- Decanoic acid
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Decanoic acid Decanoic acidOther namesIdentifiers CAS number 334-48-5 PubChem 2969 ChemSpider 2863 UNII 4G9EDB6V73 DrugBank DB03838 KEGG C01571 ChEBI CHEBI:30813 ChEMBL CHEMBL107498 Jmol-3D images Image 1 - O=C(O)CCCCCCCCC
Properties Molecular formula C10H20O2 Molar mass 172.26 g/mol Appearance White crystals with strong smell Density 0.893 g/cm3, ? Melting point 31.6 °C (304.8 K) [2]
Boiling point 269 °C (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 contactRelated compounds Related fatty acids Caprylic acid
Lauric acidRelated compounds Decanol
Decanal(verify) (what is:
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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. 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 and palm kernel oil, as well as in the milk of various mammals and to a lesser extent in other animal fats.[2]
It is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals.[4]
Two other acids are named after goats: caproic (C6) and caprylic (C8). Along with decanoic acid, these total 15% in goat milk fat.
Contents
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.[5]
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
- ^ http://www.sigmaaldrich.com/catalog/ProductDetail.do?N4=W236403%7CALDRICH&N5=Product%20No.%7CBRAND_KEY&F=SPEC
- ^ a b "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry 73 (4): 685–744. 2001. doi:10.1351/pac200173040685. http://iupac.org/publications/pac/73/4/0685/.
- ^ http://www.wordinfo.info/words/index/info/view_unit/371
- ^ http://www.chemicalland21.com/industrialchem/organic/CAPRIC%20ACID.htm
- ^ John McMurry (2008). Organic Chemistry 7th edition. Thompson - Brooks/Cole. Page 624
Lipids: fatty acids Saturated VFA: Acetic (C2) · Propionic (C3) · Butyric (C4) · Valeric (C5) · Caproic (C6) · Enanthic (C7) · Caprylic (C8) · Pelargonic (C9) · Capric (C10) · Undecylic (C11) · Lauric (C12) · Tridecylic (C13) · Myristic (C14) · Pentadecanoic (C15) · Palmitic (C16) · Margaric (C17) · Stearic (C18) · Nonadecylic (C19) · Arachidic (C20) · Heneicosylic (C21) · Behenic (C22) · Tricosylic (C23) · Lignoceric (C24) · Pentacosylic (C25) · Cerotic (C26) · Heptacosylic (C27) · Montanic (C28) · Nonacosylic (C29) · Melissic (C30) · Hentriacontylic (C31) · Lacceroic (C32) · Psyllic (C33) · Geddic (C34) · Ceroplastic (C35) · Hexatriacontylic (C36)n−3 Unsaturated n−6 Unsaturated n−9 Unsaturated biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i Categories:- Fatty acids
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