{"id":702,"date":"2011-01-24T16:47:00","date_gmt":"2011-01-24T16:47:00","guid":{"rendered":"https:\/\/psiconautica.org\/wordpress\/?p=702"},"modified":"2022-01-31T11:31:26","modified_gmt":"2022-01-31T11:31:26","slug":"cleavage-of-piperic-acid","status":"publish","type":"post","link":"https:\/\/psiconautica.org\/wordpress\/quimica-avanzada\/cleavage-of-piperic-acid\/","title":{"rendered":"Cleavage of piperic acid"},"content":{"rendered":"

Cleavage of piperic acid by 3base<\/h4>\n

via KMnO4<\/h5>\n

piperic acid –> piperonal
\nKMnO4, alkali, 3\u00b0C
\nbyproducts: piperonylic acid, racem. 2,3-dihydroxy-succinic acid, oxalic acid
\n[18], [03], [24]<\/p>\n

via Br2 and NaOH<\/h5>\n

piperic acid\u00a0 \/\u00a0 Br2 ———> tetrabromopiperic acid\u00a0 \u00a0\/\u00a0 NaOH ———>\u00a0piperonal<\/p>\n

Piperic acid reacts quickly with Br2 in CCl4 without forming of HBr
\nto a compound with the molecular formula C12H10Br4O4 [07, page 877]<\/p>\n

Piperic acid addition occured when bromine was added tetrabromopiperic acid (C12H10Br4O4, mp 160-165\u00b0C) resulted wheN bromine in carbon disulfide was the reagent hot sodium hydroxide converted the tetrabromo acid to piperonal [04]<\/p>\n

nitrosation of piperine<\/h5>\n

We have nitrosated piperine using HN02, NOCl and N2O4. the
\ncompounds identified from the nitrosation of piperine are piperonal [05]<\/p>\n

References<\/h5>\n
[03]
\nanalen der chemie und pharmacie 1874 172: 134-167
\n\u00abuntersuchungen ueber die constitution des piperins und seiner<\/b>
\nspaltproducte piperinsaeure und piperidin – vierte abhandlung\u00bb<\/b>
\nrud fittig, w h mielck<\/h5>\n

[04]
\nleo marion, II. the pepper alkaloides, 1. piperine, p.168,
\nthe alkaloids, chemistry and physiology, volume I,
\nacademic press inc, publishers, new york, 1950<\/p>\n

[05]
\nj agric food chem 1992 40(11): 2211-2215<\/a>
\n\u00abnitrosation of piperine using different nitrosating agents:<\/b>
\ncharacterization and mutagenicity of the products\u00bb<\/b>
\nnarmada r shenoy, ahmed s u choughuley, tulsi k shetty, rathin k bhattacharya
\nabstract<\/b>:<\/b> piperine, an N,N-disubstituted amide possessing a methylenedioxy moiety,
\nis the main pungent principle of pepper, a spice consumed by people throughout the
\nworld. on nitrosation the reaction mixture exhibits mutagenic activity toward salmonella
\ntyphimurium strains. in the present work we have nitrosated piperine using nitrous acid
\n(HN02), nitrosyl chloride (NOCl), and dinitrogen tetraoxide (N2O4). the compounds
\nidentified from the nitrosation of piperine are piperonal (PA), 6-nitropiperonal (NPA),
\n3,4-(methylenedioxy)cinnamaldehyde (MDCA),
\n1- [5-(1,3-benzodioxol-6-nitro-5-yl)-l-oxo-2(E) ,4(E)-pentadienyllpiperidine (MNAP),
\n1- [5-(1,3-benzodioxol-5-yl)-l-oxo-2-nitro-2(E),4(E)-pentadienyl] – piperidine (MNOP),
\n1- [5-(1,3-benzodioxol-6-nitro-5-yl)-l-oxo-2-nitro-2(E),4(E)-pentadienyllpiperidine (DNP),
\nand N-nitrosopiperidine (NPIP). the mutagenicity of the unfractionated nitrosated reaction
\nmixture (UPNM) and compounds NPA, MNAP, MNOP and DNP toward S. typhimurium
\nTA 98 and TA 100 strains was studied. compounds NPA and DNP and the unfractionated
\nreaction mixture were found to be mutagenic toward both the strains.<\/p>\n

[07]
\n\u00ablehrbuch der organischen chemie\u00bb<\/b>, 2.berichtigte auflage 1983
\nrobert t morrison, robert n boyd; verlag chemie, weinheim; ISBN 3-527-25761-6<\/p>\n

[18]
\nanalen der chemie und pharmacie 1869 152: 25-58
\n\u00abuntersuchungen ueber die constitution des piperins und seiner<\/b>
\nspaltproducte piperinsaeure und piperidin – erste abhandlung\u00bb<\/b>
\nrud fittig, w h mielck<\/p>\n

[24]
\nberichte der deutschen chemischen gesellschaft 1890 23: 2372-2377
\n\u00abueber die bildung von traubensaeure durch oxydation ungesaettigter saeuren\u00bb<\/b>
\no doebner<\/p>\n","protected":false},"excerpt":{"rendered":"

Cleavage of piperic acid by 3base via KMnO4 piperic acid –> piperonal KMnO4, alkali, 3\u00b0C byproducts: piperonylic acid, racem. 2,3-dihydroxy-succinic acid, oxalic acid [18], [03], [24] via Br2 and NaOH piperic acid\u00a0 \/\u00a0 Br2 ———> tetrabromopiperic acid\u00a0 \u00a0\/\u00a0 NaOH ———>\u00a0piperonal Piperic acid reacts quickly with Br2 in CCl4 without forming of HBr to a compound […]<\/p>\n","protected":false},"author":1,"featured_media":1615,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[24],"tags":[],"class_list":["post-702","post","type-post","status-publish","format-standard","has-post-thumbnail","category-quimica-avanzada"],"yoast_head":"\nCleavage of piperic acid - Psicon\u00e1utica<\/title>\n<meta name=\"robots\" content=\"noindex, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<meta property=\"og:locale\" content=\"es_ES\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Cleavage of piperic acid - Psicon\u00e1utica\" \/>\n<meta property=\"og:description\" content=\"Cleavage of piperic acid by 3base via KMnO4 piperic acid –> piperonal KMnO4, alkali, 3\u00b0C byproducts: piperonylic acid, racem. 2,3-dihydroxy-succinic acid, oxalic acid [18], [03], [24] via Br2 and NaOH piperic acid\u00a0 \/\u00a0 Br2 ———> tetrabromopiperic acid\u00a0 \u00a0\/\u00a0 NaOH ———>\u00a0piperonal Piperic acid reacts quickly with Br2 in CCl4 without forming of HBr to a compound […]\" \/>\n<meta property=\"og:url\" content=\"https:\/\/psiconautica.org\/wordpress\/quimica-avanzada\/cleavage-of-piperic-acid\/\" \/>\n<meta property=\"og:site_name\" content=\"Psicon\u00e1utica\" \/>\n<meta property=\"article:published_time\" content=\"2011-01-24T16:47:00+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2022-01-31T11:31:26+00:00\" \/>\n<meta name=\"author\" content=\"Ra\u00fal del Pino\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Escrito por\" \/>\n\t<meta name=\"twitter:data1\" content=\"Ra\u00fal del Pino\" \/>\n\t<meta name=\"twitter:label2\" content=\"Tiempo de lectura\" \/>\n\t<meta name=\"twitter:data2\" content=\"2 minutos\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\\\/\\\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\\\/\\\/psiconautica.org\\\/wordpress\\\/quimica-avanzada\\\/cleavage-of-piperic-acid\\\/#article\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/psiconautica.org\\\/wordpress\\\/quimica-avanzada\\\/cleavage-of-piperic-acid\\\/\"},\"author\":{\"name\":\"Ra\u00fal del Pino\",\"@id\":\"https:\\\/\\\/psiconautica.org\\\/wordpress\\\/#\\\/schema\\\/person\\\/3afbb90b66878c42e9d66e8e261f3d29\"},\"headline\":\"Cleavage of piperic acid\",\"datePublished\":\"2011-01-24T16:47:00+00:00\",\"dateModified\":\"2022-01-31T11:31:26+00:00\",\"mainEntityOfPage\":{\"@id\":\"https:\\\/\\\/psiconautica.org\\\/wordpress\\\/quimica-avanzada\\\/cleavage-of-piperic-acid\\\/\"},\"wordCount\":419,\"commentCount\":0,\"image\":{\"@id\":\"https:\\\/\\\/psiconautica.org\\\/wordpress\\\/quimica-avanzada\\\/cleavage-of-piperic-acid\\\/#primaryimage\"},\"thumbnailUrl\":\"https:\\\/\\\/psiconautica.org\\\/wordpress\\\/wp-content\\\/uploads\\\/2011\\\/01\\\/1614x1000-1.jpg\",\"articleSection\":[\"Qu\u00edmica avanzada\"],\"inLanguage\":\"es\",\"potentialAction\":[{\"@type\":\"CommentAction\",\"name\":\"Comment\",\"target\":[\"https:\\\/\\\/psiconautica.org\\\/wordpress\\\/quimica-avanzada\\\/cleavage-of-piperic-acid\\\/#respond\"]}]},{\"@type\":\"WebPage\",\"@id\":\"https:\\\/\\\/psiconautica.org\\\/wordpress\\\/quimica-avanzada\\\/cleavage-of-piperic-acid\\\/\",\"url\":\"https:\\\/\\\/psiconautica.org\\\/wordpress\\\/quimica-avanzada\\\/cleavage-of-piperic-acid\\\/\",\"name\":\"Cleavage of piperic acid - 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