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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-01-30 15:39:15 UTC
Update Date2022-03-07 02:51:12 UTC
HMDB IDHMDB0011638
Secondary Accession Numbers
  • HMDB11638
Metabolite Identification
Common NameTetradecanol
Description1-Tetradecanol, or commonly myristyl alcohol, is a straight-chain saturated fatty alcohol, with the molecular formula C14H30O. It is a white crystalline solid that is practically insoluble in water, soluble in diethyl ether, and slightly soluble in ethanol. 1-Tetradecanol may be prepared by the reduction of myristic acid or some fatty acid esters with reagents such as lithium aluminium hydride or sodium. As with other fatty alcohols, 1-tetradecanol is used as an ingredient in cosmetics such as cold creams for its emollient properties. It is also used as an intermediate in the chemical synthesis of other products such sulfated alcohol (Wikipedia ).
Structure
Data?1582752932
Synonyms
ValueSource
1-HydroxytetradecaneChEBI
1-TetradecanolChEBI
1-Tetradecyl alcoholChEBI
Myristic alcoholChEBI
Myristyl alcoholChEBI
N-TetradecanolChEBI
N-Tetradecanol-1ChEBI
N-Tetradecyl alcoholChEBI
Tetradecyl alcoholChEBI
Adol 18HMDB
Alfol 14HMDB
Conol 1495HMDB
Kalcohl 40HMDB
Kalcohl 4098HMDB
Kalcol 4098HMDB
Lanette 14HMDB
Lanette KHMDB
Lanette wax KSHMDB
Lorol C 14HMDB
Loxanol VHMDB
N-Tetradecan-1-olHMDB
Nacol 14-95HMDB
Tetradecanol (7ci)HMDB
Tetradecan-1-olHMDB
Myristyl alcohol, aluminum saltHMDB
TetradecanolChEBI
Chemical FormulaC14H30O
Average Molecular Weight214.3874
Monoisotopic Molecular Weight214.229665582
IUPAC Nametetradecan-1-ol
Traditional Namemyristyl alcohol
CAS Registry Number112-72-1
SMILES
CCCCCCCCCCCCCCO
InChI Identifier
InChI=1S/C14H30O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h15H,2-14H2,1H3
InChI KeyHLZKNKRTKFSKGZ-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
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point39.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP6.03BURKHARD,LP ET AL. (1985B)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00044 g/LALOGPS
logP6.21ALOGPS
logP5.25ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)16.84ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity68.14 m³·mol⁻¹ChemAxon
Polarizability30.11 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+155.63431661259
DarkChem[M-H]-155.77531661259
DeepCCS[M+H]+158.06330932474
DeepCCS[M-H]-154.10130932474
DeepCCS[M-2H]-191.67730932474
DeepCCS[M+Na]+167.3430932474
AllCCS[M+H]+159.432859911
AllCCS[M+H-H2O]+155.932859911
AllCCS[M+NH4]+162.632859911
AllCCS[M+Na]+163.532859911
AllCCS[M-H]-160.832859911
AllCCS[M+Na-2H]-162.132859911
AllCCS[M+HCOO]-163.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TetradecanolCCCCCCCCCCCCCCO2220.7Standard polar33892256
TetradecanolCCCCCCCCCCCCCCO1673.9Standard non polar33892256
TetradecanolCCCCCCCCCCCCCCO1680.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tetradecanol,1TMS,isomer #1CCCCCCCCCCCCCCO[Si](C)(C)C1764.6Semi standard non polar33892256
Tetradecanol,1TBDMS,isomer #1CCCCCCCCCCCCCCO[Si](C)(C)C(C)(C)C1986.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Tetradecanol GC-MS (1 TMS)splash10-00di-7590000000-977855648ce1bb3be3472014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tetradecanol EI-B (Non-derivatized)splash10-0a4l-9000000000-32d5eef1c4d74b3ec3ba2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tetradecanol EI-B (Non-derivatized)splash10-052f-9000000000-acacbf10a3263c94194f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tetradecanol EI-B (Non-derivatized)splash10-0a5c-9100000000-2616129ec4a43b6c01022017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tetradecanol GC-MS (Non-derivatized)splash10-00di-7590000000-977855648ce1bb3be3472017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetradecanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0563-9600000000-eec06d9397af9c3a7e992017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetradecanol GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9620000000-4b25e0c0e809382e82172017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetradecanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetradecanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetradecanol NA , positive-QTOFsplash10-006x-4900000000-9984d821b36fbb9446e62020-07-21HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanol 10V, Positive-QTOFsplash10-00kb-0960000000-3c72c9bef17048b10a312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanol 20V, Positive-QTOFsplash10-0002-4910000000-9c450227835d31d57a2a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanol 40V, Positive-QTOFsplash10-052f-9300000000-e8c01d4094b22e4ad7a02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanol 10V, Negative-QTOFsplash10-03di-0390000000-24c96d483d78255edac32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanol 20V, Negative-QTOFsplash10-03di-1980000000-7c6d57144abbe039abdd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanol 40V, Negative-QTOFsplash10-000w-8900000000-c66ca1bb8fdb18f90e992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanol 10V, Positive-QTOFsplash10-014i-9340000000-c451e7bae87af519149a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanol 20V, Positive-QTOFsplash10-0ab9-9000000000-2e144a890203dcbb17fb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanol 40V, Positive-QTOFsplash10-052f-9000000000-cbaa89cc20f0bcb181ab2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanol 10V, Negative-QTOFsplash10-03di-0090000000-66f23677a88c1ed924762021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanol 20V, Negative-QTOFsplash10-03di-0090000000-d479398c0f5329e2e2922021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetradecanol 40V, Negative-QTOFsplash10-08fu-9640000000-3871dae38884d89b8f4d2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified6452.494-293269.723 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified0-1246326.354 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease
details
Associated Disorders and Diseases
Disease References
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002891
KNApSAcK IDC00032309
Chemspider ID7917
KEGG Compound IDNot Available
BioCyc IDCPD-7875
BiGG IDNot Available
Wikipedia Link1-Tetradecanol
METLIN IDNot Available
PubChem Compound8209
PDB IDNot Available
ChEBI ID77417
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029970
Good Scents IDNot Available
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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in catalytic activity
Specific function:
1-acyl-glycerone 3-phosphate + a long-chain alcohol = an alkyl-glycerone 3-phosphate + a long-chain acid anion
Gene Name:
AGPS
Uniprot ID:
O00116
Molecular weight:
72911.2
General function:
Involved in catalytic activity
Specific function:
Catalyzes the reduction of saturated fatty acyl-CoA with chain length C16 or C18 to fatty alcohols.
Gene Name:
FAR1
Uniprot ID:
Q8WVX9
Molecular weight:
59356.25
General function:
Involved in catalytic activity
Specific function:
Catalyzes the reduction of fatty acyl-CoA to fatty alcohols. The preferred substrates are C16, C18, C18:1 and C18:2 but low activity can be observed with C10-C14 substrates.
Gene Name:
FAR2
Uniprot ID:
Q96K12
Molecular weight:
59437.92
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Acyltransferase that predominantly esterify long chain (wax) alcohols with acyl-CoA-derived fatty acids to produce wax esters. Wax esters are enriched in sebum, suggesting that it plays a central role in lipid metabolism in skin. Has a preference for arachidyl alcohol as well as decyl alcohol, demonstrating its relatively poor activity using saturated long chain alcohols (C16, C18, and C20).
Gene Name:
AWAT1
Uniprot ID:
Q58HT5
Molecular weight:
37758.815
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Acyltransferase that predominantly esterify long chain (wax) alcohols with acyl-CoA-derived fatty acids to produce wax esters. Wax esters are enriched in sebum, suggesting that it plays a central role in lipid metabolism in skin. Has no activity using decyl alcohol and significantly prefers the C16 and C18 alcohols. May also have 2-acylglycerol O-acyltransferase (MGAT) and acyl-CoA:retinol acyltransferase (ARAT) activities, to catalyze the synthesis of diacylglycerols and retinyl esters; however this activity is unclear in vivo.
Gene Name:
AWAT2
Uniprot ID:
Q6E213
Molecular weight:
38093.25