Decanoic acid

For the term capric as it related to music see Capriccio (music)
Decanoic acid
Names
IUPAC name
Decanoic acid
Other names
Capric acid,[1] n-Capric acid, n-Decanoic acid, Decylic acid, n-Decylic acid, C10:0 (Lipid numbers)
Identifiers
334-48-5 YesY
1002-62-6 (sodium salt) N
3D model (Jmol) Interactive image
ChEBI CHEBI:30813 YesY
ChEMBL ChEMBL107498 YesY
ChemSpider 2863 YesY
DrugBank DB03600 N
ECHA InfoCard 100.005.798
EC Number 206-376-4
5532
KEGG C01571 YesY
PubChem 2969
RTECS number HD9100000
UNII 4G9EDB6V73 YesY
Properties
C10H20O2
Molar mass 172.27 g·mol−1
Appearance White crystals
Odor Strong rancid and unpleasant[2]
Density 0.893 g/cm3 (25 °C)[3]
0.8884 g/cm3 (35.05 °C)
0.8773 g/cm3 (50.17 °C)[4]
Melting point 31.6 °C (88.9 °F; 304.8 K)[5]
Boiling point 268.7 °C (515.7 °F; 541.8 K) [6]
0.015 g/100 mL (20 °C)[6]
Solubility Soluble in alcohol, ether, CHCl3, C6H6, CS2, acetone[2]
log P 4.09[6]
Vapor pressure 4.88·10−5 kPa (25 °C)[2]
0.1 kPa (108 °C)[6]
2.03 kPa (160 °C)[1][3]
Acidity (pKa) 4.9[2]
Thermal conductivity 0.372 W/m·K (solid)
0.141 W/m·K (liquid)[4]
1.4288 (40 °C)[2]
Viscosity 4.327 cP (50 °C)[6]
2.88 cP (70 °C)[4]
Structure
Monoclinic (−3.15 °C)[7]
P21/c[7]
a = 23.1 Å, b = 4.973 Å, c = 9.716 Å[7]
α = 90°, β = 91.28°, γ = 90°
Thermochemistry
475.59 J/mol·K[1]
−713.7 kJ/mol[6]
6079.3 kJ/mol[1]
Hazards
Main hazards Medium toxicity
Safety data sheet External MSDS
GHS pictograms [3]
GHS signal word Warning
H315, H319, H335[3]
P261, P305+351+338[3]
Xi
R-phrases R36/37/38
S-phrases S24/25, S26, S36/37/39
Ingestion hazard May be toxic
Inhalation hazard May cause irritation
Skin hazard May be toxic on contact
NFPA 704
Flash point 110 °C (230 °F; 383 K) [3]
Lethal dose or concentration (LD, LC):
10 g/kg (rats, oral)[8]
Related compounds
Related fatty acids
 Caprylic acid
Lauric acid
Related compounds
 Decanol
Decanal
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Decanoic acid (capric acid) is a saturated fatty acid. Its formula is CH3(CH2)8COOH. Salts and esters of decanoic acid are called decanoates or "caprates". The term capric acid is derived from the Latin "caper / capra" (goat) because the sweaty, unpleasant smell of the compound is reminiscent of goats.[9]

Occurrence

Capric acid occurs naturally in coconut oil (about 10%) and palm kernel oil (about 4%), otherwise it is uncommon in typical seed oils.[10] It is found in the milk of various mammals and to a lesser extent in other animal fats.[5]

Two other acids are named after goats: caproic (a C6 fatty acid) and caprylic (a C8 fatty acid). Along with decanoic acid, these total 15% in goat milk fat.

Production

Decanoic acid can be prepared from oxidation of primary alcohol decanol by using chromium trioxide (CrO3) oxidant under acidic conditions.[11]

Neutralization of decanoic acid or saponification of its esters, typically triglycerides, with sodium hydroxide will give sodium decanoate. This salt (CH3(CH2)8COO−Na+) is a component of some types of soap.

Uses

Decanoic acid is used in the manufacture of esters for artificial fruit flavors and perfumes. It is also used as an intermediate in chemical syntheses. It is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals.[8]

Pharmaceuticals

Decanoate ester prodrugs of various pharmaceuticals are available. Since decanoic acid is a fatty acid, forming a salt or ester with a drug will increase its lipophilicity and its affinity for fatty tissue. Since distribution of a drug from fatty tissue is usually slow, one may develop a long-acting injectable form of a drug (called a Depot injection) by using its decanoate form. Some examples of drugs available as a decanoate ester include nandrolone, fluphenazine, bromperidol, and haloperidol.

Effects

Decanoic acid acts as a non-competitive AMPA receptor antagonist at therapeutically relevant concentrations, in a voltage- and subunit-dependent manner, and this is sufficient to explain its antiseizure effects.[12] This direct inhibition of excitatory neurotransmission by decanoic acid in the brain contributes to the anticonvulsant effect of the MCT ketogenic diet.[12] Decanoic acid and the AMPAr antagonist drug perampanel act at separate sites on the AMPA receptor, and so it is possible that they have a cooperative effect at the AMPA receptor, suggesting that permapanel and the ketogenic diet could be synergistic.[12]

Decanoic acid may mimic the mitochondrial proliferation associated with the ketogenic diet, and that this may occur via PPARγ receptor agonism and its target genes involved in mitochondrial biogenesis.[13]

It should however be noted that orally ingested medium chain fatty acids would be very rapidly degraded by first-pass metabolism by being taken up in the liver via the portal vein, and are quickly metabolized via coenzyme A intermediates through β-oxidation and the citric acid cycle to produce carbon dioxide, acetate and ketone bodies.[14] It is unclear whether the ketones β-hydroxybutryate and acetone have direct antiseizure activity.[12][15][16][17]

See also

References

  1. 1 2 3 4 n-Decanoic acid in Linstrom, P.J.; Mallard, W.G. (eds.) NIST Chemistry WebBook, NIST Standard Reference Database Number 69. National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov (retrieved 2014-06-15)
  2. 1 2 3 4 5 CID 2969 from PubChem
  3. 1 2 3 4 5 6 Sigma-Aldrich Co., Decanoic acid. Retrieved on 2014-06-15.
  4. 1 2 3 Mezaki, Reiji; Mochizuki, Masafumi; Ogawa, Kohei (2000). Engineering Data on Mixing (1st ed.). Elsevier Science B.V. p. 278. ISBN 0-444-82802-8.
  5. 1 2 "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry. 73 (4): 685–744. 2001. doi:10.1351/pac200173040685.
  6. 1 2 3 4 5 6 Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
  7. 1 2 3 Bond, Andrew D. (2003). "On the crystal structures and melting point alternation of the n-alkyl carboxylic acids" (PDF). http://www.rsc.org. Royal Society of Chemistry. Retrieved 2014-06-15. External link in |website= (help)
  8. 1 2 3 "CAPRIC ACID". http://www.chemicalland21.com. AroKor Holdings Inc. Retrieved 2014-06-15. External link in |website= (help)
  9. ↑ "capri-, capr- +". Retrieved 2012-09-28.
  10. ↑ David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia of Industrial Chemistry, 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a10_245.pub2
  11. ↑ John McMurry (2008). Organic Chemistry 7th edition. Thompson - Brooks/Cole. Page 624
  12. 1 2 3 4 "Seizure control by decanoic acid through direct AMPA receptor inhibition". 2015-11-25. Retrieved 2015-11-25.
  13. ↑ Hughes SD, Kanabus M, Anderson G, Hargreaves IP, Rutherford T, O'Donnell M, Cross JH, Rahman S, Eaton S, Heales SJ (2014). "The ketogenic diet component decanoic acid increases mitochondrial citrate synthase and complex I activity in neuronal cells". Journal of Neurochemistry. 129 (3): 426–33. doi:10.1111/jnc.12646. PMID 24383952. Retrieved 2015-11-26.
  14. ↑ "Seizure control by ketogenic diet-associated medium chain fatty acids". 2013. Retrieved 2015-11-25.
  15. ↑ "Anticonvulsant properties of an oral ketone ester in a pentylenetetrazole-model of seizure.". Retrieved 2016-01-19.
  16. ↑ "Acetoacetate, acetone, and dibenzylamine (a contaminant in l-(+)-beta-hydroxybutyrate) exhibit direct anticonvulsant actions in vivo.". Retrieved 2016-01-19.
  17. ↑ "Ketogenic diet metabolites reduce firing in central neurons by opening K(ATP) channels.". Retrieved 2016-01-19.
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