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β-Aminobutyric acid - Wikipedia
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td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>β-Aminobutyric acid </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Beta-aminobutyric_acid.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fc/Beta-aminobutyric_acid.svg/200px-Beta-aminobutyric_acid.svg.png" decoding="async" width="200" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fc/Beta-aminobutyric_acid.svg/300px-Beta-aminobutyric_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fc/Beta-aminobutyric_acid.svg/400px-Beta-aminobutyric_acid.svg.png 2x" data-file-width="512" data-file-height="253" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">3-Aminobutanoic acid</div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">3-Aminobutyric acid<br />β-Aminobutanoic acid<br />Carbocreatine<br />3-Azaniumylbutanoate<br />3-Methyl-β-alanine<br />β-Methyl-β-alanine</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=541-48-0">541-48-0</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=3775-73-3">3775-73-3</a></span> (<i>R</i>)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=3775-72-2">3775-72-2</a></span> (<i>S</i>)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28O%29CC%28N%29C">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.10469.html">10469</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.007.986">100.007.986</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q3604567#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/10932">10932</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/4282SA5CTS">4282SA5CTS</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID4040975">DTXSID4040975</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q3604567#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C4H9NO2/c1-3(5)2-4(6)7/h3H,2,5H2,1H3,(H,6,7)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: OQEBBZSWEGYTPG-UHFFFAOYSA-N</div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C4H9NO2/c1-3(5)2-4(6)7/h3H,2,5H2,1H3,(H,6,7)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: OQEBBZSWEGYTPG-UHFFFAOYAG</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C(O)CC(N)C</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>4</sub><span title="Hydrogen">H</span><sub>9</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002103121000000000♠"></span>103.121</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>β-Aminobutyric acid</b> (BABA) is an <a href="/wiki/Isomer" title="Isomer">isomer</a> of the <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> <a href="/wiki/Aminobutyric_acid" title="Aminobutyric acid">aminobutyric acid</a> with the chemical formula C<sub>4</sub>H<sub>9</sub>NO<sub>2</sub>. It has two isomers, <a href="/wiki/%CE%91-aminobutyric_acid" class="mw-redirect" title="Α-aminobutyric acid">α-aminobutyric acid</a> and <a href="/wiki/%CE%93-aminobutyric_acid" class="mw-redirect" title="Γ-aminobutyric acid">γ-aminobutyric acid</a> (GABA), a <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> in animals that is also found in plants, where it may play a role in signalling.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> All three are <a href="/wiki/Non-proteinogenic_amino_acid" class="mw-redirect" title="Non-proteinogenic amino acid">non-proteinogenic amino acids</a>, not being found in <a href="/wiki/Protein" title="Protein">proteins</a>. BABA is known for its ability to induce <a href="/wiki/Plant_disease_resistance" title="Plant disease resistance">plant disease resistance</a>, as well as increased resistance to <a href="/wiki/Abiotic" class="mw-redirect" title="Abiotic">abiotic</a> stresses, when applied to plants. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Aminobutyric_acid&action=edit&section=1" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Methods to <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthesise</a> BABA are known from at least 1857. Early methods to produce BABA included from <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> and <a href="/wiki/Crotonic_acid" title="Crotonic acid">crotonic acid</a> under pressure; from the acetoacetic ester <a href="/wiki/Phenylhydrazone" class="mw-redirect" title="Phenylhydrazone">phenylhydrazone</a>; or from <a href="/wiki/Malonic_acid" title="Malonic acid">malonic acid</a>, <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a>, and ammonia. In 1957, Zilkha reported a new simpler method based on adding <a href="/wiki/Amine" title="Amine">amines</a> to crotonic acid and then catalytically <a href="/wiki/Hydrogenolysis" title="Hydrogenolysis">hydrogenolysing</a> the product to produce BABA.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Since 2000, methods to produce only the <i>S</i> <a href="/wiki/Stereoisomer" class="mw-redirect" title="Stereoisomer">stereoisomer</a> of BABA have also been reported.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Plant_disease_resistance">Plant disease resistance</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Aminobutyric_acid&action=edit&section=2" title="Edit section: Plant disease resistance"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>BABA was first found to increase the resistance of plants to disease in 1960, when it was observed that it decreased <a href="/wiki/Late_blight" class="mw-redirect" title="Late blight">late blight</a> of <a href="/wiki/Tomato" title="Tomato">tomato</a>.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Further tests were made in the 1960s, but it was not until the 1990s that interest in the compound was renewed.<sup id="cite_ref-cohen_8-0" class="reference"><a href="#cite_note-cohen-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Since then, it has been shown to be effective in many different <a href="/wiki/Pathosystem" title="Pathosystem">pathosystems</a> under controlled conditions. Both <a href="/wiki/Perennial_plant" class="mw-redirect" title="Perennial plant">perennial</a> and <a href="/wiki/Annual_plant" title="Annual plant">annual plants</a> have been shown to respond, as well as both <a href="/wiki/Monocot" class="mw-redirect" title="Monocot">monocot</a> and <a href="/wiki/Dicot" class="mw-redirect" title="Dicot">dicot</a> plants in the <a href="/wiki/Solanaceae" title="Solanaceae">Solanaceae</a>, <a href="/wiki/Cucurbitaceae" title="Cucurbitaceae">Cucurbitaceae</a>, <a href="/wiki/Compositae" class="mw-redirect" title="Compositae">Compositae</a>, <a href="/wiki/Fabaceae" title="Fabaceae">Fabaceae</a>, <a href="/wiki/Brassicaceae" title="Brassicaceae">Brassicaceae</a>, <a href="/wiki/Graminae" class="mw-redirect" title="Graminae">Graminae</a>, <a href="/wiki/Malvaceae" title="Malvaceae">Malvaceae</a>, <a href="/wiki/Rosaceae" title="Rosaceae">Rosaceae</a>, and <a href="/wiki/Vitaceae" title="Vitaceae">Vitaceae</a> <a href="/wiki/Family_(biology)" title="Family (biology)">families</a>. Pathogen groups that have shown a response include <a href="/wiki/Plant_viruses" class="mw-redirect" title="Plant viruses">viruses</a>, bacteria, <a href="/wiki/Nematode" title="Nematode">nematodes</a>, fungi and <a href="/wiki/Oomycete" title="Oomycete">oomycetes</a>.<sup id="cite_ref-cohen_8-1" class="reference"><a href="#cite_note-cohen-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> It has also been shown to be effective in the field at protecting potato and tomato plants from late blight, grape vines from <i><a href="/wiki/Plasmopara_viticola" title="Plasmopara viticola">Plasmopara viticola</a></i> and melons from <i><a href="/wiki/Monosporascus_cannonballus" title="Monosporascus cannonballus">Monosporascus cannonballus</a></i>.<sup id="cite_ref-cohen_8-2" class="reference"><a href="#cite_note-cohen-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Rather than having a direct effect on <a href="/wiki/Plant_pathogen" class="mw-redirect" title="Plant pathogen">plant pathogens</a>, it activates plant immune systems enabling them to resist infection more effectively. The effects that it has been studied extensively using the <a href="/wiki/Model_plant" class="mw-redirect" title="Model plant">model plant</a> <i><a href="/wiki/Arabidopsis_thaliana" title="Arabidopsis thaliana">Arabidopsis thaliana</a></i>.<sup id="cite_ref-cohen_8-3" class="reference"><a href="#cite_note-cohen-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Mode_of_action">Mode of action</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Aminobutyric_acid&action=edit&section=3" title="Edit section: Mode of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>BABA induces defense responses in plants by both physical and biochemical means. The precise mechanism depends on the plant and pathogen species (the <a href="/wiki/Pathosystem" title="Pathosystem">pathosystem</a>).<sup id="cite_ref-cohen_8-4" class="reference"><a href="#cite_note-cohen-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> It is unknown how BABA interacts with plant tissues to increase disease resistance. It does not directly activate defensive genes in isolation, but in combination with an infection, BABA treated plants respond more quickly and strongly to the pathogen.<sup id="cite_ref-ton_10-0" class="reference"><a href="#cite_note-ton-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>In some pathosystems, enhanced <a href="/wiki/Callose" title="Callose">callose</a> and <a href="/wiki/Lignin" title="Lignin">lignin</a> deposition is seen around the point of infection, which act as a physical barrier preventing disease. <a href="/wiki/Pathogenesis-related_protein" title="Pathogenesis-related protein">Pathogenesis-related proteins</a> (PR proteins) which perform many different functions that help to prevent disease accumulate in some BABA treated plants, regardless of whether they are inoculated with a pathogen or not. If infected however, the level of PR proteins tends to increase further. PR proteins are not the only mechanism of preventing infection however, as soil drenches of BABA that do not induce PR protein production, still confer resistance. This may be due to differences between plant families, as the Solanaceae (potato, tomato, pepper) respond by producing PR proteins without any pathogen present, whereas crucifers (Arabidopsis, cauliflower) require a pathogen to induce PR proteins. In other pathosystems, <a href="/wiki/Phytoalexin" title="Phytoalexin">phytoalexins</a> (anti-microbial compounds) accumulate to higher levels in BABA treated plants when they are infected by pathogens, but not when the pathogen is not present. Foliar sprays of BABA can cause small necrotic spots to form on leaves 1 or 2 days after application. This has been suggested to be due to BABA inducing the <a href="/wiki/Hypersensitive_response" title="Hypersensitive response">hypersensitive response</a> which plants normally use to kill infected cells to limit the spread of infection.<sup id="cite_ref-cohen_8-5" class="reference"><a href="#cite_note-cohen-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>BABA applied as a foliar spray causes the plant hormone <a href="/wiki/Salicylic_acid" title="Salicylic acid">salicylic acid</a> (SA) to accumulate, which is a key hormone in controlling <a href="/wiki/Systemic_acquired_resistance" title="Systemic acquired resistance">systemic acquired resistance</a> (SAR). Genetically modified tobacco plants that are unable to accumulate SA are still protected by BABA against some pathogens, but not others, indicating pathosystem-specific mechanisms by which BABA confers resistance. Arabidopsis unable to produce SA, <a href="/wiki/Jasmonic_acid" title="Jasmonic acid">jasmonic acid</a> or <a href="/wiki/Ethylene" title="Ethylene">ethylene</a> (other hormones involved in defence) were still protected from the oomycete <i><a href="/wiki/Peronospora_parasitica" class="mw-redirect" title="Peronospora parasitica">Peronospora parasitica</a></i> but plants unable to produce SA were susceptible to the bacteria <i><a href="/wiki/Pseudomonas_syringae" title="Pseudomonas syringae">Pseudomonas syringae</a></i>. This variation in the hormones required for BABA to confer resistance makes it differ from other synthetic activators of plant defence, which only operate through the SAR pathway of PR proteins.<sup id="cite_ref-cohen_8-6" class="reference"><a href="#cite_note-cohen-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%CE%92-Aminobutyric_acid&action=edit&section=4" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFBouchéFromm2004" class="citation journal cs1">Bouché, N.; Fromm, H. (2004). 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