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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:31:40 UTC
Update Date2022-03-07 02:52:14 UTC
HMDB IDHMDB0029632
Secondary Accession Numbers
  • HMDB0062710
  • HMDB29632
  • HMDB62710
Metabolite Identification
Common NameOleyl alcohol
DescriptionOleyl alcohol (also octadecenol or cis-9-octadecen-1-ol) is a non-ionic, unsaturated fatty alcohol. It is an emulsion stabilizer, antifoam agent, detergent, and release agent for food applications. Oleyl alcohol is found in fish oils and inedible beef fat. It belongs to the family of fatty alcohols. These are aliphatic alcohols consisting of a chain of 8 to 22 carbon atoms (do not have to bear a carboxylic acid group) (Wikipedia ).
Structure
Data?1582753444
Synonyms
ValueSource
(9Z)-9-Octadecen-1-olChEBI
(Z)-9-Octadecen-1-olChEBI
(Z)-9-OctadecenolChEBI
(Z)-Octadec-9-en-1-olChEBI
cis-9-Octadecen-1-olChEBI
cis-9-OctadecenolChEBI
cis-9-Octadecenyl alcoholChEBI
Witcohol 85Kegg
OleolHMDB
Oleyl alcohol, (Z)-isomerHMDB
(9Z)-Octadecen-1-olHMDB
(9Z)-Octadec-9-en-1-olHMDB
(Z)-Octadec-9-enolHMDB
9(Z)-Octadecen-1-olHMDB
9-Octadecen-1-olHMDB
Adol 34HMDB
Adol 80HMDB
Adol 85HMDB
Adol 90HMDB
Anjecol 90NHMDB
Anjecol 90NRHMDB
Atalco OHMDB
Cachalot O-1HMDB
Cachalot O-15HMDB
Cachalot O-3HMDB
Cachalot O-8HMDB
cis-Laquo deltaraquo 9-octadecenolHMDB
cis-Octadecen-1-olHMDB
Conditioner 1HMDB
Crodacol a.10HMDB
Crodacol-OHMDB
DermaffineHMDB
Fancol oa-95HMDB
Francol oa-95HMDB
H.D. eutanolHMDB
HD Oleyl alcohol 70/75HMDB
HD Oleyl alcohol 80/85HMDB
HD Oleyl alcohol 90/95HMDB
HD Oleyl alcohol CGHMDB
HD-Echelon 90/95HMDB
HD-EutanolHMDB
HD-Ocenol 90/95HMDB
HD-Ocenol KHMDB
LancolHMDB
Lipocol OHMDB
Loxanol 95HMDB
Loxanol mHMDB
NovolHMDB
OcenolHMDB
OceolHMDB
Octadec-9-en-1-olHMDB
Octadec-9Z-enolHMDB
OctadecenolHMDB
Oleic alcoholHMDB
Oleo alcoholHMDB
Oleoyl alcoholHMDB
Oleyl alcohol (NF)HMDB
Olive alcoholHMDB
SatolHMDB
Sipol OHMDB
Siponol OCHMDB
Unjecol 110HMDB
Unjecol 50HMDB
Unjecol 70HMDB
Unjecol 90HMDB
Witcohol 90HMDB
Oleyl alcoholChEBI
Chemical FormulaC18H36O
Average Molecular Weight268.4778
Monoisotopic Molecular Weight268.276615774
IUPAC Name(9Z)-octadec-9-en-1-ol
Traditional Nameconditioner 1
CAS Registry Number143-28-2
SMILES
CCCCCCCC\C=C/CCCCCCCCO
InChI Identifier
InChI=1S/C18H36O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h9-10,19H,2-8,11-18H2,1H3/b10-9-
InChI KeyALSTYHKOOCGGFT-KTKRTIGZSA-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
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point6.5 °CNot Available
Boiling Point207.00 °C. @ 13.00 mm HgThe Good Scents Company Information System
Water Solubility0.024 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP7.796 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.7e-05 g/LALOGPS
logP7.91ALOGPS
logP6.67ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)16.84ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity87.67 m³·mol⁻¹ChemAxon
Polarizability37.09 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+173.41531661259
DarkChem[M-H]-173.92731661259
DeepCCS[M+H]+176.07830932474
DeepCCS[M-H]-172.82730932474
DeepCCS[M-2H]-209.48730932474
DeepCCS[M+Na]+185.19230932474
AllCCS[M+H]+177.232859911
AllCCS[M+H-H2O]+174.132859911
AllCCS[M+NH4]+180.032859911
AllCCS[M+Na]+180.832859911
AllCCS[M-H]-177.632859911
AllCCS[M+Na-2H]-179.232859911
AllCCS[M+HCOO]-181.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Oleyl alcoholCCCCCCCC\C=C/CCCCCCCCO2122.4Standard polar33892256
Oleyl alcoholCCCCCCCC\C=C/CCCCCCCCO2012.0Standard non polar33892256
Oleyl alcoholCCCCCCCC\C=C/CCCCCCCCO2069.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oleyl alcohol,1TMS,isomer #1CCCCCCCC/C=C\CCCCCCCCO[Si](C)(C)C2142.4Semi standard non polar33892256
Oleyl alcohol,1TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCCO[Si](C)(C)C(C)(C)C2391.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Oleyl alcohol GC-MS (1 TMS)splash10-001j-9500000000-9817970c7d1b68f2bccf2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Oleyl alcohol EI-B (Non-derivatized)splash10-053s-9100000000-d8df7ab27573592064e62017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oleyl alcohol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ou-9730000000-dc2be84f918b8a55d7a72017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oleyl alcohol GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9431000000-c3888097425e557a6b652017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oleyl alcohol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oleyl alcohol 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 - Oleyl alcohol 10V, Positive-QTOFsplash10-0uxr-0190000000-3b216ec6d71eb9998e032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleyl alcohol 20V, Positive-QTOFsplash10-0udi-5790000000-f0ad0f4937df9c8267bf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleyl alcohol 40V, Positive-QTOFsplash10-052f-9820000000-d17a9f91b7264f1512792016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleyl alcohol 10V, Negative-QTOFsplash10-014i-0090000000-553073d99b67f184268e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleyl alcohol 20V, Negative-QTOFsplash10-014i-0090000000-5bbffeb7f9a05bde05182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleyl alcohol 40V, Negative-QTOFsplash10-000g-9860000000-2e95c189adc4e73f7c652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleyl alcohol 10V, Positive-QTOFsplash10-014i-4190000000-63789b3a849629ef04d72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleyl alcohol 20V, Positive-QTOFsplash10-0api-9210000000-4191049d1d23ffee30092021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleyl alcohol 40V, Positive-QTOFsplash10-0a4l-9000000000-a88ac09ef936fd6b3dba2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleyl alcohol 10V, Negative-QTOFsplash10-014i-0090000000-f8d52a37bd931625f1892021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleyl alcohol 20V, Negative-QTOFsplash10-014i-0090000000-e153b7a5d11b4114a0092021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oleyl alcohol 40V, Negative-QTOFsplash10-066u-6690000000-a3d12bef85e341d38e762021-09-24Wishart 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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID4447562
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOleyl_alcohol
METLIN IDNot Available
PubChem Compound5284499
PDB IDNot Available
ChEBI ID73504
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1270841
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.