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Decanoic acid

Names
IUPAC name Decanoic acid
Other names Capric acid n-Capric acid n-Decanoic acid Decylic acid n-Decylic acid C10:0 (Lipid numbers)
Identifiers
CAS Number	334-48-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:30813
ChEMBL	ChEMBL107498
ChemSpider	2863
DrugBank	DB03838
ECHA InfoCard	100.005.798
KEGG	C01571
PubChem CID	2969
UNII	4G9EDB6V73
CompTox Dashboard (EPA)	DTXSID9021554
InChI InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)Key: GHVNFZFCNZKVNT-UHFFFAOYSA-N InChI=1/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)Key: GHVNFZFCNZKVNT-UHFFFAOYAC
SMILES O=C(O)CCCCCCCCC
Properties
Chemical formula	C10H20O2
Molar mass	172.26 g/mol
Appearance	White crystals with strong smell
Density	0.893 g/cm, ?
Melting point	31.6 °C (304.8 K)
Boiling point	269 °C (542 K)
Solubility in water	immiscible
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Medium toxicity May cause respiratory irritation May be toxic on ingestion May be toxic on skin contact
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) 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. The term capric acid arises from the Latin "capric" which pertains to goats due to their olfactory similarities.

Capric acid occurs naturally in coconut oil and palm kernel oil, as well as in the milk of various mammals and to a lesser extent in other animal fats.

It is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals.

Two other acids are named after goats: caproic (C6) and caprylic (C8). 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 in an acetone solvent. This will give decanoic acid in up to 93% yield.

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.

Use

Manufacturing of esters for artificial fruit flavors and perfumes. Also as an intermediate in chemical syntheses.

References

1. http://www.sigmaaldrich.com/catalog/ProductDetail.do?N4=W236403%7CALDRICH&N5=Product%20No.%7CBRAND_KEY&F=SPEC
2. ^ "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry. 73 (4): 685–744. 2001. doi:10.1351/pac200173040685.
3. http://www.wordinfo.info/words/index/info/view_unit/371
4. http://www.chemicalland21.com/industrialchem/organic/CAPRIC%20ACID.htm
5. John McMurry (2008). Organic Chemistry 7th edition. Thompson - Brooks/Cole. Page 624

• Fatty acids