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1-Hexadecanol (T3D4863)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (2)XML
Targets (2)
Record Information
Version2.0
Creation Date2014-09-11 05:19:47 UTC
Update Date2014-12-24 20:26:58 UTC
Accession NumberT3D4863
Identification
Common Name1-Hexadecanol
ClassSmall Molecule
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.
Compound Type
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
1-Cetanol
1-Hexadecyl alc
1-Hexadecyl alcohol
1-Hexanedecanol
1-Hydroxyhexadecane
16-Hexadecanol
Adol
Adol 52
Adol 52 NF
Adol 52NF
Adol 54
Alcohol C-16
Aldol 54
Alfol 16
Atalco C
C16 alcohol
Cachalot C-50
Cachalot C-50 NF
Cachalot C-51
Cachalot C-52
Ceraphyl ICA
Cetaffine
Cetal
Cetalol CA
Cetanol
Cetostearyl alcohol
Cetyl alcohol
Cetyl alcohol NF
Cetylic alcohol
Cetylol
Crodacol C
Crodacol C70
Crodacol C95NF
Crodacol-CAS
Crodacol-CAT
Cyclal cetyl alcohol
Dehydag wax 16
Dytol F-11
Elfacos C
Epal 16NF
Ethal
Ethol
Eutanol G16
Exxal 16
Fancol CA
Fatty alcohol
Hexadecan-1-ol
Hexadecanol
Hexadecanol NF
Hexadecyl alcohol
Hyfatol
Hyfatol 16
Isocetyl alcohol
Isohexadecanol
Isohexadecyl alcohol
Lanette 16
Lanol C
Lipocol C
Lorol 24
Lorol C16
LorolL 24
Loxanol K
Loxanol K extra
Loxanwachs SK
Loxiol VPG 1743
Michel XO-150-16
Myristyl alcohol
N-1-Hexadecanol
N-Cetyl alcohol
N-Hexadecan-1-ol
N-Hexadecanol
N-Hexadecyl alcohol
Normal primary hexadecyl alcohol
Palmityl alcohol
Philcohol 1600
Product 308
Rita CA
Siponol CC
Siponol wax-A
SSD
SSD RP
Chemical FormulaC16H34O
Average Molecular Mass242.441 g/mol
Monoisotopic Mass242.261 g/mol
CAS Registry Number36653-82-4
IUPAC Namehexadecan-1-ol
Traditional Namecetyl alcohol
SMILESCCCCCCCCCCCCCCCCO
InChI IdentifierInChI=1S/C16H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3
InChI KeyInChIKey=BXWNKGSJHAJOGX-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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Fibroblasts
Pathways
NameSMPDB LinkKEGG Link
Plasmalogen SynthesisSMP00479 Not Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point49.3 °C
Boiling PointNot Available
Solubility1.34e-05 mg/mL at 25 °C
LogPNot 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
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0f72-7931000000-00a8faa3fd4f0c38a4052014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0f6t-9531000000-0dc2948d10d8358867502014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-1be6f87af09f0bc4339f2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-83f0c3f9a7d1a2d70b832017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a59-9100000000-51d2315e018d6ebbe25d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f72-7931000000-00a8faa3fd4f0c38a4052017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f6t-9531000000-0dc2948d10d8358867502017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f72-9821000000-ee82a405e4a854526b642017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bvl-7910000000-c4f032970214d082f3cf2017-08-28View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9640000000-6df3de611756e2218c312017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0udi-0910000000-b74545433556690d2c462012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0udi-0900000000-7aab213ad736e774476c2012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0udi-0900000000-55a8272e13510c85c06a2012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0a4l-9000000000-a4776db6cf6d30dfb50e2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positivesplash10-0a4l-9000000000-83f0c3f9a7d1a2d70b832012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-HX-100) , Positivesplash10-0a59-9100000000-7ca85869bfef10e335f32012-08-31View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0190000000-b08f970abae4433e0d8b2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-5690000000-d0c4cde89f48e5218c952017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9500000000-455427a3ee7620a414032017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-3fdb1b4b343c7ad295bf2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0090000000-a848ffe1f9f31e21601c2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01vp-9740000000-15fb3da54ceed633096b2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-4190000000-44af6a0edc2288305d9c2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abc-9110000000-a07d84c82c62e530754e2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-dc9968082483b614a7232021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-3ce1eb2d48c904ebe3472021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0090000000-e0b832e3e0af19f4f9ae2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9880000000-0db321e9b8178e2cdc8f2021-09-23View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a5c-9000000000-f3299e52ea0593788e372014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not Available2012-12-05View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB03424
PubChem Compound ID2682
ChEMBL IDCHEMBL706
ChemSpider ID2581
KEGG IDC00823
UniProt IDNot Available
OMIM ID
ChEBI ID16125
BioCyc IDCPD-348
CTD IDNot Available
Stitch IDNot Available
PDB IDPL3
ACToR IDNot Available
Wikipedia Link1-Hexadecanol
References
Synthesis ReferenceMihalovici, Ar.; Bors, G. Preparation of cetyl alcohol. Curierul Farmaceutic (1938), 8(No. 6), 1-9.
MSDSLink
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. [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. [14988513 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Nuclear receptor ROR-beta
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds DNA as a monomer to ROR response elements (RORE) containing a single core motif half-site 5'-AGGTCA-3' preceded by a short A-T-rich sequence. Considered to have intrinsic transcriptional activity, have some natural ligands such as all-trans retinoic acid (ATRA) and other retinoids which act as inverse agonists repressing the transcriptional activity. Required for normal postnatal development of rod and cone photoreceptor cells. Modulates rod photoreceptors differentiation at least by inducing the transcription factor NRL-mediated pathway. In cone photoreceptor cells, regulates transcription of OPN1SW. Involved in the regulation of the period length and stability of the circadian rhythm. May control cytoarchitectural patterning of neocortical neurons during development. May act in a dose-dependent manner to regulate barrel formation upon innervation of layer IV neurons by thalamocortical axons. May play a role in the suppression of osteoblastic differentiation through the inhibition of RUNX2 transcriptional activity (By similarity).Isoform 1 is critical for hindlimb motor control and for the differentiation of amacrine and horizontal cells in the retina. Regulates the expression of PTF1A synergistically with FOXN4 (By similarity).
Gene Name:
RORB
Uniprot ID:
Q92753
Molecular Weight:
53219.385 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.567 uMATG_RORb_TRANSAttagene
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
Target Details
2. Cytochrome P450 2C19
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC509.82 uMNVS_ADME_hCYP2C19Novascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]