Decanoic acid

Decanoic acid
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
CAS number	334-48-5 Y, 1002-62-6 (sodium salt)
PubChem	2969
ChemSpider	2863 Y
UNII	4G9EDB6V73 Y
DrugBank	DB03600
KEGG	C01571 Y
ChEBI	CHEBI:30813 Y
ChEMBL	CHEMBL107498 Y
Jmol-3D images	Image 1
SMILES O=C(O)CCCCCCCCC
InChI InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12) Y Key: GHVNFZFCNZKVNT-UHFFFAOYSA-N Y InChI=1/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12) Key: GHVNFZFCNZKVNT-UHFFFAOYAC
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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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

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

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

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

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

1. ↑ Decanoic acid
2. ↑ 2.0 2.1 "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