile or 3-cyanopyridine is an organic compound with the formula NCC5H4N. The molecule consists of a pyridine ring with a nitrile group attached to the 3-position. A colorless solid, it is produced by ammoxidation of 3-methylpyridine:

<span class="mw-page-title-main">5-Ethyl-2-methylpyridine</span> Chemical compound

5-Ethyl-2-methylpyridine is an organic compound with the formula (C2H5)(CH3)C5H3N. One of several isomeric pyridines with this formula, this derivative is of interest because it is efficiently prepared from simple reagents and it is a convenient precursor to nicotinic acid, a form of vitamin B3. 5-Ethyl-2-methylpyridine is a colorless liquid.

References

  1. Lide, DR. "CRC Handbook of Chemistry and Physics, Internet Version 2005, http://hbcpnetbase.com, CRC Press, Boca Raton, Florida, 2005".{{cite journal}}: Cite journal requires |journal= (help)
  2. Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399. ISBN   978-3527306732.
  3. Singer, Alvin W.; McElvain, S. M. (1940). "Picolinic Acid Hydrochloride". Organic Syntheses. 20: 79. doi:10.15227/orgsyn.020.0079.
  4. Harold Hart, Leslie E. Craine, David J. Hart, Christopher M. Hadad; Nicole Kindler (2007). 'Organische Chemie 3. Auflage. Weinheim: Wiley-VCH. p. 494. ISBN   978-3-527-31801-8.{{cite book}}: CS1 maint: multiple names: authors list (link)
  5. Lumme, Paavo; Lundgren, Georg; Mark, Wanda; Lundström, Hans; Borch, Gunner; Craig, J. Cymerman (1969). "The Crystal Structure of Zinc Picolinate Tetrahydrate, Zn(C6H4O2N)2(H2O)4". Acta Chemica Scandinavica. 23: 3011–3022. doi:10.3891/acta.chem.scand.23-3011.
  6. Daugulis, Olafs; Roane, James; Tran, Ly Dieu (2015). "Bidentate, Monoanionic Auxiliary-Directed Functionalization of Carbon–Hydrogen Bonds". Accounts of Chemical Research. 48 (4): 1053–1064. doi:10.1021/ar5004626. PMC   4406856 . PMID   25756616.
  7. Fuchs, Philip L. (29 July 2013). "Picolinic acid". Catalytic Oxidation Reagents. Wiley Inc. p. 495ff. ISBN   9781118704844. OCLC   954583821.
  8. Tan, L.; et al. (December 2012). "The kynurenine pathway in neurodegenerative diseases: mechanistic and therapeutic considerations". J Neurol Sci. 323 (1–2): 1–8. doi:10.1016/j.jns.2012.08.005. PMID   22939820. S2CID   6061945.
  9. Evans, Gary (1982). "The Role of Picolinic Acid in Metal Metabolism". Life Chemistry Reports. 1. Harwood Academic Publishers: 57–67. Archived from the original on 26 January 2016. Retrieved 20 March 2015.