{"id":47874,"date":"2023-09-07T17:58:19","date_gmt":"2023-09-07T12:13:19","guid":{"rendered":"https:\/\/thechemistrynotes.com\/?p=47874"},"modified":"2023-09-07T17:58:22","modified_gmt":"2023-09-07T12:13:22","slug":"coumarin-synthesis-applications","status":"publish","type":"post","link":"https:\/\/thechemistrynotes.com\/coumarin-synthesis-applications\/","title":{"rendered":"Coumarin: Definition, Synthetic processes, Applications"},"content":{"rendered":"\n<figure class=\"wp-block-image size-large\"><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"536\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Coumarin-synthesis-1024x536.jpg\" alt=\"Coumarin synthesis\" class=\"wp-image-47880\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Coumarin-synthesis-1024x536.jpg 1024w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Coumarin-synthesis-300x157.jpg 300w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Coumarin-synthesis-768x402.jpg 768w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/Coumarin-synthesis.jpg 1205w\" sizes=\"(max-width: 1024px) 100vw, 1024px\" \/><\/figure>\n\n\n\n<p>Coumarin&nbsp;is a naturally occurring substance belonging to the benzopyrone family. It is also known as&nbsp; 1-benzopyran-2-one. Vogel identified the first parent coumarin from tonka bean (Dipteryx odorata) in 1820. The name coumarin is derived from the French word &#8220;Coumarou&#8221; for tonka bean.<\/p>\n\n\n\n<p>A naturally occurring volatile active molecule called coumarin can be discovered in a broad spectrum of plants. Additionally, food plants like strawberries and cherries contain coumarin. Deer tongue, mullein, Ceylon cinnamon, Cassia cinnamon, and various Prunus species of cherry blossom trees are other plants that contain substantial amounts of coumarin.<\/p>\n\n\n\n<p>Simple coumarins, furanocoumarins, pyrano coumarins (linear and angular type), dihydrofurano coumarins, phenyl coumarins, and bicoumarins are the six basic classes of natural coumarins.<\/p>\n\n\n\n<p>It is estimated that around 1300 natural coumarins isolated from plants, fungi, and bacteria are currently known. Coumarins are secondary metabolites that typically perform a protective role in suppressing many biological processes in nature.<\/p>\n\n\n\n<div id=\"ez-toc-container\" class=\"ez-toc-v2_0_65 counter-hierarchy ez-toc-counter ez-toc-custom ez-toc-container-direction\">\n<div class=\"ez-toc-title-container\">\n<p class=\"ez-toc-title \" >Table of Contents<\/p>\n<span class=\"ez-toc-title-toggle\"><a href=\"#\" class=\"ez-toc-pull-right ez-toc-btn ez-toc-btn-xs ez-toc-btn-default ez-toc-toggle\" aria-label=\"Toggle Table of Content\"><span class=\"ez-toc-js-icon-con\"><span class=\"\"><span class=\"eztoc-hide\" style=\"display:none;\">Toggle<\/span><span class=\"ez-toc-icon-toggle-span\"><svg style=\"fill: #0a0a0a;color:#0a0a0a\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" class=\"list-377408\" width=\"20px\" height=\"20px\" viewBox=\"0 0 24 24\" fill=\"none\"><path d=\"M6 6H4v2h2V6zm14 0H8v2h12V6zM4 11h2v2H4v-2zm16 0H8v2h12v-2zM4 16h2v2H4v-2zm16 0H8v2h12v-2z\" fill=\"currentColor\"><\/path><\/svg><svg style=\"fill: #0a0a0a;color:#0a0a0a\" class=\"arrow-unsorted-368013\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" width=\"10px\" height=\"10px\" viewBox=\"0 0 24 24\" version=\"1.2\" baseProfile=\"tiny\"><path d=\"M18.2 9.3l-6.2-6.3-6.2 6.3c-.2.2-.3.4-.3.7s.1.5.3.7c.2.2.4.3.7.3h11c.3 0 .5-.1.7-.3.2-.2.3-.5.3-.7s-.1-.5-.3-.7zM5.8 14.7l6.2 6.3 6.2-6.3c.2-.2.3-.5.3-.7s-.1-.5-.3-.7c-.2-.2-.4-.3-.7-.3h-11c-.3 0-.5.1-.7.3-.2.2-.3.5-.3.7s.1.5.3.7z\"\/><\/svg><\/span><\/span><\/span><\/a><\/span><\/div>\n<nav><ul class='ez-toc-list ez-toc-list-level-1 ' ><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-1\" href=\"https:\/\/thechemistrynotes.com\/coumarin-synthesis-applications\/#coumarin-synthesis\" title=\"Coumarin synthesis\">Coumarin synthesis<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-2\" href=\"https:\/\/thechemistrynotes.com\/coumarin-synthesis-applications\/#methods-of-coumarin-synthesis\" title=\"Methods of Coumarin synthesis\">Methods of Coumarin synthesis<\/a><ul class='ez-toc-list-level-3' ><li class='ez-toc-heading-level-3'><a class=\"ez-toc-link ez-toc-heading-3\" href=\"https:\/\/thechemistrynotes.com\/coumarin-synthesis-applications\/#perkin-reaction\" title=\"Perkin reaction\">Perkin reaction<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-3'><a class=\"ez-toc-link ez-toc-heading-4\" href=\"https:\/\/thechemistrynotes.com\/coumarin-synthesis-applications\/#pechmann-reaction\" title=\"Pechmann reaction\">Pechmann reaction<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-3'><a class=\"ez-toc-link ez-toc-heading-5\" href=\"https:\/\/thechemistrynotes.com\/coumarin-synthesis-applications\/#knoevenagel-reaction\" title=\"Knoevenagel reaction\">Knoevenagel reaction<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-3'><a class=\"ez-toc-link ez-toc-heading-6\" href=\"https:\/\/thechemistrynotes.com\/coumarin-synthesis-applications\/#houben%e2%80%93hoesch\" title=\"Houben\u2013Hoesch\">Houben\u2013Hoesch<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-3'><a class=\"ez-toc-link ez-toc-heading-7\" href=\"https:\/\/thechemistrynotes.com\/coumarin-synthesis-applications\/#wittig-reaction\" title=\"Wittig reaction\">Wittig reaction<\/a><\/li><\/ul><\/li><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-8\" href=\"https:\/\/thechemistrynotes.com\/coumarin-synthesis-applications\/#other-methods-of-coumarin-synthesis\" title=\"Other Methods of Coumarin Synthesis\">Other Methods of Coumarin Synthesis<\/a><ul class='ez-toc-list-level-3' ><li class='ez-toc-heading-level-3'><a class=\"ez-toc-link ez-toc-heading-9\" href=\"https:\/\/thechemistrynotes.com\/coumarin-synthesis-applications\/#kostanecki-robinson\" title=\"Kostanecki-Robinson\">Kostanecki-Robinson<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-3'><a class=\"ez-toc-link ez-toc-heading-10\" href=\"https:\/\/thechemistrynotes.com\/coumarin-synthesis-applications\/#heck-lactonization-reaction\" title=\"Heck-Lactonization reaction\">Heck-Lactonization reaction<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-3'><a class=\"ez-toc-link ez-toc-heading-11\" href=\"https:\/\/thechemistrynotes.com\/coumarin-synthesis-applications\/#coumarin-synthesis-by-intermolecular-hydroarylation-of-alkene\" title=\"Coumarin synthesis by intermolecular hydroarylation&nbsp; of alkene\">Coumarin synthesis by intermolecular hydroarylation&nbsp; of alkene<\/a><\/li><\/ul><\/li><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-12\" href=\"https:\/\/thechemistrynotes.com\/coumarin-synthesis-applications\/#application-of-coumarin\" title=\"Application of Coumarin\">Application of Coumarin<\/a><\/li><li class='ez-toc-page-1 ez-toc-heading-level-2'><a class=\"ez-toc-link ez-toc-heading-13\" href=\"https:\/\/thechemistrynotes.com\/coumarin-synthesis-applications\/#references\" title=\"References\">References<\/a><\/li><\/ul><\/nav><\/div>\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"coumarin-synthesis\"><\/span><strong>Coumarin synthesis<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<p>Perkin described the coumarin synthesis for the first time in 1868. Heating sodium salt of salicylaldehyde with acetic anhydride resulted in the reaction. Further investigation into this procedure resulted in the broad synthesis of cinnamic acid and its analogs, which is\u00a0known as the Perkin reaction. The Perkin process, von Pechmann condensation, Knoevenagel condensation, Baylis-Hillman reaction, Michael addition, Kostanecki reaction, and Heck lactonization reaction are all common one-step procedures for the synthesis of coumarin derivatives.<\/p>\n\n\n\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"methods-of-coumarin-synthesis\"><\/span><strong>Methods of Coumarin synthesis<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<h3 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"perkin-reaction\"><\/span><strong>Perkin reaction<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h3>\n\n\n\n<p>It involves the reaction between salicylaldehyde and acetic anhydride react to generate coumarin.<\/p>\n\n\n\n<h3 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"pechmann-reaction\"><\/span><strong>Pechmann reaction<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h3>\n\n\n\n<p>The Pechmann reaction involves the condensation of different <a href=\"https:\/\/thechemistrynotes.com\/phenol-classification-preparation-properties-reactions-uses\/\">phenols<\/a> with \u03b2-ketoesters in the presence of homogeneous catalysts such as trifluoroacetic acid or Lewis acids (e.g., AlCl3).<\/p>\n\n\n\n<h3 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"knoevenagel-reaction\"><\/span><strong>Knoevenagel reaction<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h3>\n\n\n\n<p>The Knoevenagel reaction includes the condensation of different o-hydroxy aldehydes with active methylene compounds in the presence of a base catalyst.<\/p>\n\n\n<div class=\"wp-block-image\">\n<figure class=\"aligncenter size-large is-resized\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/untitled-1024x653.png\" alt=\"Methods of coumarin synthesis\" class=\"wp-image-47878\" style=\"width:671px;height:428px\" width=\"671\" height=\"428\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/untitled-1024x653.png 1024w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/untitled-300x191.png 300w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/untitled-768x490.png 768w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/untitled-1536x979.png 1536w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/untitled.png 1871w\" sizes=\"(max-width: 671px) 100vw, 671px\" \/><\/figure><\/div>\n\n\n<h3 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"houben%e2%80%93hoesch\"><\/span><strong>Houben\u2013Hoesch<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h3>\n\n\n\n<p>Houben\u2013Hoesch reaction is a condensation reaction. It involves the reaction of \u03b2-keto nitriles and phenol derivatives to form Comarin.<\/p>\n\n\n\n<h3 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"wittig-reaction\"><\/span><strong>Wittig reaction<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h3>\n\n\n\n<p>Coumarin derivatives are generated as a result of the Wittig reaction.&nbsp;&nbsp;This reaction involves the reaction between&nbsp;aromatic aldehydes or ketones&nbsp;with a phosphonate or phosphorous ylide.<\/p>\n\n\n\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"other-methods-of-coumarin-synthesis\"><\/span><strong>Other Methods of Coumarin Synthesis<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<h3 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"kostanecki-robinson\"><\/span><strong>Kostanecki-Robinson<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h3>\n\n\n\n<p>The Kostanecki-Robinson coupling reaction could be used to create coumarin derivatives. The reaction of aliphatic anhydride with aryl ketone with a hydroxyl group substitution generates the desired product as coumarin with good\u00a0yields.<\/p>\n\n\n<div class=\"wp-block-image\">\n<figure class=\"aligncenter size-full\"><img loading=\"lazy\" decoding=\"async\" width=\"922\" height=\"136\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-33.png\" alt=\"\" class=\"wp-image-47875\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-33.png 922w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-33-300x44.png 300w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-33-768x113.png 768w\" sizes=\"(max-width: 922px) 100vw, 922px\" \/><\/figure><\/div>\n\n\n<h3 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"heck-lactonization-reaction\"><\/span><strong>Heck-Lactonization reaction<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h3>\n\n\n\n<p>The Heck-Lactonization reaction can be used to synthesize coumarin analogs using Pd catalysis, and several reaction conditions were explored utilizing aqueous solutions and organic solvents.<\/p>\n\n\n<div class=\"wp-block-image\">\n<figure class=\"aligncenter size-full is-resized\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-34.png\" alt=\"\" class=\"wp-image-47876\" style=\"width:667px;height:146px\" width=\"667\" height=\"146\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-34.png 799w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-34-300x66.png 300w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-34-768x168.png 768w\" sizes=\"(max-width: 667px) 100vw, 667px\" \/><\/figure><\/div>\n\n\n<h3 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"coumarin-synthesis-by-intermolecular-hydroarylation-of-alkene\"><\/span><strong>Coumarin synthesis by intermolecular hydroarylation&nbsp; of alkene<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h3>\n\n\n\n<p>Direct C-H bond alkenylation is another appealing technique for coumarin synthesis, and some successful instances have been established, including Pd-catalyzed arylation of acrylates. Kitamura and colleagues published the first palladium-catalyzed reaction in 2005.<\/p>\n\n\n\n<p>Several phenols were reacted with ethyl cinnamate, ethyl crotonate, and ethyl acrylate to generate the respective compounds in moderate to good yields. Under the reaction circumstances, the oxidative coupling of electron-rich phenols was a competitive reaction, resulting in lower product yields.<\/p>\n\n\n<div class=\"wp-block-image\">\n<figure class=\"aligncenter size-full is-resized\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-35.png\" alt=\"\" class=\"wp-image-47877\" style=\"width:499px;height:96px\" width=\"499\" height=\"96\" srcset=\"https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-35.png 888w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-35-300x58.png 300w, https:\/\/thechemistrynotes.com\/wp-content\/uploads\/2023\/09\/image-35-768x148.png 768w\" sizes=\"(max-width: 499px) 100vw, 499px\" \/><\/figure><\/div>\n\n\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"application-of-coumarin\"><\/span><strong>Application of Coumarin<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<ul>\n<li>Coumarins can also act as selective enzyme inhibitors, interacting with targets in the therapy of disorders including Parkinson&#8217;s and Alzheimer&#8217;s.<\/li>\n\n\n\n<li>Coumarins have a remarkable range of applications in the biomedical sciences, medical research, and many other industries, including perfumery.<\/li>\n\n\n\n<li>These phytochemicals have antibacterial (agasyllin, felamidin, and armillarisin A) and anti-inflammatory (coumarin and esculetin) activities, as well as anticancer, antiviral, antioxidant (Esculetin), and antifungal characteristics.<\/li>\n<\/ul>\n\n\n\n<h2 class=\"wp-block-heading\"><span class=\"ez-toc-section\" id=\"references\"><\/span><strong>References<\/strong><span class=\"ez-toc-section-end\"><\/span><\/h2>\n\n\n\n<ul>\n<li>https:\/\/www.organic-chemistry.org\/synthesis\/heterocycles\/benzo-fused\/coumarins.shtm.<\/li>\n\n\n\n<li>https:\/\/www.ncbi.nlm.nih.gov\/pmc\/articles\/PMC7022947\/.<\/li>\n\n\n\n<li>https:\/\/byjus.com\/chemistry\/coumarin-synthesis\/<\/li>\n\n\n\n<li>https:\/\/www.intechopen.com\/chapters\/84910<\/li>\n<\/ul>\n","protected":false},"excerpt":{"rendered":"<p>Coumarin&nbsp;is a naturally occurring substance belonging to the benzopyrone family. It is also known as&nbsp; 1-benzopyran-2-one. Vogel identified the first parent coumarin from tonka bean (Dipteryx odorata) in 1820. The &#8230; <a title=\"Coumarin: Definition, Synthetic processes, Applications\" class=\"read-more\" href=\"https:\/\/thechemistrynotes.com\/coumarin-synthesis-applications\/\" aria-label=\"Read more about Coumarin: Definition, Synthetic processes, Applications\">Read more<\/a><\/p>\n","protected":false},"author":4,"featured_media":47880,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[21],"tags":[2873,2871,2874,2872],"_links":{"self":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts\/47874"}],"collection":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/users\/4"}],"replies":[{"embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/comments?post=47874"}],"version-history":[{"count":2,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts\/47874\/revisions"}],"predecessor-version":[{"id":47881,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/posts\/47874\/revisions\/47881"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/media\/47880"}],"wp:attachment":[{"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/media?parent=47874"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/categories?post=47874"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/thechemistrynotes.com\/wp-json\/wp\/v2\/tags?post=47874"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}