1-Pentadecanol
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3D model (JSmol)
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| ChEBI | |
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| ChemSpider | |
| ECHA InfoCard | 100.010.099 |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| CH3(CH2)13CH2OH | |
| Molar mass | 228.41 g/mol[1] |
| Appearance | White solid |
| Melting point | 41-44 C[1] |
| Boiling point | 269-271 C[1] |
| Hazards | |
| GHS labelling: | |
 
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| Warning | |
| H315, H319, H410, H411 | |
| P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, P391, P501 | |
| Flash point | 112 C (closed cup) |
| Safety data sheet (SDS) | [3] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1-Pentadecanol is an organic chemical compound classified as an alcohol. At room temperature, it is a white, flaky solid.[1]
1-pentadecanol is a long-chain fatty alcohol, identical to pentadecane with one of its terminal hydrogen atoms replaced by a hydroxy group. It is an achiral molecule.[4]
The Shell corporation uses a proprietary process for the synthesis of 1-pentadecanol (referring to it by the trade name Neodol 5) via hydroformylation of olefins produced from ethylene.[5] Like other long-chain primary alcohols, it is used as an ingredient in industrial chemicals, lubricating oils, and consumer products such as lotions and creams. Additionally, it can be used as a feedstock for processes that use ethoxylation and sulfation reactions to produce surfactants.
In 2008, a synthesis of pachastrissamine (a cytotoxic lipid compound found in sea sponges[6]) was described starting from 1-pentadecanol.[4]
Compared to other 1-alkanols (1-nonanol, 1-undecanol, and 1-tridecanol), 1-pentadecanol possesses lower solubility in supercritical carbon dioxide, consistent with a general trend of decreased solubility in alcohols with longer chains.[7]
Small amounts of 1-pentadecanol have been found (using thin-layer chromatography and GC/MS) to naturally occur in the leaves of Solena amplexicaulis (creeping cucumber).[8]
References
- ^ a b c d e Sigma Aldrich. "1-Pentadecanol". Retrieved 2019-08-23.
- ^ ChemSpider. "1-Pentadecanol". Retrieved 2019-08-23.
- ^ Sigma Aldrich. "MSDS - 412228". Retrieved 2019-08-23.
- ^ a b Venkatesan, K.; Srinivasan, K.V. (2008), "A novel stereoselective synthesis of pachastrissamine (jaspine B) starting from 1-pentadecanol", Tetrahedron: Asymmetry, 19 (2) (2 ed.): 209–215, doi:10.1016/j.tetasy.2007.12.001
- ^ Shell Global. "NEODOL Alcohols and Ethyxolates". Retrieved 2019-08-23.
- ^ "Jaspine B induces non apoptotic cell death in gastric cancer cells independently of its inhibition of ceramide synthase".
- ^ Artal, Manuela; Pauchon, Veronique; Embid, José Muñoz; Jose, Jacques (1998), "Solubilities of 1-Nonanol, 1-Undecanol, 1-Tridecanol, and 1-Pentadecanol in Supercritical Carbon Dioxide at T = 323.15 K", Journal of Chemical & Engineering Data, 43 (6) (43 ed.), American Chemical Society: 983–985, doi:10.1021/je980117r
- ^ Barik, Anandamay; Azmi, Syed; Karmakar, Amarnath; Soumendranath, Chatterje (2018), "Antibacterial Activity of Long-Chain Primary Alcohols from 'Solena amplexicaulis' Leaves", Proceedings of the Zoological Society, 71 (4) (71 ed.), Springer India: 313–319, doi:10.1007/s12595-017-0208-0
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