Pentadecylic acid
Chemical compound
From Wikipedia, the free encyclopedia
Pentadecylic acid, also known as pentadecanoic acid or C15:0, is an odd-chain saturated fatty acid. Its molecular formula is CH3(CH2)13CO2H. It is a colorless solid.
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 Pentadecanoic acid powder in weighboat | |
| Names | |
|---|---|
| Preferred IUPAC name
Pentadecanoic acid | |
| Other names
n-Pentadecanoic acid; C15:0 (Lipid numbers) | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.012.448 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C15H30O2 | |
| Molar mass | 242.403 g·mol−1 |
| Density | 0.842 g/cm3 |
| Melting point | 51 to 53 °C (124 to 127 °F; 324 to 326 K)[1] |
| Boiling point | 257 °C (495 °F; 530 K) (100 mmHg)[1] |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H315, H319, H335 | |
| P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501 | |
| Related compounds | |
Related compounds |
Tetradecanoic acid, Hexadecanoic acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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A laboratory preparation involves permanganate oxidation of 1-hexadecene (CH3(CH2)13CH=CH2).[2]
It is one of the most common odd-chain fatty acids, which are rare in nature.[3] Pentadecylic acid is found primarily in dairy fat, as well as in ruminant meat and some fish and plants.[4][5][6] The butterfat in cow milk is its major dietary source, comprising 1.2% of cow milk fat.[3][7]
Rare genetic disorders causing unusually high concentrations of C15:0 and C17:0, including Refsum disease, Zellweger syndrome, and propionic acidemia, confirmed endogenous synthesis of these odd-chain FAs in humans,[8] involving alpha oxidation.[9]
Research
Pentadecanoic acid has been compared to eicosapentaenoic acid (EPA) to evaluate the possibility that pentadecanoic acid is a previously unrecognized essential fatty acid.[10]