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es toggle the table of contents 1 pentadecanol 11 languages العربية čeština deutsch esperanto español فارسی bahasa indonesia русский اردو 吴语 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia 15 carbon alcohol 1 pentadecanol names preferred iupac name pentadecan 1 ol other names pentadecyl alcohol 1 n pentadecanol 2 identifiers cas number 629 76 5 3d model jsmol interactive image chebi chebi 77468 chembl chembl26561 chemspider 11891 echa infocard 100 010 099 ec number 211 107 9 pubchem cid 12397 unii 333qva4g2q comptox dashboard epa dtxsid0027270 inchi inchi 1s c15h32o c1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 h16h 2 15h2 1h3 key reiuxolghvxaeo uhfffaoysa n smiles ccccccccccccccco properties chemical formula c 15 h 32 o molar mass 228 420 g mol 1 appearance white solid density 0 842 kg 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 ghs labelling pictograms the template below ghs exclamation mark is being considered for merging with ghs pictogram see templates for discussion to help reach a consensus the template below ghs environment is being considered for merging with ghs pictogram see templates for discussion to help reach a consensus signal word warning hazard statements h315 h319 h410 h411 precautionary statements 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 their standard state at 25 c 77 f 100 kpa infobox references chemical compound 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 consisting of a pentadecane chain with a hydroxy group as substituent on one end it is an achiral molecule meaning that it has no mirror image isomers 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 adding ethylene oxide and sulfation adding a sulfo group reactions to produce surfactants primarily detergents 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 shell recommends 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 or dry chemical type fire extinguishers are recommended 7 in their product literature shell claims that high chain primary alcohols in the c 9 c 17 range are readily biodegradable and unlikely to bioaccumulate 3 7 they are not corrosive to carbon steel storage containers or process equipment and are compatible with a variety of polymers shell recommends tetrafluoroethylene high density polyethylene polypropylene and butyl rubber as gasketing materials ethylene propene diene monomer epdm rubber however cannot be used 7 compared to other 1 alkanols 1 nonanol 1 undecanol and 1 tridecanol 1 pentadecanol possesses lower solubility in supercritical 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 3 k at standard 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 5 k differential thermal analysis measurements on 1 pentadecanol were performed at temperatures from 300 to 370 k and pressures of up to 250 mpa 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 by dielectric measurements that confirmed its orientational disorder no triple point exists for 1 pentadecanol 9 synthesis edit the alcohol was discovered in 1893 by angelo simonini a student of adolf lieben at the university of vienna who used a variation of what s known as hunsdiecker reaction often called simonini reaction to get pentadecyl palmitate from silver palmitate and iodine at 100 c 10 2 c 15 h 31 cooag i 2 c 15 h 31 cooc 15 h 31 co 2 2 agi industrial production edit 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 6 natural occurrence edit 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 11 in 2008 a synthesis of pachastrissamine a cytotoxic lipid compound found in sea sponges 12 was described starting from 1 pentadecanol 5 fungal oxidization and assimilation of pentadecane has been observed by two citric acid producing candida strains wild type ksh 21 and mutant 337 transforming it into both pentadecanol and pentadecanoic acid through oxidization at one of the terminal carbon atoms 13 the highest conversion to pentadecanol seen in the 1977 study was from a 3 day fermenter culture of the 337 strain in which 85 5 mg was developed per 10 g of pentadecane some conversion to 2 pentadecanol and 2 pentadecanone was also observed 13 applications edit in a 1981 paper the activities of various primary alcohols were evaluated as substrates for alkyl dhap synthase s catalysis of fatty alcohol with acyl dihydroxyacetone phosphate in erlich 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 2 mol min mg protein 14 a 1994 study evaluated 1 pentadecanol as a potential anti acne agent while primary alcohols were known to be effective against gram positive bacteria it was previously found that free fatty acids and alcohols between c 8 and c 14 were skin irritants since the effect had ended at c 15 several longer chain alcohols were evaluated for their activity against propionibacterium acnes 1 pentadecanol was found to have a minimum inhibitory concentration mic of 0 78 μg ml and a minimum bactericidal concentration of 1 56 μg ml 15 in a 1995 paper by the same research group the 0 78 μg ml mic against p acnes was replicated and remained the lowest mic against p acnes among all primary alcohols tested from c 6 to c 20 1 pentadecanol was additionally found to have a mic of 6 25 μg ml against brevibacterium ammoniagenes and a mic greater than 800 μg ml essentially no effect against the dermatomycotic yeast pityrosporum ovale it along with 1 hexadecanol was found to be selectively antimicrobial against p acnes and not other gram positive bacteria unlike other alcohols like 1 dodecanol that were more broadly antimicrobial to all gram positive bacteria 16 a 2018 computational chemistry study investigated possible uses of alcohol compounds as mycobactericidal disinfectants for the control of mycobacterium tuberculosis the study computationally evaluated gibbs free energy g for the molecular docking of alcohols c 1 methanol to c 15 pentadecanol as ligands of the inha maba and pank receptors the observed trend was that binding energy between ligand and receptor increased with chain length pentadecanol the longest alcohol tested had a g computationally estimated as 4 9 kcal mol with inha 4 9 kcal mol with maba and 5 5 kcal mol with pank this was compared with triclosan whose g for those bindings is 6 4 kcal mol 6 7 kcal mol and 7 0 kcal 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 17 the properties of fluorinated 1 pentadecanols have been investigated as potential amphiphilic species for aiding adsorption of the pulmonary surfactant dipalmitoylphosphatidylcholine dppc dppc while contributing to film rigidity on the surface of alveoli has poor adsorption and respreading qualities highly fluorinated amphiphiles can compatibilize it to other surfaces but at the cost of bioaccumulation both in the human body and in the environment therefore the interaction of several partially fluorinated 1 pentadecanols with dppc in a langmuir monolayer was analyzed in a 2018 paper the molecules were c 4 f 9 ch 2 11 oh c 6 f 13 ch 2 9 oh and c 8 f 17 ch 2 7 oh as the fluorination degree increased so did hydrophobicity 18 references edit 1 2 3 4 sigma aldrich 1 pentadecanol archived from the original on 2019 08 24 retrieved 2019 08 23 chemspider 1 pentadecanol archived from the original on 2019 08 24 retrieved 2019 08 23 1 2 3 4 neodol 5 technical datasheet pdf shell global january 2021 archived pdf from the original on 14 march 2021 retrieved 8 march 2021 sigma aldrich msds 412228 archived from the original on 2020 09 01 retrieved 2019 08 23 1 2 venkatesan 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 1 2 shell global neodol alcohols and ethyxolates archived from the original on 2019 08 24 retrieved 2019 08 23 1 2 3 4 storage and handling of neodol alcohols pdf shell global june 2009 archived pdf from the original on 24 august 2019 retrieved 8 march 2021 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 1 2 reuter jörg würflinger albert october 1995 differential thermal analysis of long chain n alcohols under high pressure berichte der bunsengesellschaft für physikalische chemie 99 10 1247 1251 doi 10 1002 bbpc 199500067 simonini angelo 1893 über den abbau der fetten säuren zu kohlenstoffärmeren alkoholen monatshefte für chemie und verwandte teile anderer wissenschaften in german 14 1 81 92 doi 10 1007 bf01517859 issn 1434 4475 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 s2cid 14862566 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 pmc 5538274 pmid 28572516 s2cid 4437822 1 2 souw p luftmann h rehm h j 1977 oxidation of n alkanes by citric acid producing candida spp european journal of applied microbiology and biotechnology 3 4 289 301 doi 10 1007 bf01263329 s2cid 43536146 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 pmid 7030211 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 pmid 8158169 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 pmid 7582963 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 retrieved 8 march 2021 v t e alcohols by consumption alcohols found in alcoholic drinks 1 propanol 2 methyl 1 butanol ethanol isoamyl alcohol isobutanol phenethyl alcohol tert amyl alcohol tert butyl alcohol tryptophol medical alcohol ethchlorvynol methylpentynol methanol poisoning ethanol toxic alcohols isopropyl alcohol methanol primary alcohols 1 methanol 4 methylcyclohexanemethanol aminomethanol cyclohexylmethanol methoxymethanol methylazoxymethanol trifluoromethanol ethanol 1 aminoethanol 2 2 2 trichloroethanol 2 2 2 trifluoroethanol 2 2 ethoxyethoxy ethanol 2 2 methoxyethoxy ethanol 2 2 methoxyethoxy ethanol 2 butoxyethanol 2 chloroethanol 2 ethoxyethanol 2 fluoroethanol 2 mercaptoethanol 2 methoxyethanol aminoethylethanolamine diethylethanolamine dimethylethanolamine ethanol ethanolamine n n diisopropylaminoethanol n methylethanolamine phenoxyethanol tribromoethanol butanol 2 methyl 1 butanol isobutanol n butanol straight chain saturated c 1 c 9 methanol ethanol 1 propanol 1 butanol 1 pentanol 1 hexanol 1 heptanol 1 octanol capryl 1 nonanol pelargonic straight chain saturated c 10 c 19 1 decanol capric 1 undecanol hendecyl 1 dodecanol lauryl 1 tridecanol 1 tetradecanol myristyl 1 pentadecanol 1 hexadecanol cetyl palmityl 1 heptadecanol 1 octadecanol stearyl 1 nonadecanol straight chain saturated c 20 c 29 1 icosanol arachidyl 1 heneicosanol 1 docosanol behenyl 1 tricosanol 1 tetracosanol lignoceryl 1 pentacosanol 1 hexacosanol ceryl 1 heptacosanol 1 octacosanol cluytyl montanyl 1 nonacosanol straight chain saturated c 30 c 39 1 triacontanol melissyl myricyl 1 hentriacontanol 1 dotriacontanol lacceryl 1 tritriacontanol 1 tetratriacontanol geddyl 1 pentatriacontanol 1 hexatriacontanol 1 heptatriacontanol 1 octatriacontanol 1 nonatriacontanol straight chain saturated c 40 c 49 1 tetracontanol 1 hentetracontanol 1 dotetracontanol 1 tritetracontan...