1-Pentadecanol
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| Preferred IUPAC name
Pentadecan-1-ol | |
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3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.010.099 |
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PubChemCID
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CompTox Dashboard(EPA)
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| Properties | |
| C15H32O | |
| Molar mass | 228.420g·mol−1 |
| Appearance | White solid |
| Density | 0.842kg/L at 40 °C[3] |
| Melting point | 41–44 °C (106–111 °F; 314–317 K)[1] |
| Boiling point | 269–271 °C (516–520 °F; 542–544 K)[1] |
| Hazards | |
| GHSlabelling: | |
 
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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 (234 °F; 385 K) closed cup |
| Safety data sheet(SDS) | [4] |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
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1-Pentadecanolis anorganicchemical compoundclassified as analcohol.At room temperature, it is a white, flaky solid.[1]It is asaturatedlong-chainfatty alcoholconsisting of apentadecanechain with ahydroxy groupassubstituenton one end. It is anachiralmolecule (meaning that it has nomirror-imageisomers).[5]
Like other long-chainprimary 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 afeedstockfor processes that useethoxylation(addingethylene oxide) andsulfation(adding asulfo group) reactions to producesurfactants(primarilydetergents).[6]
Properties
[edit]1-Pentadecanol is generally a stable compound. Like other long-chain primary alcohols, 1-pentadecanol exhibits low oral, skin and respiratory toxicity.[3]However, it may be slightly to moderately irritating to the eyes and skin, and prolonged contact with undiluted alcohols can lead to defatting of the skin.[3]Accordingly,Royal Dutch Shellrecommends that eye protection, chemical-resistant gloves, and other protective clothing be worn when handling large amounts of 1-pentadecanol.[7]It floats on water, and can catch fire under certain conditions; in the case of a fire,carbon dioxide,foam,sand,earth, ordry chemicaltypefire extinguishersare recommended.[7]
In their product literature, Shell claims that high-chain primary alcohols (in the C9–C17range) are "readily biodegradable and unlikely tobioaccumulate".[3][7]They are notcorrosivetocarbon steelstorage containers or process equipment, and are compatible with a variety of polymers; Shell recommendstetrafluoroethylene,high-density polyethylene,polypropyleneandbutyl rubberasgasketingmaterials.Ethylene propene-diene monomer(EPDM) rubber, however, cannot be used.[7]
Compared to other 1-alkanols (1-nonanol,1-undecanol,and1-tridecanol), 1-pentadecanol possesses lowersolubilityinsupercritical carbon dioxide.This is consistent with a general trend of decreased solubility in alcohols with longer chains.[8]
When cooling from a liquid state, 1-pentadecanol (at 316.3K,atstandard pressure) assumes a crystalline structure known as the α-form, a "rotator phase" in which molecules can rotate about their long axes. While other long-chain alcohols, cooling further from the α-form, experience a solid-state transition into either a γ-form (with chains tilted to the basal plane normal) or a β-form (with vertical chains), 1-pentadecanol has been observed to exclusively assume the β-form when cooling, which it does at 311.5K.Differential thermal analysismeasurements on 1-pentadecanol were performed at temperatures from 300 to 370K and pressures of up to 250MPa;on heating, it was observed to change from a crystalline phase (β-form) to a rotator phase (α-form) a few degrees below its melting point.[9]The observation of this rotator state in pentadecanol was substantiated bydielectricmeasurements that confirmed its orientational disorder. Notriple pointexists for 1-pentadecanol.[9]
Production
[edit]The Shell corporation uses a proprietary process for thesynthesisof 1-pentadecanol (referring to it by the trade name Neodol 5) viahydroformylationofolefinsproduced fromethylene.[6]
Small amounts of 1-pentadecanol have been found (usingthin-layer chromatographyandGC/MS) to naturally occur in the leaves ofSolena amplexicaulis(creeping cucumber).[10]In 2008, a synthesis ofpachastrissamine(acytotoxiclipidcompound found insea sponges[11]) was described starting from 1-pentadecanol.[5]
Fungal oxidizationand assimilation ofpentadecanehas been observed by twocitric acid-producingCandidastrains (wild typeKSH 21 andmutant337), transforming it into both pentadecanol andpentadecanoic acidthrough oxidization at one of the terminal carbon atoms.[12]The highest conversion to pentadecanol seen in the 1977 study was from a 3-dayfermenterculture of the 337 strain, in which 85.5mg was developed per 10g of pentadecane. Some conversion to2-pentadecanoland2-pentadecanonewas also observed.[12]
Applications
[edit]In a 1981 paper, the activities of various primary alcohols were evaluated assubstratesforalkyl DHAP synthase'scatalysisof fatty alcohol with acyldihydroxyacetone phosphateinErlich ascites tumor cells.The specificity of the cells' microsomal alkyl DHAP synthase with respect to different alcohols was investigated; pentadecanol had an activity of approximately 0.2mol/min/mg protein.[13]
A 1994 study evaluated 1-pentadecanol as a potentialanti-acneagent. While primary alcohols were known to be effective againstGram-positivebacteria, it was previously found that freefatty acidsand alcohols between C8and C14wereskin irritants.Since the effect had ended at C15,several longer-chain alcohols were evaluated for their activity againstPropionibacterium acnes;1-pentadecanol was found to have aminimum inhibitory concentration(MIC) of 0.78μg/mL and aminimum bactericidal concentrationof 1.56μg/mL.[14]
In a 1995 paper by the same research group, the 0.78μg/mL MIC againstP.acneswas replicated, and remained the lowest MIC againstP.acnesamong allprimary alcoholstested (from C6to C20). 1-Pentadecanol was, additionally, found to have a MIC of 6.25μg/mL againstBrevibacterium ammoniagenes,and a MIC greater than 800μg/mL (essentially, no effect) against thedermatomycoticyeastPityrosporum ovale.It, along with1-hexadecanol,was found to be selectively antimicrobial againstP. acnesand not other Gram-positive bacteria (unlike other alcohols, like1-dodecanol,that were more broadly antimicrobial to all Gram-positive bacteria).[15]
A 2018computational chemistrystudy investigated possible uses of alcohol compounds as mycobactericidal disinfectants for the control ofMycobacterium tuberculosis.The study computationally evaluatedGibbs free energy(∆G) for themolecular dockingof alcohols C1(methanol) to C15(pentadecanol) asligandsof theInhA,MabA,andPanKreceptors. The observed trend was thatbinding energybetween ligand and receptor increased with chain length; pentadecanol, the longest alcohol tested, had a ∆G computationally estimated as −4.9kcal/mol with InhA, −4.9kcal/mol with MabA, and −5.5kcal/mol with PanK. This was compared withtriclosan(whose ∆G for those bindings is −6.4kcal/mol, −6.7kcal/mol and −7.0kcal/mol respectively); pentadecanol was found to have "potency" as a mycobactericidal agent and suggested as a "reference" for further development of receptor-targeted mycobactericidal agents.[16]
The properties offluorinated1-pentadecanols have been investigated as potentialamphiphilicspecies for aidingadsorptionof thepulmonary surfactantdipalmitoylphosphatidylcholine(DPPC). DPPC, while contributing to film rigidity on the surface ofalveoli,has poor adsorption andrespreadingqualities; highly fluorinated amphiphiles cancompatibilizeit to other surfaces, but at the cost ofbioaccumulationboth in the human body and in the environment. Therefore, the interaction of several partially fluorinated 1-pentadecanols with DPPC in aLangmuir monolayerwas analyzed in a 2018 paper. The molecules were F4H11OH, F6H9OH, and F8H7OH; as the fluorination degree increased, so didhydrophobicity.[17]
References
[edit]- ^abcdSigma Aldrich."1-Pentadecanol".Archivedfrom the original on 2019-08-24.Retrieved2019-08-23.
- ^ChemSpider."1-Pentadecanol".Archivedfrom the original on 2019-08-24.Retrieved2019-08-23.
- ^abcd"NEODOL 5 Technical Datasheet"(PDF).Shell Global. January 2021.Archived(PDF)from the original on 14 March 2021.Retrieved8 March2021.
- ^Sigma Aldrich."MSDS - 412228".Archivedfrom the original on 2020-09-01.Retrieved2019-08-23.
- ^abVenkatesan, K.; Srinivasan, K. V. (2008), "A novel stereoselective synthesis of pachastrissamine (jaspine B) starting from 1-pentadecanol",Tetrahedron: Asymmetry,19(2): 209–215,doi:10.1016/j.tetasy.2007.12.001
- ^abShell Global."NEODOL Alcohols and Ethyxolates".Archivedfrom the original on 2019-08-24.Retrieved2019-08-23.
- ^abcd"Storage and handling of NEODOL alcohols"(PDF).Shell Global. June 2009.Archived(PDF)from the original on 24 August 2019.Retrieved8 March2021.
- ^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), American Chemical Society: 983–985,doi:10.1021/je980117r
- ^abReuter, Jörg; Würflinger, Albert (October 1995). "Differential Thermal Analysis of Long-Chainn-Alcohols under High Pressure ".Berichte der Bunsengesellschaft für physikalische Chemie.99(10): 1247–1251.doi:10.1002/bbpc.199500067.
- ^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), Springer India: 313–319,doi:10.1007/s12595-017-0208-0,S2CID14862566
- ^Cingolani, Francesca; Simbari, Fabio; Abad, Jose Luis; Casasampere, Mireia; Fabrias, Gemma; Futerman, Anthony H.; Casas, Josefina (2017)."Jaspine B induces non apoptotic cell death in gastric cancer cells independently of its inhibition of ceramide synthase".Journal of Lipid Research.58(8): 1500–1513.doi:10.1194/jlr.M072611.PMC5538274.PMID28572516.S2CID4437822.
- ^abSouw, P.; Luftmann, H.; Rehm, H. J. (1977). "Oxidation ofn-alkanes by citric acid producingCandidaspp ".European Journal of Applied Microbiology and Biotechnology.3(4): 289–301.doi:10.1007/BF01263329.S2CID43536146.
- ^Davis, Paul A.; Hajra, Amiya K. (November 12, 1980)."Assay and Properties of the Enzyme Catalyzing the Biosynthesis of 1-O-Alkyl Dihydroxyacetone 3-Phosphate "(PDF).Archives of Biochemistry and Biophysics.211(1): 20–29.doi:10.1016/0003-9861(81)90424-0.hdl:2027.42/24237.PMID7030211.Archived(PDF)from the original on 14 March 2021.
- ^Kubo, Isao; Muroi, Hisae; Kubo, Aya (January 1994). "Naturally Occurring Antiacne Agents".Journal of Natural Products.57(1): 9–17.doi:10.1021/np50103a002.PMID8158169.
- ^Kubo, Isao; Muroi, Hisae; Kubo, Aya (July 1995). "Structural functions of antimicrobial long-chain alcohols and phenols".Bioorganic & Medicinal Chemistry.3(7): 873–880.doi:10.1016/0968-0896(95)00081-Q.PMID7582963.
- ^Syahputra, Gita; Arwansyah, Wien Kusharyoto; Kusharyoto, Wien (2018)."Molecular Docking and Molecular Dynamics Study of Alcoholic Compounds as Mycobactericidal Agents Using InhA, MabA and PanK as Receptors".Annales Bogorienses.22(2): 101.doi:10.14203/ann.bogor.2018.v22.n2.101-115.
- ^Nakahara, Hiromichi; Shibata, Osamu (2018)."Miscibility of Semifluorinated Pentadecanol with DPPC at the Air−Water Interface"(PDF).Accounts of Materials & Surface Research.3(4): 199–208.Archived(PDF)from the original on 23 October 2020.Retrieved8 March2021.
