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{{Short description|Pyridine-2-carboxylic acid; bidentate chelating agent}}
{{chembox
{{chembox
| Verifiedimages = changed
|Verifiedimages = changed
| Watchedfields = changed
|Watchedfields = changed
| verifiedrevid = 464206292
|verifiedrevid = 464206292
| ImageFile1_Ref = {{chemboximage|correct|??}}
|ImageFile1_Ref = {{chemboximage|correct|??}}
| ImageFile1 =Picolinic acid.svg
|ImageFile1 =Picolinic acid.svg
| ImageSize1 =180px
|ImageSize1 =180px
| ImageFile2 =Picolinic-acid-3D-balls.png
|ImageFile2 =
| ImageSize2 =180px
|ImageSize2 =180px
| PIN = Pyridine-2-carboxylic acid
|PIN = Pyridine-2-carboxylic acid
| OtherNames = Picolinic acid
|OtherNames = Picolinic acid
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 993
|ChemSpiderID = 993
| InChI = 1/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
|InChI = 1/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
| InChIKey = SIOXPEMLGUPBBT-UHFFFAOYAC
|InChIKey = SIOXPEMLGUPBBT-UHFFFAOYAC
| ChEMBL_Ref = {{ebicite|correct|EBI}}
|ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 72628
|ChEMBL = 72628
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
|StdInChI = 1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SIOXPEMLGUPBBT-UHFFFAOYSA-N
|StdInChIKey = SIOXPEMLGUPBBT-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
|CASNo_Ref = {{cascite|correct|CAS}}
| CASNo =98-98-6
|CASNo =98-98-6
| UNII_Ref = {{fdacite|correct|FDA}}
|UNII_Ref = {{fdacite|correct|FDA}}
| UNII = QZV2W997JQ
|UNII = QZV2W997JQ
| PubChem =1018
|PubChem =1018
| ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28747
|ChEBI = 28747
| SMILES = c1ccnc(c1)C(=O)O
|SMILES = c1ccnc(c1)C(=O)O
}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| C=6 | H=5 | N=1 | O=2
|C=6 | H=5 | N=1 | O=2
| Appearance =White to tan crystalline solid
|Appearance = White solid
⚫
|MeltingPtC = 136 to 138
| Density =
|Density = 1.526 g/cm³
⚫
| MeltingPtC = 136 to 138
⚫
|Solubility = Slightly soluble (0.41%) in water<ref name="CRC Handbook">{{cite journal|last=Lide|first=DR|title=CRC Handbook of Chemistry and Physics, Internet Version 2005, http://hbcpnetbase.com, CRC Press, Boca Raton, Florida, 2005}}</ref>
| MeltingPt_notes =
⚫
}}
| BoilingPt =
⚫
| Solubility =Slightly Soluble (0.41%) in water <ref name="CRC Handbook">{{cite journal|last=Lide|first=DR|title=CRC Handbook of Chemistry and Physics, Internet Version 2005, http://hbcpnetbase.com, CRC Press, Boca Raton, Florida, 2005. }}</ref>
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
⚫
}}
}}
}}
⚫
'''Picolinic acid''' is an [[organic compound]] with the formula C<sub>5</sub>H<sub>4</sub>N(CO<sub>2</sub>H). It is a derivative of [[pyridine]] with a [[carboxylic acid]] 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-position, respectively. It is a white solid that is soluble in water.


⚫
'''Picolinic acid''' is an [[organic compound]] with the formula {{chem2|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.
In [[organic synthesis|synthetic organic chemistry]], has been used as a substrate in the [[Mitsunobu reaction]] and in the [[Hammick reaction]].<ref>[https://books.google.com/books?id=Oa82AAAAQBAJ&q=picolinic+acid#v=snippet&q=picolinic%20acid&f=false Picolinic Acid] chapter in Philip L. Fuchs. Handbook of Reagents for Organic Synthesis: Catalytic Oxidation Reagents. John Wiley & Sons, Jul 29, 2013 {{ISBN|9781118704820}}</ref>{{rp|495ff}}

==Coordination chemistry==
Picolinic acid is a bidentate [[chelating agent]] of elements such as chromium, zinc, manganese, copper, iron, and molybdenum in the human body.<ref name=Grant>{{cite journal|last=Grant|first=RS|author2=Coggan, SE |author3=Smythe, GA |title=The physiological action of picolinic Acid in the human brain.|journal=International Journal of Tryptophan Research : IJTR|year=2009|volume=2|pages=71–9|pmid=22084583|pmc=3195224|doi=10.4137/ijtr.s2469}}</ref>{{rp|72}} Many of its complexes are charge-neutral and thus [[lipophilic]]. After its role in absorption was discovered, zinc dipicolinate [[dietary supplements]] became popular as they were shown to be an effective means of introducing [[zinc]] into the body.<ref name=Grant />


==Production==
==Production==
On a commercial scale, picolinic acid is produced by [[ammoxidation]] of 2-picoline followed by hydrolysis of the resulting nitrile:
⚫
Picolinic acid is formed from [[2-methylpyridine]] by [[oxidation]], e.g. by means of [[potassium permanganate]] (KMnO<sub>4</sub>).<ref name=Ullmann>{{Ullmann|first1=Shinkichi|last1=Shimizu|first2=Nanao|last2=Watanabe|first3=Toshiaki|last3=Kataoka|first4=Takayuki|last4= Shoji|first5=Nobuyuki|last5=Abe|first6=Sinji|last6=Morishita|first7=Hisao|last7=Ichimura|title=Pyridine and Pyridine Derivatives|year=2007|doi=10.1002/14356007.a22_399}}</ref><ref>Harold Hart (Autor), Leslie E. Craine (Autor), David J. Hart (Autor), Christopher M. Hadad (Autor); Nicole Kindler (Übersetzer): ''Organische Chemie'', 3. Auflage, Wiley-VCH, Weinheim 2007, {{ISBN|978-3-527-31801-8}}, S.&nbsp;494.</ref>
:{{chem2|NC5H4CH3 + 1.5 O2 + NH3 -> NC5H4C\tN + 3 H2O}}

:{{chem2|NC5H4C\tN + 2 H2O -> NC5H4CO2H + NH3}}
⚫
It is also produced by oxidation of picoline with nitric acid.<ref name=Ullmann>{{Ullmann|first1=Shinkichi|last1=Shimizu|first2=Nanao|last2=Watanabe|first3=Toshiaki|last3=Kataoka|first4=Takayuki|last4= Shoji|first5=Nobuyuki|last5=Abe|first6=Sinji|last6=Morishita|first7=Hisao|last7=Ichimura|title=Pyridine and Pyridine Derivatives|year=2007|doi=10.1002/14356007.a22_399}}</ref>
:[[File:Oxidation of 2-picoline.png|350px]]
:[[File:Oxidation of 2-picoline.png|350px]]
In the laboratory, picolinic acid is formed from [[2-methylpyridine]] by [[oxidation]] with [[potassium permanganate]] (KMnO<sub>4</sub>).<ref>{{cite journal |doi=10.15227/orgsyn.020.0079 |title=Picolinic Acid Hydrochloride |journal=Organic Syntheses |date=1940 |volume=20 |page=79|first1=Alvin W.|last1=Singer|first2=S. M. |last2=McElvain }}</ref><ref>{{cite book|author=Harold Hart, Leslie E. Craine, David J. Hart, Christopher M. Hadad; Nicole Kindler|title='Organische Chemie 3. Auflage|publisher=Wiley-VCH|location=Weinheim|year=2007|isbn=978-3-527-31801-8|page=494}}</ref>

==Reactions==
[[File:CSD CIF ZNPICH01.jpg|thumb|left|Structure of Zn(picolinate)<sub>2</sub>(H<sub>2</sub>O)<sub>2</sub>.]]
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.<ref>{{cite journal |doi=10.3891/acta.chem.scand.23-3011 |title=The Crystal Structure of Zinc Picolinate Tetrahydrate, Zn(C<sub>6</sub>H<sub>4</sub>O<sub>2</sub>N)<sub>2</sub>(H<sub>2</sub>O)<sub>4</sub> |date=1969 |last1=Lumme |first1=Paavo |last2=Lundgren |first2=Georg |last3=Mark |first3=Wanda |last4=Lundström |first4=Hans |last5=Borch |first5=Gunner |last6=Craig |first6=J. Cymerman |journal=Acta Chemica Scandinavica |volume=23 |pages=3011–3022 }}</ref><ref>{{cite journal |doi=10.1021/ar5004626 |title=Bidentate, Monoanionic Auxiliary-Directed Functionalization of Carbon–Hydrogen Bonds |date=2015 |last1=Daugulis |first1=Olafs |last2=Roane |first2=James |last3=Tran |first3=Ly Dieu |journal=Accounts of Chemical Research |volume=48 |issue=4 |pages=1053–1064 |pmid=25756616 |pmc=4406856 }}</ref>

It is a substrate in the [[Mitsunobu reaction]]. In the [[Hammick reaction]], picolinic acid reacts with ketones to give pyridine-2-carbonols:<ref>{{cite book |last=Fuchs |first=Philip L. |chapter=Picolinic acid |chapter-url=https://books.google.com/books?id=Cbc2AAAAQBAJ&q=picolinic%20acid |url=https://books.google.com/books?id=Cbc2AAAAQBAJ |title=Catalytic Oxidation Reagents |date=2013-07-29 |page=495ff |publisher=Wiley Inc. |oclc=954583821 |isbn=9781118704844}}</ref>
:{{chem2|NC5H4CO2H + R2C\dO -> NC5H4CR2(OH) + CO2}}


==Biosynthesis==
==Biosynthesis==
Picolinic acid is a [[Catabolism|catabolite]] of the amino acid [[tryptophan]] through the [[kynurenine pathway]].<ref name=Grant /><ref>{{cite journal | last1 = Tan | first1 = L | display-authors = etal | date = December 2012 | title = The kynurenine pathway in neurodegenerative diseases: mechanistic and therapeutic considerations | url = | journal = J Neurol Sci | volume = 323 | issue = 1–2| pages = 1–8 | doi = 10.1016/j.jns.2012.08.005 | pmid = 22939820 }}</ref> Its function is unclear, but it has been implicated in a variety neuroprotective, immunological, and anti-proliferative affects. In addition, it is suggested to assist in the absorption of zinc(II) ions and other [[Valence (chemistry)|divalent or trivalent]] ions through the [[small intestine]].<ref name = Evans1982>{{cite journal |last=Evans |first=Gary |year=1982 |title=The Role of Picolinic Acid in Metal Metabolism |url=http://naldc.nal.usda.gov/download/46436/PDF |journal=Life Chemistry Reports |publisher=Harwood Academic Publishers |volume=1 |issue= |pages=57–67 |doi= |access-date=20 March 2015}}</ref>
Picolinic acid is a [[Catabolism|catabolite]] of the amino acid [[tryptophan]] through the [[kynurenine pathway]].<ref>{{cite journal | last1 = Tan | first1 = L. | display-authors = etal | date = December 2012 | title = The kynurenine pathway in neurodegenerative diseases: mechanistic and therapeutic considerations | journal = J Neurol Sci | volume = 323 | issue = 1–2| pages = 1–8 | doi = 10.1016/j.jns.2012.08.005 | pmid = 22939820 | s2cid = 6061945 }}</ref> 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 [[Valence (chemistry)|divalent or trivalent]] ions through the [[small intestine]].<ref name = Evans1982>{{cite journal |last=Evans |first=Gary |year=1982 |title=The Role of Picolinic Acid in Metal Metabolism |url=http://naldc.nal.usda.gov/download/46436/PDF |journal=Life Chemistry Reports |publisher=Harwood Academic Publishers |volume=1 |pages=57–67 |access-date=20 March 2015 |archive-date=26 January 2016 |archive-url=https://web.archive.org/web/20160126125834/http://naldc.nal.usda.gov/download/46436/PDF |url-status=dead }}</ref>


== Picolinates ==
== Picolinates ==
Salts of picolinic acid (picolinates) include,
Salts of picolinic acid (picolinates) include:
* [[Chromium(III) picolinate]]
* [[Chromium(III) picolinate]]
* [[Zinc picolinate]]
* [[Zinc picolinate]]
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{{Use dmy dates|date=March 2018}}
{{Use dmy dates|date=March 2018}}


[[Category:Pyridines]]
[[Category:2-Pyridyl compounds]]
[[Category:Glycine receptor agonists]]
[[Category:Glycine receptor agonists]]
[[Category:Chelating agents]]
[[Category:Chelating agents]]

Latest revision as of 15:44, 17 October 2024

Picolinic acid
Names
Preferred IUPAC name
Pyridine-2-carboxylic acid
Other names
Picolinic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.472 Edit this at Wikidata
UNII
  • InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9) checkY
    Key: SIOXPEMLGUPBBT-UHFFFAOYSA-N checkY
  • 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
Appearance White 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).
checkY verify (what is checkY☒N ?)

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.

Production

[edit]

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]

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

Reactions

[edit]
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

[edit]

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

[edit]

Salts of picolinic acid (picolinates) include:

See also

[edit]

References

[edit]
  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.

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