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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-11-30 15:52:32 UTC
Update Date2021-10-13 05:38:47 UTC
HMDB IDHMDB0013299
Secondary Accession Numbers
  • HMDB13299
Metabolite Identification
Common NamePentadecanol
DescriptionPentadecanol is a C-15 fatty alcohol. Very long chain fatty alcohols (VLCFA), obtained from plant waxes and beeswax have been reported to lower plasma cholesterol in humans. They can be found in unrefined cereal grains, beeswax, and many plant-derived foods. Reports suggest that 5–20 mg per day of mixed C24–C34 alcohols, including octacosanol and triacontanol, lower low-density lipoprotein (LDL) cholesterol by 21%–29% and raise high-density lipoprotein cholesterol by 8%–15%. Wax esters are hydrolyzed by a bile salt-dependent pancreatic carboxyl esterase, releasing long chain alcohols and fatty acids that are absorbed in the gastrointestinal tract. Studies of fatty alcohol metabolism in fibroblasts suggest that very long chain fatty alcohols, fatty aldehydes, and fatty acids are reversibly inter-converted in a fatty alcohol cycle. The metabolism of these compounds is impaired in several inherited human peroxisomal disorders, including adrenoleukodystrophy and Sjögren-Larsson syndrome.
Structure
Data?1582753106
Synonyms
ValueSource
1-PentadecanolChEBI
N-1-PentadecanolChEBI
N-PentadecanolChEBI
Pentadecyl alcoholChEBI
1-Pentadecanol (acd/name 4.0)HMDB
N-PpentadecanolHMDB
Neodol 5HMDB
Pentadecan-1-olHMDB
Pentadecanol-(1)HMDB
Chemical FormulaC15H32O
Average Molecular Weight228.414
Monoisotopic Molecular Weight228.245315646
IUPAC Namepentadecan-1-ol
Traditional Name1-pentadecanol
CAS Registry Number629-76-5
SMILES
CCCCCCCCCCCCCCCO
InChI Identifier
InChI=1S/C15H32O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16/h16H,2-15H2,1H3
InChI KeyREIUXOLGHVXAEO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentLong-chain fatty alcohols
Alternative Parents
Substituents
  • Long chain fatty alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point45 - 46 °CNot Available
Boiling Point298.00 to 299.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.47 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.443 (est)The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00021 g/LALOGPS
logP10(6.6) g/LALOGPS
logP10(5.7) g/LChemAxon
logS10(-6) g/LALOGPS
pKa (Strongest Acidic)16.84ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity72.75 m³·mol⁻¹ChemAxon
Polarizability32.25 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+159.90431661259
DarkChem[M-H]-159.90631661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pentadecanol,1TMS,#1CCCCCCCCCCCCCCCO[Si](C)(C)C1859.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pentadecanol,1TBDMS,#1CCCCCCCCCCCCCCCO[Si](C)(C)C(C)(C)C2086.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Pentadecanol GC-MS (1 TMS)splash10-000i-4390000000-c990154497fc4edd1c8c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pentadecanol EI-B (Non-derivatized)splash10-052f-9000000000-71c3524a7341cdcd7eb62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pentadecanol EI-B (Non-derivatized)splash10-0a59-9100000000-24988e5c47c70540f9572017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pentadecanol GC-MS (Non-derivatized)splash10-000i-4390000000-c990154497fc4edd1c8c2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentadecanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0563-7900000000-f382fe4d6fcdf2765fa52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentadecanol GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-9640000000-1d704b4ecf35fdacef752017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pentadecanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentadecanol 10V, Positive-QTOFsplash10-03fr-0190000000-ee611c15179a824c82bb2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentadecanol 20V, Positive-QTOFsplash10-03di-6690000000-74523b8e4abb6fbf271b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentadecanol 40V, Positive-QTOFsplash10-052f-9400000000-97007448b6a7747a324f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentadecanol 10V, Negative-QTOFsplash10-004i-0190000000-852540d8fce73c1805342016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentadecanol 20V, Negative-QTOFsplash10-004i-1490000000-a3e7792864f9d4b0e9952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentadecanol 40V, Negative-QTOFsplash10-0005-8920000000-03c2eeaad6298ea7cbdd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentadecanol 10V, Negative-QTOFsplash10-004i-0090000000-80709c480470aec77e652021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentadecanol 20V, Negative-QTOFsplash10-004i-0090000000-d465ffbb4b35c4f2ad652021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentadecanol 40V, Negative-QTOFsplash10-004i-8950000000-eea3e889061a3d0dcb8f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentadecanol 10V, Positive-QTOFsplash10-004i-7290000000-c01e646a53d47b9b63132021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentadecanol 20V, Positive-QTOFsplash10-0a4i-9000000000-ff0e347de875baffbcca2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pentadecanol 40V, Positive-QTOFsplash10-0a4l-9000000000-cb3a6f5d101555cdce782021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB006219
KNApSAcK IDC00056073
Chemspider ID11891
KEGG Compound IDNot Available
BioCyc IDCPD-11595
BiGG IDNot Available
Wikipedia Link1-Pentadecanol
METLIN IDNot Available
PubChem Compound12397
PDB IDNot Available
ChEBI ID77468
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1156041
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.