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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-08-12 20:33:57 UTC
Update Date2019-07-23 05:45:47 UTC
HMDB IDHMDB0003424
Secondary Accession Numbers
  • HMDB03424
Metabolite Identification
Common Name1-Hexadecanol
DescriptionCetyl alcohol, also known as 1-hexadecanol and palmityl alcohol, is a solid organic compound and a member of the alcohol class of compounds. Its chemical formula is CH3(CH2)15OH. At room temperature, cetyl alcohol takes the form of a waxy white solid or flakes. It belongs to the group of fatty alcohols. With the demise of commercial whaling, cetyl alcohol is no longer primarily produced from whale oil, but instead either as an end-product of the petroleum industry, or produced from vegetable oils such as palm oil and coconut oil. Production of cetyl alcohol from palm oil gives rise to one of its alternative names, palmityl alcohol.
Structure
Data?1563860747
Synonyms
ValueSource
1-CetanolChEBI
1-Hexadecyl alcoholChEBI
16-HexadecanolChEBI
CetanolChEBI
Cetyl alcoholChEBI
CetylalkoholChEBI
HexadecanolChEBI
N-1-HexadecanolChEBI
N-Hexadecyl alcoholChEBI
Palmityl alcoholChEBI
1-Hexadecyl alcHMDB
1-HexanedecanolHMDB
1-HydroxyhexadecaneHMDB
AdolHMDB
Adol 52HMDB
Adol 52 NFHMDB
Adol 52nfHMDB
Adol 54HMDB
Alcohol C-16HMDB
Aldol 54HMDB
Alfol 16HMDB
Atalco CHMDB
C16 AlcoholHMDB
Cachalot C-50HMDB
Cachalot C-50 NFHMDB
Cachalot C-51HMDB
Cachalot C-52HMDB
Ceraphyl icaHMDB
CetaffineHMDB
CetalHMDB
Cetalol caHMDB
Cetostearyl alcoholHMDB
Cetyl alcohol NFHMDB
Cetylic alcoholHMDB
CetylolHMDB
Crodacol CHMDB
Crodacol C70HMDB
Crodacol C95NFHMDB
Crodacol-casHMDB
Crodacol-catHMDB
Cyclal cetyl alcoholHMDB
Dehydag wax 16HMDB
Dytol F-11HMDB
Elfacos CHMDB
Epal 16nfHMDB
EthalHMDB
EtholHMDB
Eutanol g16HMDB
Exxal 16HMDB
Fancol caHMDB
Fatty alcoholHMDB
Hexadecan-1-olHMDB
Hexadecanol NFHMDB
Hexadecyl alcoholHMDB
HyfatolHMDB
Hyfatol 16HMDB
Isocetyl alcoholHMDB
IsohexadecanolHMDB
Isohexadecyl alcoholHMDB
Lanette 16HMDB
Lanol CHMDB
Lipocol CHMDB
Lorol 24HMDB
Lorol C16HMDB
LorolL 24HMDB
Loxanol KHMDB
Loxanol K extraHMDB
Loxanwachs SKHMDB
Loxiol VPG 1743HMDB
Michel xo-150-16HMDB
Myristyl alcoholHMDB
N-Cetyl alcoholHMDB
N-Hexadecan-1-olHMDB
N-HexadecanolHMDB
Normal primary hexadecyl alcoholHMDB
Philcohol 1600HMDB
Product 308HMDB
Rita caHMDB
Siponol CCHMDB
Siponol wax-aHMDB
SSDHMDB
SSD RPHMDB
Cetyl alcohol, 14C-labeledHMDB
Cetyl alcohol, aluminum saltHMDB
1-HexadecanolChEBI
Chemical FormulaC16H34O
Average Molecular Weight242.4406
Monoisotopic Molecular Weight242.26096571
IUPAC Namehexadecan-1-ol
Traditional Namecetyl alcohol
CAS Registry Number36653-82-4
SMILES
CCCCCCCCCCCCCCCCO
InChI Identifier
InChI=1S/C16H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3
InChI KeyBXWNKGSJHAJOGX-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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point49.3 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.3e-05 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00018 g/LALOGPS
logP7.17ALOGPS
logP6.14ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)16.84ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity77.35 m³·mol⁻¹ChemAxon
Polarizability34.38 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0f72-7931000000-00a8faa3fd4f0c38a405JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0f6t-9531000000-0dc2948d10d835886750JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-1be6f87af09f0bc4339fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-83f0c3f9a7d1a2d70b83JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9100000000-51d2315e018d6ebbe25dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f72-7931000000-00a8faa3fd4f0c38a405JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f6t-9531000000-0dc2948d10d835886750JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f72-9821000000-ee82a405e4a854526b64JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bvl-7910000000-c4f032970214d082f3cfJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9640000000-6df3de611756e2218c31JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0udi-0910000000-b74545433556690d2c46JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0udi-0900000000-7aab213ad736e774476cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0udi-0900000000-55a8272e13510c85c06aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0a4l-9000000000-a4776db6cf6d30dfb50eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positivesplash10-0a4l-9000000000-83f0c3f9a7d1a2d70b83JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-HX-100) , Positivesplash10-0a59-9100000000-7ca85869bfef10e335f3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0190000000-b08f970abae4433e0d8bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-5690000000-d0c4cde89f48e5218c95JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9500000000-455427a3ee7620a41403JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-3fdb1b4b343c7ad295bfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0090000000-a848ffe1f9f31e21601cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01vp-9740000000-15fb3da54ceed633096bJSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0a5c-9000000000-f3299e52ea0593788e37JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
Tissue Locations
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB09494
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003051
KNApSAcK IDNot Available
Chemspider ID2581
KEGG Compound IDC00823
BioCyc IDCPD-348
BiGG IDNot Available
Wikipedia LinkCetyl_Alcohol
METLIN ID6927
PubChem Compound2682
PDB IDNot Available
ChEBI ID16125
References
Synthesis ReferenceMihalovici, Ar.; Bors, G. Preparation of cetyl alcohol. Curierul Farmaceutic (1938), 8(No. 6), 1-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Rizzo WB, Craft DA: Sjogren-Larsson syndrome: accumulation of free fatty alcohols in cultured fibroblasts and plasma. J Lipid Res. 2000 Jul;41(7):1077-81. [PubMed:10884288 ]
  2. Hargrove JL, Greenspan P, Hartle DK: Nutritional significance and metabolism of very long chain fatty alcohols and acids from dietary waxes. Exp Biol Med (Maywood). 2004 Mar;229(3):215-26. [PubMed:14988513 ]

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