Showing Compound Card for n-Tetradecanol (CDB005750)

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Record Information
Version1.0
Created at2020-04-27 16:52:00 UTC
Updated at2021-01-04 18:49:14 UTC
CannabisDB IDCDB005750
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namen-Tetradecanol
DescriptionTetradecanol, also known as 1-Tetradecanol, n-Tetradecanol or myristyl alcohol (from Myristica fragrans – the nutmeg plant), 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. n-Tetradecanol is a long chain fatty alcohol with a C-14 carbon backbone. Tetradecanol is a very hydrophobic molecule, practically insoluble in water and relatively neutral. It exists as a white crystalline solid that is soluble in diethyl ether, and slightly soluble in ethanol. Tetradecanol has a coconut, fruity aroma. Industrially, 1-Tetradecanol may be prepared by the hydrogenation of myristic acid (or its esters); myristic acid itself can be found in nutmeg (from where it gains its name) but is also present in palm kernel oil and coconut oil and it is from these that the majority of 1-tetradecanol is produced. 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. Tetradecanol occurs naturally in a number of plants or foods and is found in kohlrabis, star fruit and whiskey. This could make tetradecanol a potential biomarker for the consumption of these foods. n-Tetradecanol is a constituent of cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Chemical FormulaC14H30O
Average Molecular Weight214.39
Monoisotopic Molecular Weight214.2297
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point39.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP6.03BURKHARD,LP ET AL. (1985B)
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
MS/MS
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Alkyldihydroxyacetonephosphate synthase, peroxisomalAGPS2q31.2O00116 details
Fatty acyl-CoA reductase 1FAR111p15.2Q8WVX9 details
Fatty acyl-CoA reductase 2FAR212p11.22Q96K12 details
Acyl-CoA wax alcohol acyltransferase 1AWAT1Xq13.1Q58HT5 details
Acyl-CoA wax alcohol acyltransferase 2AWAT2Xq13.1Q6E213 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0011638
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Alkyldihydroxyacetonephosphate synthase, peroxisomal
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
Enzyme Details
2. Fatty acyl-CoA reductase 1
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
Enzyme Details
3. Fatty acyl-CoA reductase 2
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
Enzyme Details
4. Acyl-CoA wax alcohol acyltransferase 1
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
Enzyme Details
5. Acyl-CoA wax alcohol acyltransferase 2
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