Decanoic acid

Decanoic acid, also known as capric acid (C10:0) or decylic 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]

"Capric" redirects here. For the musical term, 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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.005.798
EC Number
  • 206-376-4
KEGG
RTECS number
  • HD9100000
UNII
Properties
C10H20O2
Molar mass 172.268 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]
Std enthalpy of
formation (ΔfH⦵298)
 −713.7 kJ/mol[6]
Std enthalpy of
combustion (ΔcH⦵298)
 6079.3 kJ/mol[1]
Hazards
Main hazards Medium toxicity
Safety data sheet External MSDS
GHS pictograms [3]
GHS Signal word Warning
GHS hazard statements
 H315, H319, H335[3]
P261, P305+351+338[3]
Ingestion hazard May be toxic
Inhalation hazard May cause irritation
Skin hazard May be toxic on contact
NFPA 704 (fire diamond)
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
 Nonanoic acid, Undecanoic 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 YN ?)
Infobox references

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] It also comprises 1.62% of the fats from the fruit of the durian species Durio graveolens.[11]

Two other acids are named after goats: caproic (a C6:0 fatty acid) and caprylic (a C8:0 fatty acid). Along with decanoic acid, these total 15% in goat milk fat.[12]

Production

Decanoic acid can be prepared from oxidation of primary alcohol decanol by using chromium trioxide (CrO3) oxidant under acidic conditions.[13]

Neutralization of decanoic acid or saponification of its triglyceride esters with sodium hydroxide yields sodium decanoate, CH3(CH2)8CO2−Na+. This salt 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 adipose 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.[14] This direct inhibition of excitatory neurotransmission by decanoic acid in the brain contributes to the anticonvulsant effect of the MCT ketogenic diet.[14] Decanoic acid and the AMPA receptor 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 perampanel and the ketogenic diet could be synergistic.[14]

Decanoic acid may be responsible for 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.[15][16] Complex I activity of the electron transport chain is substantially elevated by decanoic acid treatment.[15]

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.[17] Whether the ketones β-hydroxybutryate and acetone have direct antiseizure activity is unclear.[14][18][19][20]

gollark: Bad idea. You're buying parts very sloooooowly. There will be new ones out in the future.
gollark: Which numbers?
gollark: I hope 3000-series Ryzens and Navi are good.
gollark: I wonder if it's any good.
gollark: You know, the Vega 56 is about the same price, actually.

See also

References
  1. n-Decanoic acid in Linstrom, Peter J.; Mallard, William 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. CID 2969 from PubChem
  3. Sigma-Aldrich Co., Decanoic acid. Retrieved on 2014-06-15.
  4. Mezaki, Reiji; Mochizuki, Masafumi; Ogawa, Kohei (2000). Engineering Data on Mixing (1st ed.). Elsevier Science B.V. p. 278. ISBN 978-0-444-82802-6.
  5. Beare-Rogers, J. L.; Dieffenbacher, A.; Holm, J. V. (1 January 2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry. 73 (4): 685–744. doi:10.1351/pac200173040685.
  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. D. Bond, Andrew (2004). "On the crystal structures and melting point alternation of the n -alkyl carboxylic acids". New Journal of Chemistry. 28 (1): 104–114. doi:10.1039/B307208H.
  8. "CAPRIC ACID". chemicalland21.com. AroKor Holdings. Retrieved 2014-06-15.
  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. Nasaruddin, Mohd hanif; Noor, Noor Qhairul Izzreen Mohd; Mamat, Hasmadi (2013). "Komposisi Proksimat dan Komponen Asid Lemak Durian Kuning (Durio graveolens) Sabah" [Proximate and Fatty Acid Composition of Sabah Yellow Durian (Durio graveolens)] (PDF). Sains Malaysiana (in Malay). 42 (9): 1283–1288. ISSN 0126-6039. OCLC 857479186. Retrieved 28 November 2017.
  12. Hilditch, T. P.; Jasperson, H. (1944). "The component acids of milk fats of the goat, ewe and mare". Biochemical Journal. 38 (5): 443–447. doi:10.1042/bj0380443. PMC 1258125. PMID 16747831.
  13. McMurry, John (2008). Organic Chemistry (7th ed.). Thompson - Brooks/Cole. p. 624.
  14. Chang, Pishan; Augustin, Katrin; Boddum, Kim; Williams, Sophie; Sun, Min; Terschak, John A.; Hardege, Jörg D.; Chen, Philip E.; Walker, Matthew C.; Williams, Robin S. B. (February 2016). "Seizure control by decanoic acid through direct AMPA receptor inhibition". Brain. 139 (2): 431–443. doi:10.1093/brain/awv325. PMC 4805082. PMID 26608744.
  15. Hughes, Sean David; Kanabus, Marta; Anderson, Glenn; Hargreaves, Iain P.; Rutherford, Tricia; Donnell, Maura O’; Cross, J. Helen; Rahman, Shamima; Eaton, Simon; Heales, Simon J. R. (May 2014). "The ketogenic diet component decanoic acid increases mitochondrial citrate synthase and complex I activity in neuronal cells". Journal of Neurochemistry. 129 (3): 426–433. doi:10.1111/jnc.12646. PMID 24383952.
  16. Malapaka, Raghu R. V.; Khoo, SokKean; Zhang, Jifeng; Choi, Jang H.; Zhou, X. Edward; Xu, Yong; Gong, Yinhan; Li, Jun; Yong, Eu-Leong; Chalmers, Michael J.; Chang, Lin; Resau, James H.; Griffin, Patrick R.; Chen, Y. Eugene; Xu, H. Eric (2 January 2012). "Identification and Mechanism of 10-Carbon Fatty Acid as Modulating Ligand of Peroxisome Proliferator-activated Receptors". Journal of Biological Chemistry. 287 (1): 183–195. doi:10.1074/jbc.M111.294785. PMC 3249069. PMID 22039047.
  17. Chang, Pishan; Terbach, Nicole; Plant, Nick; Chen, Philip E.; Walker, Matthew C.; Williams, Robin S.B. (June 2013). "Seizure control by ketogenic diet-associated medium chain fatty acids". Neuropharmacology. 69: 105–114. doi:10.1016/j.neuropharm.2012.11.004. PMC 3625124. PMID 23177536.
  18. Viggiano, Andrea; Pilla, Raffaele; Arnold, Patrick; Monda, Marcellino; D׳Agostino, Dominic; Coppola, Giangennaro (August 2015). "Anticonvulsant properties of an oral ketone ester in a pentylenetetrazole-model of seizure". Brain Research. 1618: 50–54. doi:10.1016/j.brainres.2015.05.023. PMID 26026798.
  19. Rho, Jong M.; Anderson, Gail D.; Donevan, Sean D.; White, H. Steve (22 April 2002). "Acetoacetate, Acetone, and Dibenzylamine (a Contaminant in l-(+)-β-Hydroxybutyrate) Exhibit Direct Anticonvulsant Actions in Vivo". Epilepsia. 43 (4): 358–361. doi:10.1046/j.1528-1157.2002.47901.x. PMID 11952765.
  20. Ma, Weiyuan; Berg, Jim; Yellen, Gary (4 April 2007). "Ketogenic Diet Metabolites Reduce Firing in Central Neurons by Opening KATP Channels". The Journal of Neuroscience. 27 (14): 3618–3625. doi:10.1523/JNEUROSCI.0132-07.2007. PMC 6672398. PMID 17409226.
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