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Acido chaulmoogrico

Acido chaulmogrico
Acido idnocarpico
Acido idnocarpico
Nome IUPAC
acido 13-ciclopent-2-en-1-il-tridecanoico
Abbreviazioni
18:1cy
Nomi alternativi
acido 2-ciclopentene-1-tridecanoico
Caratteristiche generali
Formula bruta o molecolareC18H32O2
Numero CAS502-30-7
Numero EINECS249-440-7
PubChem72853
SMILES
C1CC(C=C1)CCCCCCCCCCCCC(=O)O
Indicazioni di sicurezza
Modifica dati su Wikidata · Manuale

L'acido chaulmogrico è un acido grasso composto da 18 atomi di carbonio di cui 5 formano un anello ciclopentilenico nel terminale opposto al gruppo carbossilico.

Fu isolato per la prima volta nel 1904 da Federico B. Power e Frank H. Gornall.[1] Il nome comune dell'acido deriva dall'olio dei semi delle piante del sud-est asiatico da cui è stato isolato, l'olio di Chaulmoogra, che viene utilizzato dalla medicina tradizionale asiatica come rimedio contro lebbra e sarcoidosi.[2][3][4]

L'acido si trova, anche in concentrazioni rilevanti, negli oli di semi di varie specie della famiglia delle Achariaceae e Salicaceae: Oncoba echinata e Caloncoba welwitschii (≈75%) , Hydnocarpus anthelminticus (≈70%), Hydnocarpus heterophylla (≈38%), Hydnocarpus wightiana dal 27% al 38%; e altri in percentuali più basse.[5][6]

L'acido chaulmogrico eserciterebbe una spiccata azione antibatterica, in particolare verso i mycobacteria.[7][8]

L'acido chaulmoogrico come altri acidi grassi ciclopentilenici, in natura,verrebbe sintetizzato tramite elongazione dell'acido aleprolico, biosintetizzato dalla ciclopentenilglicina.[9]

A temperatura ambiente è un solido il cui punto di fusione è 68,5 °C. L'isomero naturale o stereoisomero è destrorotatorio ( + 62,1°)[10][11]mentre l'acido chaulmogrico di sintesi è un racemo.

Note

  1. ^ (EN) Frederick Belding Power e Frank Howorth Gornall, LXXXV.—The constituents of chaulmoogra seeds, in J. Chem. Soc., Trans., vol. 85, n. 0, 1904, pp. 838–851, DOI:10.1039/CT9048500838. URL consultato l'8 gennaio 2020.
  2. ^ (EN) Frederick Belding Power e Marmaduke Barrowcliff, XCI.—The constituents of the seeds of Hydnocarpus Wightiana and of Hydnocarpus anthelmintica. Isolation of a homologue of chaulmoogric acid, in Journal of the Chemical Society, Transactions, vol. 87, n. 0, 1º gennaio 1905, pp. 884–896, DOI:10.1039/CT9058700884. URL consultato il 27 dicembre 2019.
  3. ^ Chaulmoogra Oil, in Hawley's Condensed Chemical Dictionary, John Wiley & Sons, Inc., 15 marzo 2007. URL consultato il 27 dicembre 2019.
  4. ^ Fernando Sergio Dumas dos Santos, Letícia Pumar Alves de Souza e Antonio Carlos Siani, [Chaulmoogra oil as scientific knowledge: the construction of a treatment for leprosy], in Historia, Ciencias, Saude--Manguinhos, vol. 15, n. 1, 2008-01, pp. 29–47, DOI:10.1590/s0104-59702008000100003. URL consultato il 28 dicembre 2019.
  5. ^ SOFA: oli di semi con acidi grassi ciclopentilenici [collegamento interrotto], su sofa.mri.bund.de.
  6. ^ Howard Irving. Cole e Humberto T. Cardoso, Analysis of Chaulmoogra Oils. III. Hydnocarpus Wightiana Oil, in Journal of the American Chemical Society, vol. 61, n. 9, 1º settembre 1939, pp. 2351–2353, DOI:10.1021/ja01878a025. URL consultato il 27 dicembre 2019.
  7. ^ (EN) P. L. Jacobsen e L. Levy, Mechanism by Which Hydnocarpic Acid Inhibits Mycobacterial Multiplication, in Antimicrobial Agents and Chemotherapy, vol. 3, n. 3, 1º marzo 1973, pp. 373–379, DOI:10.1128/AAC.3.3.373. URL consultato il 28 dicembre 2019.
  8. ^ P. L. Jacobsen, H. Ng e L. Levy, The susceptibility of Mycobacteria to hydnocarpic acid, in The American Review of Respiratory Disease, vol. 107, n. 6, 1973-06, pp. 1022–1029, DOI:10.1164/arrd.1973.107.6.1022. URL consultato il 28 dicembre 2019.
  9. ^ Rana, Virendra. (2012). Chemical constituents, biosynthesis and therapeutic applications of chaulmoogra oil. (PDF), su researchgate.net.
  10. ^ HOWARD IRVING COLE, CHEMISTRY OF' LEPROSY DRUGS, International Journal of Leprosy, VOL. 1, No.2 (PDF), su ila.ilsl.br.
  11. ^ BK Girdhar, IAL Textbook of Leprosy, Jaypee Brothers Medical Publishers (P) Ltd., 2010, pp. 333–333, ISBN 978-81-8448-852-4. URL consultato l'8 gennaio 2020.

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