1-Pentadecanol

1-Pentadecanol is an organic chemical compound classified as an alcohol. At room temperature, it is a white, flaky solid.[1] It is a saturated 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]

1-Pentadecanol
Names
Other names
Pentadecan-1-ol, pentadecyl alcohol,[1] n-pentadecanol[2]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.010.099
EC Number
  • 211-107-9
UNII
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
Safety data sheet [3]
GHS pictograms
GHS Signal word Warning
H315, H319, H400, H410, H411
P264, P273, P280, P302+352, P305+351+338, P321, P332+313, P337+313, P362, P391, P501
Flash point 112 C (closed cup)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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
  1. Sigma Aldrich. "1-Pentadecanol". Retrieved 2019-08-23.
  2. ChemSpider. "1-Pentadecanol". Retrieved 2019-08-23.
  3. Sigma Aldrich. "MSDS - 412228". Retrieved 2019-08-23.
  4. Venkatesan, K.; Srinivasan, K.V. (2008), "A novel stereoselective synthesis of pachastrissamine (jaspine B) starting from 1-pentadecanol", Tetrahedron: Asymmetry (2 ed.), 19 (2): 209–215, doi:10.1016/j.tetasy.2007.12.001
  5. Shell Global. "NEODOL Alcohols and Ethyxolates". Retrieved 2019-08-23.
  6. "Jaspine B induces non apoptotic cell death in gastric cancer cells independently of its inhibition of ceramide synthase".
  7. 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 ed.), American Chemical Society, 43 (6): 983–985, doi:10.1021/je980117r
  8. 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 ed.), Springer India, 71 (4): 313–319, doi:10.1007/s12595-017-0208-0


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