Decanoic acid

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For the term capric as it related to music see Capriccio (music)
Decanoic acid
Skeletal formula of decanoic acid
Ball-and-stick model of decanoic acid
Identifiers
CAS number 334-48-5 YesY, 1002-62-6 (sodium salt)
PubChem 2969
ChemSpider 2863 YesY
UNII 4G9EDB6V73 YesY
EC number 206-376-4
DrugBank DB03600
KEGG C01571 YesY
ChEBI CHEBI:30813 YesY
ChEMBL CHEMBL107498 YesY
RTECS number HD9100000
Jmol-3D images Image 1
Properties
Molecular formula C10H20O2
Molar mass 172.26 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)[6]
Boiling point 268.7 °C (515.7 °F; 541.8 K) [5]
Solubility in water 0.015 g/100 mL (20 °C)[5]
Solubility Soluble in alcohol, ether, CHCl3, C6H6, CS2, acetone[2]
log P 4.09[5]
Vapor pressure 4.88·10−5 kPa (25 °C)[2]
0.1 kPa (108 °C)[5]
2.03 kPa (160 °C)[3][1]
Acidity (pKa) 4.9[2]
Thermal conductivity 0.372 W/m·K (solid)
0.141 W/m·K (liquid)[4]
Refractive index (nD) 1.4288 (40 °C)[2]
Viscosity 4.327 cP (50 °C)[5]
2.88 cP (70 °C)[4]
Structure
Crystal structure Monoclinic (−3.15 °C)[7]
Space group P21/c[7]
Lattice constant a = 23.1 Å, b = 4.973 Å, c = 9.716 Å[7]
Lattice constant α = 90°, β = 91.28°, γ = 90°
Thermochemistry
Specific
heat capacity
C
475.59 J/mol·K[1]
Std enthalpy of
formation
ΔfHo298
−713.7 kJ/mol[5]
Std enthalpy of
combustion
ΔcHo298
6079.3 kJ/mol[1]
Hazards
MSDS External MSDS
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)[3]
GHS signal word Warning
GHS hazard statements H315, H319, H335[3]
GHS precautionary statements P261, P305+351+338[3]
EU classification Irritant Xi
R-phrases R36/37/38
S-phrases S24/25, S26, S36/37/39
Main hazards Medium toxicity
Ingestion hazard May be toxic
Inhalation hazard May cause irritation
Skin hazard May be toxic on contact
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 110 °C (230 °F; 383 K) [3]
LD50 10 g/kg (rats, oral)[8]
Related compounds
Related fatty acids Caprylic acid
Lauric acid
Related compounds Decanol
Decanal
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Decanoic acid, or 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 arises from the Latin "capric" which pertains to goats due to their olfactory similarities.[9]

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.[6]

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[edit]

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.

Use[edit]

Manufacturing of esters for artificial fruit flavors and perfumes. Also 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[edit]

Decanoate salts and esters of various drugs 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 or salt include nandrolone, fluphenazine, bromperidol, haloperidol and vanoxerine.

Role for earliest life[edit]

A study published in 2013 outlines how decanoic acid may have primed and protected the earliest life on Earth. The scientists discovered that the four bases in RNA bound more readily to the decanoic acid than did the other seven bases tested. Furthermore, the same bases of RNA that preferentially stuck to the fatty acid also protected bags of decanoic acid from disruptive effects of salty seawater.[12]

References[edit]

  1. ^ a b c d 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. ^ a b c d e CID 2969 from PubChem
  3. ^ a b c d e f Sigma-Aldrich Co., Decanoic acid. Retrieved on 2014-06-15.
  4. ^ a b c 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. ^ a b c d e f Lide, David R. (2009). Handbook of Chemistry and Physics (90 ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0. 
  6. ^ a b "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry 73 (4): 685–744. 2001. doi:10.1351/pac200173040685. 
  7. ^ a b c Bond, Andrew D. (2003). "On the crystal structures and melting point alternation of the n-alkyl carboxylic acids". http://www.rsc.org. Royal Society of Chemistry. Retrieved 2014-06-15. 
  8. ^ a b c "CAPRIC ACID". http://www.chemicalland21.com. AroKor Holdings Inc. 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. ^ John McMurry (2008). Organic Chemistry 7th edition. Thompson - Brooks/Cole.  Page 624
  12. ^ Nucleobases bind to and stabilize aggregates of a prebiotic amphiphile, providing a viable mechanism for the emergence of protocells