Acido petroselinico

Acido petroselinico
Acido petroselinico
Acido petroselinico
Nome IUPAC
acido (6Z)ottadecenoico
Abbreviazioni
18:1Δ6c, 18:1n-12
Nomi alternativi
acido cis6-ottadecenoico
Caratteristiche generali
Formula bruta o molecolareC18H34O2
Numero CAS593-39-5
Numero EINECS209-789-8
PubChem5281125
SMILES
CCCCCCCCCCCC=CCCCCC(=O)O
Indicazioni di sicurezza
Modifica dati su Wikidata · Manuale

L'acido petroselinico è un acido grasso lineare con 18 atomi di carbonio e 1 doppio legame, in posizione 6=7 con configurazione cis. Appartiene al gruppo di acidi omega-12.

L'acido petroselinico è un isomero posizionale dell'acido oleico. Esiste anche un isomero con doppio legame in configurazione trans, presente in natura, chiamato acido petroselaidico, 18:1Δ6t.

L'acido petroselinico nei semi delle piante è sintetizzato dalla Δ4-desaturasi che rimuove gli idrogeni dalla posizione 4 del acido palmitico, 16:0. Il risultante 16:1Δ4 viene poi allungato di due atomi di carbonio dalla elongasi.[1]

Presenza

L'acido petroselinico si presenta come gliceride, cioè estere del glicerolo, in oli e grassi vegetali, a concentrazioni relativamente alte (>30%), e animali. Fu isolato (≈78%) per la prima volta dall'olio di semi di prezzemolo-Petroselinum crispum, dal cui nome latino prese il nome, nel 1909.[2] Si trova in alte concentrazioni negli oli di semi di altre umbelliferae: sedano-Apium graveolens (≈65%), coriandolo-Coriandrum sativum (≈79%), aneto-Anethum graveolens (≈80%) finocchio-Foeniculum vulgare (≈65%); di varie arialiaceae: edera-Hedera helix (≈70%) Aralia spinosa (≈60%). In concentrazioni rilevanti può essere individuato anche negli oli di semi di Griseliniaceae e Garryaceae.[3]

La sua presenza negli animali è a concentrazioni molto inferiori e dipende dall'apporto dietetico o dalla presenza dell'enzima Δ6 desaturasi. Tracce di acido petroselinico e del suo isomero trans sono state individuate nel latte e latticini di alcune specie.[4][5][6][7]

Rispetto all'acido oleico, l'acido petroselinico ha un effetto inibitorio più forte sui batteri, un effetto inibitorio inferiore sulla divisione cellulare e una biodegradazione più lenta.[8][9]

Utilizzo

Il doppio legame Δ6 nell'acido petroselinico lo rende un'interessante materia prima rinnovabile per la produzione di acido adipico. Mediante scissione ossidativa del doppio legame può essere suddiviso in acido laurico e acido adipico.[10] Per presunti effetti benefici l'utilizzo di oli di semi ad alto contenuto di acido petroselinico, come l'olio di semi di coriandolo, è stato promosso sia come ingrediente alimentare[11] che come ingrediente cosmetico[12][13][14] con nome INCI: CORIANDRUM SATIVUM SEED OIL

Note

  1. ^ J Harwood e C Scrimgeour, The Lipid Handbook with CD-ROM, Third Edition, CRC Press, 13 marzo 2007, pp. 1–36, ISBN 978-0-8493-9688-5. URL consultato il 20 dicembre 2019.
  2. ^ (DE) E. Vongerichten e A. Köhler, Über Petroselinsäure, eine neue Ölsäure, in Berichte der deutschen chemischen Gesellschaft, vol. 42, n. 2, 1909-04, pp. 1638–1639, DOI:10.1002/cber.19090420232. URL consultato il 20 dicembre 2019.
  3. ^ SOFA - Oli di semi con acido petroselinico [collegamento interrotto], su sofa.mri.bund.de.
  4. ^ (EN) Frédéric Destaillats, Marjorie Guitard e Cristina Cruz-Hernandez, Identification of Δ6-monounsaturated fatty acids in human hair and nail samples by gas-chromatography–mass-spectrometry using ionic-liquid coated capillary column, in Journal of Chromatography A, vol. 1218, n. 52, 2011-12, pp. 9384–9389, DOI:10.1016/j.chroma.2011.10.095. URL consultato il 20 dicembre 2019.
  5. ^ Dietz Precht, Joachim Molkentin e Frédéric Destaillats, Comparative studies on individual isomeric 18∶1 acids in cow, goat, and ewe milk fats by low-temperature high-resolution capillary gas-liquid chromatography, in Lipids, vol. 36, n. 8, 2001-08, pp. 827–832, DOI:10.1007/s11745-001-0791-8. URL consultato il 20 dicembre 2019.
  6. ^ Simone Hauff e Walter Vetter, Quantitation ofcis- andtrans-Monounsaturated Fatty Acids in Dairy Products and Cod Liver Oil by Mass Spectrometry in the Selected Ion Monitoring Mode, in Journal of Agricultural and Food Chemistry, vol. 57, n. 9, 13 maggio 2009, pp. 3423–3430, DOI:10.1021/jf803665u. URL consultato il 20 dicembre 2019.
  7. ^ R.J. Baer, J. Ryali e D.J. Schingoethe, Composition and Properties of Milk and Butter from Cows Fed Fish Oil, in Journal of Dairy Science, vol. 84, n. 2, 2001-02, pp. 345–353, DOI:10.3168/jds.s0022-0302(01)74483-9. URL consultato il 20 dicembre 2019.
  8. ^ Nikolaus Weber, Klaus Vosmann e Ludger Brüuhl, METABOLISM OF DIETARY PETROSELINIC ACID: A DEAD-END METABOLITE OF DESATURATION/CHAIN ELONGATION REACTIONS, in Nutrition Research, vol. 17, n. 1, 1º gennaio 1997, pp. 89–97, DOI:10.1016/S0271-5317(96)00235-7. URL consultato il 20 dicembre 2019.
  9. ^ Human Metabolome Database: Showing metabocard for Petroselinic acid (HMDB0002080), su hmdb.ca. URL consultato il 20 dicembre 2019.
  10. ^ (EN) Lida L. Placek, A review on petroselinic acid and its derivatives, in Journal of the American Oil Chemists' Society, vol. 40, n. 8, 1963-08, pp. 319–329, DOI:10.1007/BF02631548. URL consultato il 20 dicembre 2019.
  11. ^ EFSA Panel on Dietetic Products, Nutrition and Allergies - SCIENTIFIC OPINION Scientific Opinion on the safety of “coriander seed oil” as a Novel Food ingredient (PDF), su mobil.bfr.bund.de.
  12. ^ Harding, Watkinson e Rawlings, Dry skin, moisturization and corneodesmolysis, in International Journal of Cosmetic Science, vol. 22, n. 1, 2000-02, pp. 21–52, DOI:10.1046/j.1467-2494.2000.00001.x. URL consultato il 20 dicembre 2019.
  13. ^ AV Rawlings, [Plenary Lecture] - Skin active natural products, in Planta Medica, vol. 79, n. 13, 21 agosto 2013, DOI:10.1055/s-0033-1351797. URL consultato il 20 dicembre 2019.
  14. ^ (EN) Petroselinic acid as an anti-irritant in compositions containing alpha-hydroxy acids, 10 settembre 1998. URL consultato il 20 dicembre 2019.

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  Portale Chimica: il portale della scienza della composizione, delle proprietà e delle trasformazioni della materia

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