Decanoic acid

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Decanoic acid
Skeletal formula
Ball-and-stick model
Identifiers
CAS number 334-48-5 YesY, 1002-62-6 (sodium salt)
PubChem 2969
ChemSpider 2863 YesY
UNII 4G9EDB6V73 YesY
DrugBank DB03600
KEGG C01571 YesY
ChEBI CHEBI:30813 YesY
ChEMBL CHEMBL107498 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H20O2
Molar mass 172.26 g mol−1
Appearance White crystals with strong smell
Density 0.893 g/cm3
Melting point 31.6 °C (88.9 °F; 304.8 K)[2]
Boiling point 269 °C (516 °F; 542 K)
Solubility in water immiscible
Hazards
MSDS External MSDS
R-phrases R36 R38
S-phrases S24 S25 S26 S36 S37 S39
Main hazards Medium toxicity
May cause respiratory irritation
May be toxic on ingestion
May be toxic on skin contact
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)
 YesY (verify) (what is: YesY/N?)
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.[3]

Capric acid occurs naturally in coconut oil (about 10%) and palm kernel oil (about 4%), otherwise it is uncommon in typical seed oils.[4] It is found in the milk of various mammals and to a lesser extent in other animal fats.[2]

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.[5]

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.[6]

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.[7]

References[edit]

  1. ^ Decanoic acid
  2. ^ a b "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry 73 (4): 685–744. 2001. doi:10.1351/pac200173040685. 
  3. ^ "capri-, capr- +". Retrieved 2012-09-28. 
  4. ^ 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
  5. ^ John McMurry (2008). Organic Chemistry 7th edition. Thompson - Brooks/Cole.  Page 624
  6. ^ Capric Acid
  7. ^ Nucleobases bind to and stabilize aggregates of a prebiotic amphiphile, providing a viable mechanism for the emergence of protocells