Chemistry:Tetronic acid: Difference between revisions

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| MagSus = -52.5·10<sup>−6</sup> cm<sup>3</sup>/mol
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It interconverts between keto and enol [[Chemistry:Tautomer|tautomer]]s:<ref>{{Cite journal | doi = 10.1016/j.arabjc.2015.11.004| title = Advancements in tetronic acid chemistry. Part 1: Synthesis and reactions| journal = Arabian Journal of Chemistry| year = 2015| last1 = Abdou| first1 = Moaz M.| last2 = El-Saeed| first2 = Rasha A.| last3 = Abozeid| first3 = Mohamed A.| last4 = Elattar| first4 = Khaled M.| last5 = Zaki| first5 = E.G.| last6 = Barakat| first6 = Y.| last7 = Ibrahim| first7 = V.| last8 = Fathy| first8 = Mahmoud| last9 = Amine| first9 = M.| last10 = Bondock| first10 = Samir| volume = 12| issue = 4| pages = 464–475| doi-access = free}}</ref>
It interconverts between keto and enol [[Chemistry:Tautomer|tautomer]]s:<ref>{{Cite journal | doi = 10.1016/j.arabjc.2015.11.004| title = Advancements in tetronic acid chemistry. Part 1: Synthesis and reactions| journal = Arabian Journal of Chemistry| year = 2015| last1 = Abdou| first1 = Moaz M.| last2 = El-Saeed| first2 = Rasha A.| last3 = Abozeid| first3 = Mohamed A.| last4 = Elattar| first4 = Khaled M.| last5 = Zaki| first5 = E.G.| last6 = Barakat| first6 = Y.| last7 = Ibrahim| first7 = V.| last8 = Fathy| first8 = Mahmoud| last9 = Amine| first9 = M.| last10 = Bondock| first10 = Samir| volume = 12| issue = 4| pages = 464–475| doi-access = free}}</ref>
:[[File:Tetronsäure-Tautomerie.svg|250px]]
:250px


Many [[Chemistry:Natural product|natural product]]s such as [[Chemistry:Ascorbic acid|ascorbic acid]] (vitamin C), [[Chemistry:Penicillic acid|penicillic acid]], [[Chemistry:Pulvinic acid|pulvinic acid]]s, and abyssomicins possess the β-keto-γ-butyrolactone motif of tetronic acid.<ref>{{Cite journal | doi = 10.1055/s-2006-950202| title = Synthetic Strategies towards Naturally Occurring Tetronic Acids| journal = Synthesis| volume = 2006| issue = 19| pages = 3157| year = 2006| last1 = Georgiadis| first1 = Dimitris| last2 = Zografos| first2 = Alexandros}}</ref>
Many [[Chemistry:Natural product|natural product]]s such as [[Chemistry:Ascorbic acid|ascorbic acid]] (vitamin C), [[Chemistry:Penicillic acid|penicillic acid]], [[Chemistry:Pulvinic acid|pulvinic acid]]s, and abyssomicins possess the β-keto-γ-butyrolactone motif of tetronic acid.<ref>{{Cite journal | doi = 10.1055/s-2006-950202| title = Synthetic Strategies towards Naturally Occurring Tetronic Acids| journal = Synthesis| volume = 2006| issue = 19| pages = 3157| year = 2006| last1 = Georgiadis| first1 = Dimitris| last2 = Zografos| first2 = Alexandros}}</ref>


In [[Chemistry:Organic synthesis|organic synthesis]], it is used as a precursor for other substituted and ring-fused [[Chemistry:Furan|furan]]s and [[Chemistry:Butenolide|butenolide]]s.<ref>{{Cite web | url = https://www.alfa.com/en/catalog/A14079 | publisher = Alfa Aesar | title = Tetronic acid}}</ref><ref>{{cite journal | doi = 10.1021/jo00159a029| title = Substituted .gamma.-butyrolactones. Part 31. 2,4(3H,5H)-Furandione: Heteroannulations with aromatic o-amino carbonyl compounds and condensations with some vic-polyones| journal = The Journal of Organic Chemistry| volume = 48| issue = 11| pages = 1914| year = 1983| last1 = Schmidt| first1 = Diane Grob| last2 = Seemuth| first2 = Paul D.| last3 = Zimmer| first3 = Hans}}</ref>  It is also forms the structural core of a class of pesticides, known as tetronic acid insecticides, which includes [[Chemistry:Spirodiclofen|spirodiclofen]] and spiromesifen.
In [[Chemistry:Organic synthesis|organic synthesis]], it is used as a precursor for other substituted and ring-fused [[Chemistry:Furan|furan]]s and [[Chemistry:Butenolide|butenolide]]s.<ref>{{Cite web | url = https://www.alfa.com/en/catalog/A14079 | publisher = Alfa Aesar | title = Tetronic acid}}</ref><ref>{{cite journal | doi = 10.1021/jo00159a029| title = Substituted .gamma.-butyrolactones. Part 31. 2,4(3H,5H)-Furandione: Heteroannulations with aromatic o-amino carbonyl compounds and condensations with some vic-polyones| journal = The Journal of Organic Chemistry| volume = 48| issue = 11| pages = 1914| year = 1983| last1 = Schmidt| first1 = Diane Grob| last2 = Seemuth| first2 = Paul D.| last3 = Zimmer| first3 = Hans}}</ref>  It is also forms the structural core of a class of pesticides, known as tetronic acid insecticides, which includes [[Chemistry:Spirodiclofen|spirodiclofen]] and spiromesifen.<ref name=":0">{{Cite book |last=Jeschke |first=Peter |url=https://onlinelibrary.wiley.com/doi/book/10.1002/9783527699261 |title=Modern Crop Protection Compounds |last2=Witschel |first2=Matthias |last3=Krämer |first3=Wolfgang |last4=Schirmer |first4=Ulrich |date=25 January 2019 |publisher=Wiley‐VCH |isbn=9783527699261 |edition=3rd |pages=1202-1222 |chapter=32.4 Inhibitors of Lipid Synthesis: Acetyl‐CoA Carboxylase Inhibitors.}}</ref>


==See also==
==See also==

Latest revision as of 01:36, 28 May 2025

Tetronic acid
Tetronic-acid-2D-skeletal.svg
Names
Preferred IUPAC name
4-Hydroxyfuran-2(5H)-one
Other names
  • 3H,5H-Furan-2,4-dione
  • 3-Hydroxybutenolide
  • 3-Hydroxy-2-buteno-4-lactone
  • 3-Oxo-γ-butyrolactone
  • Tetrahydrofuran-2,4-dione
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 208-785-3
UNII
Properties
C4H4O3
Molar mass 100.073 g·mol−1
Melting point 141–143 °C (286–289 °F; 414–416 K) (dec.)[1]
−52.5·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

Tetronic acid is a chemical compound, classified as a γ-lactone, with the molecular formula C4H4O3.

It interconverts between keto and enol tautomers:[2]

250px

Many natural products such as ascorbic acid (vitamin C), penicillic acid, pulvinic acids, and abyssomicins possess the β-keto-γ-butyrolactone motif of tetronic acid.[3]

In organic synthesis, it is used as a precursor for other substituted and ring-fused furans and butenolides.[4][5] It is also forms the structural core of a class of pesticides, known as tetronic acid insecticides, which includes spirodiclofen and spiromesifen.[6]

See also

References

  1. ↑ "2,4(3H,5H)-Furandione". Sigma-Aldrich. http://www.sigmaaldrich.com/catalog/product/aldrich/254592?lang=en. 
  2. ↑ Abdou, Moaz M.; El-Saeed, Rasha A.; Abozeid, Mohamed A.; Elattar, Khaled M.; Zaki, E.G.; Barakat, Y.; Ibrahim, V.; Fathy, Mahmoud et al. (2015). "Advancements in tetronic acid chemistry. Part 1: Synthesis and reactions". Arabian Journal of Chemistry 12 (4): 464–475. doi:10.1016/j.arabjc.2015.11.004. 
  3. ↑ Georgiadis, Dimitris; Zografos, Alexandros (2006). "Synthetic Strategies towards Naturally Occurring Tetronic Acids". Synthesis 2006 (19): 3157. doi:10.1055/s-2006-950202. 
  4. ↑ "Tetronic acid". Alfa Aesar. https://www.alfa.com/en/catalog/A14079. 
  5. ↑ Schmidt, Diane Grob; Seemuth, Paul D.; Zimmer, Hans (1983). "Substituted .gamma.-butyrolactones. Part 31. 2,4(3H,5H)-Furandione: Heteroannulations with aromatic o-amino carbonyl compounds and condensations with some vic-polyones". The Journal of Organic Chemistry 48 (11): 1914. doi:10.1021/jo00159a029. 
  6. ↑ Jeschke, Peter; Witschel, Matthias; Krämer, Wolfgang; Schirmer, Ulrich (25 January 2019). "32.4 Inhibitors of Lipid Synthesis: Acetyl‐CoA Carboxylase Inhibitors.". Modern Crop Protection Compounds (3rd ed.). Wiley‐VCH. pp. 1202-1222. ISBN 9783527699261. https://onlinelibrary.wiley.com/doi/book/10.1002/9783527699261. 



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