Acido esanoico

Acido esanoico
modello ad asta e sfera
modello ad asta e sfera
Nome IUPAC
acido esanoico
Nomi alternativi
acido caproico, acido capronico[1]
Caratteristiche generali
Formula bruta o molecolareC6H12O2
Massa molecolare (u)116,16
Aspettoliquido incolore e oleoso
Numero CAS142-62-1
Numero EINECS205-550-7
PubChem8892
SMILES
CCCCCC(=O)O
Proprietà chimico-fisiche
Costante di dissociazione acida (pKa) a 298 K4,9
Temperatura di ebollizione205 °C
Indicazioni di sicurezza
Simboli di rischio chimico
tossicità acuta corrosivo
pericolo
Frasi H302 - 311+331 - 314
Consigli P261 - 280 - 305+351+338 - 310 [2]
Modifica dati su Wikidata · Manuale

L'acido esanoico (conosciuto anche come acido caproico o acido capronico) è un acido grasso saturo con sei atomi di carbonio.

Fonti

Questo acido si trova nel burro come trigliceride e nei grassi del latte, sia esterificato che come acido libero (in quantità molto minori)[3]. Appartenendo alla categoria degli acidi organici, contiene un gruppo carbossilico, e a temperatura ambiente si presenta come un liquido incolore con uno sgradevole odore caprino (da cui il nome)[4].

Rispetto ai suoi omologhi inferiori (propionico e butirrico), la sua solubilità in acqua è leggermente inferiore a causa del crescere della lunghezza della catena alchilica (più idrofoba): esso infatti appartiene alla famiglia degli acidi grassi a catena media (in inglese "Medium Chain Fatty Acids")[5]. I suoi sali con i metalli alcalini (sale sodico o potassico), comunque, sono molto idrosolubili.

È stato isolato come componente volatile nell'aroma di aceto e di papaya. Il suo derivato amminico sul carbonio terminale (acido ε-amminocaproico), è un noto farmaco anti-emorragico (fibrinolitico) conosciuto sotto il brand commerciale di Caprolisin[6].

Note

  1. ^ Capronico, su treccani.it. URL consultato il 28 marzo 2019.
  2. ^ Sigma Aldrich; rev. del 12.05.2014
  3. ^ NCI Thesaurus "Caproic Acid (Code C68330)", su ncit.nci.nih.gov. URL consultato il 14 maggio 2017.
  4. ^ (EN) TOXNET HAS MOVED, su toxnet.nlm.nih.gov. URL consultato il 20 novembre 2021.
  5. ^ Human Metabolome Database: Showing metabocard for Caproic acid (HMDB00535), su hmdb.ca. URL consultato il 14 maggio 2017.
  6. ^ Caprolisin | Scheda Tecnica del Farmaco, in Torrinomedica. URL consultato il 14 maggio 2017.

Bibliografia

  • Qian K et al. (2013) J. Econ. Entomol. 106(2): 979-87.
  • Idstein H et al. (1985) Z. Lebensm Unters Forsch. 180(5): 394-97.
  • Longo, Fauci, Kasper, hauser, Jameson, LoScalzo. Harrison, Principi di Medicina Interna, Ed. 18 (2012).

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