| Revision as of 02:36, 27 February 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit |
Latest revision as of 01:59, 28 January 2022 edit undoBattyBot (talk | contribs)Bots1,936,174 editsm →top: Fixed CS1 errors: extra text: volume and general fixesTag: AWB |
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{{chembox |
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{{chembox |
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| verifiedrevid = 413056395 |
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| ImageFile1 = Piperinsäure.svg |
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| verifiedrevid = 416140319 |
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| IUPACName = <small>5-(3,4-methylenedioxyphenyl)-2,4-pentadienoic acid</small> |
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| ImageFile1 = Piperinsäure.svg |
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| Section1 = {{Chembox Identifiers |
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| PIN = (2''E'',4''E'')-5-(2''H''-1,3-Benzodioxol-5-yl)penta-2,4-dienoic acid |
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| CASNo = 136-72-1 |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite}} |
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| CASNo = 136-72-1 |
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| SMILES = OC(=O)\C=C\C=C\c1ccc2OCOc2c1 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = GFG3FLA9UR |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 37316 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 332122 |
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| EINECS = 226-118-4 |
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| PubChem = 5370536 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 4521337 |
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| SMILES = C1OC2=C(O1)C=C(C=C2)/C=C/C=C/C(=O)O |
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| InChI = 1/C12H10O4/c13-12(14)4-2-1-3-9-5-6-10-11(7-9)16-8-15-10/h1-7H,8H2,(H,13,14)/b3-1+,4-2+ |
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| InChIKey = RHBGITBPARBDPH-ZPUQHVIOBF |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C12H10O4/c13-12(14)4-2-1-3-9-5-6-10-11(7-9)16-8-15-10/h1-7H,8H2,(H,13,14)/b3-1+,4-2+ |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = RHBGITBPARBDPH-ZPUQHVIOSA-N |
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| RTECS = |
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| MeSHName = C017637 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=12|H=10|O=4 |
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| C=12 | H=10 | O=4 |
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| Density = |
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| MeltingPtC = |
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| MeltingPtC = |
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| BoilingPt = ''decomposes'' |
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| BoilingPt = ''decomposes'' |
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| pKa = |
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'''Piperic acid''' is a chemical often obtained by the ]-] of the ] ]<ref>{{cite book | url = http://books.google.com/?id=iyzlMSPp-EMC&pg=PA327 | page = 327 | isbn = 9780470741672 | author = Paul M. Dewick. | year = 2009 | publisher = A John Wiley & Sons | location = Chichester | title = Medicinal natural products : a biosynthetic approach }}</ref> from ]<ref>http://chestofbooks.com/health/aromatherapy/The-Volatile-Oils-Vol1/Heliotropin.html</ref>, followed by ]ification of the corresponding ].<ref>http://www.erowid.org/archive/rhodium/chemistry/3base/piperonal.pepper/degradation.piperine/index.html</ref> Piperic acid is an intermediate in the synthesis of other compounds such as ], and as-such may be used to produce ], ] flavorants and ] as well as other useful compounds. |
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'''Piperic acid''' is a chemical often obtained by the ]-] of the ] ]<ref>{{cite book | url = https://books.google.com/books?id=iyzlMSPp-EMC&pg=PA327 | page = 327 | isbn = 978-0-470-74167-2 | author = Paul M. Dewick. | year = 2009 | publisher = A John Wiley & Sons | location = Chichester | title = Medicinal natural products : a biosynthetic approach }}</ref> from ],<ref>{{cite book | title = The Volatile Oils| volume = 1 | author = E. Gildemeister | url = http://chestofbooks.com/health/aromatherapy/The-Volatile-Oils-Vol1/Heliotropin.html}}</ref> followed by ]ification of the corresponding ]. Piperic acid is an intermediate in the synthesis of other compounds such as ], and as-such may be used to produce ], ] flavorants and ] as well as other useful compounds. |
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==Preparation== |
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==Preparation== |
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'''Piperic acid''' can be prepared from the commercially-available alkaloid ], a cyclic ] containing a ] group, by reacting it with a ] such as ], then acidifying the formed piperate salt with ] or another acid. The ] compound piperidine is given off during the base-hydrolysis of piperine and as-such, safety precautions should be taken. |
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Piperic acid can be prepared from the commercially-available alkaloid ], a cyclic ] containing a ] group, by reacting it with a ] such as ], then acidifying the formed piperate salt with ] or another acid. The ] compound piperidine is given off during the base-hydrolysis of piperine and as-such, safety precautions should be taken. |
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==Reactions== |
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==Reactions== |
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Reaction of piperic acid with strong oxidizers such as ] or ], or a halogen such as ] followed by ] causes the ] of the double-bonds, yielding ] via ]<ref>http://www.freepatentsonline.com/5095128.html, Preparation process for piperonal, US Patent No. 5095128</ref><ref>http://www.erowid.org/archive/rhodium/chemistry/3base/piperonal.pepper/cleavage.piperic_acid/index.html</ref>. Piperonal has many uses in industry and is itself a precursor to a good subsection of other chemicals, including the ]ic ] ] and ], collectively known by the street name ecstasy. |
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Reaction of piperic acid with strong oxidizers such as ] or ], or a halogen such as ] followed by ] causes ] of the double-bonds, yielding ] and ].<ref>{{Cite patent | country = US | title = Preparation process for piperonal | number = 5095128 }}</ref> Piperonal has many uses in industry and is itself a precursor to a good subsection of other chemicals. On reduction with sodium ] piperic acid forms α- and β-], C<sub>12</sub>H<sub>12</sub>O<sub>4</sub>, and the latter can take up two further atoms of hydrogen to produce ]. |
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==See also== |
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==See also== |
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