Showing Compound Card for 1-Decanol (CDB005697)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (5) Show 5 proteinsXML
Record Information
Version1.0
Created at2020-04-27 16:46:38 UTC
Updated at2021-01-04 18:49:09 UTC
CannabisDB IDCDB005697
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name1-Decanol
DescriptionDecyl alcohol, also known as 1-decanol, n-decanol or capric alcohol is a straight chain fatty alcohol with ten carbon atoms and the molecular formula CH3(CH2)9OH. Decyl alcohol belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of at least six carbon atoms. Decyl alcohol exists as a clear, colorless liquid that is insoluble in water and has a strong fatty, waxy, orange or sweet odour. Decyl alcohol is a fatty, waxy, green or citrus tasting compound. Decyl alcohol exists in all eukaryotes, ranging from yeast to humans. Decyl alcohol is found in a few different foods, such as apples, grapefruit oil, lemon oil, limes, mandarin oranges, other “small” oranges (clementine, tangerine), and common oregano. Decyl alcohol has also been detected, but not quantified in, several different foods, such as white mustards, pear, tomato, asparagus, corianders, and wine. Industrially, Decyl alcohol is used in the manufacture of plasticizers, lubricants, surfactants and solvents. Its ability to permeate the skin has led to it being investigated as a penetration enhancer for transdermal drug delivery. 1-Decanol or Decyl alcohol is rapidly and readily absorbed from the gastrointestinal tract and extensively metabolised to decanoic acid, which may occur naturally in humans. 1-Decanol has low acute toxicity by the oral, dermal and inhalation routes. It has no genotoxic, carcinogenic or neurotoxic potential. 1-Decanol is also found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-DecanolChEBI
Capric alcoholChEBI
Caprinic alcoholChEBI
N-Decan-1-olChEBI
N-DecanolChEBI
N-Decyl alcoholChEBI
NonylcarbinolChEBI
1-Decanol (acd/name 4.0)HMDB
Agent 504HMDB
Alcohol C-10HMDB
Alcohol C10HMDB
Alfol 10HMDB
AntakHMDB
Decan-1-olHMDB
DecanolHMDB
Decanol-(1)HMDB
Decyl N- alcoholHMDB
Decylic alcoholHMDB
Epal 10HMDB
Lorol C10HMDB
N-Decatyl alcoholHMDB
Nonyl acarbinolHMDB
PanoramaHMDB
ParanolHMDB
Primary decyl alcoholHMDB
RoyaltacHMDB
Royaltac m-2HMDB
Royaltac-85HMDB
N-Decyl alcohol, titanium saltHMDB
N-Decyl alcohol, sodium saltHMDB
N-Decyl alcohol, aluminum saltHMDB
N-Decyl alcohol, magnesium saltHMDB
Decyl alcoholChEBI
Chemical FormulaC10H22O
Average Molecular Weight158.28
Monoisotopic Molecular Weight158.1671
IUPAC Namedecan-1-ol
Traditional Namedecanol
CAS Registry Number112-30-1
SMILES
CCCCCCCCCCO
InChI Identifier
InChI=1S/C10H22O/c1-2-3-4-5-6-7-8-9-10-11/h11H,2-10H2,1H3
InChI KeyMWKFXSUHUHTGQN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentFatty alcohols
Alternative Parents
Substituents
  • 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
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point6.9 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP4.57HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP4.24ALOGPS
logP3.47ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)16.84ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity49.74 m³·mol⁻¹ChemAxon
Polarizability21.63 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a5c-9000000000-272f50a180ec299d0ec72015-03-01View Spectrum
GC-MS1-Decanol, 1 TMS, GC-MS Spectrumsplash10-014i-9550000000-f65b23bed3c7332ceee0Spectrum
GC-MS1-Decanol, non-derivatized, GC-MS Spectrumsplash10-0a4l-9000000000-977ade63abeaf44185e1Spectrum
GC-MS1-Decanol, non-derivatized, GC-MS Spectrumsplash10-0006-4900000000-330dbcd21a1b1614fd5cSpectrum
GC-MS1-Decanol, non-derivatized, GC-MS Spectrumsplash10-0a4l-9000000000-9be0ff3e4ab1ad4e0e73Spectrum
GC-MS1-Decanol, non-derivatized, GC-MS Spectrumsplash10-0a4l-9000000000-c952708ac925d4cc26eeSpectrum
GC-MS1-Decanol, non-derivatized, GC-MS Spectrumsplash10-014i-9550000000-f65b23bed3c7332ceee0Spectrum
Predicted GC-MS1-Decanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-9300000000-4f25974761a05f07fb5bSpectrum
Predicted GC-MS1-Decanol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9300000000-a0ff161ecca9705cccf8Spectrum
Predicted GC-MS1-Decanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1-Decanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0900000000-22d5c1bf7e2f98f12a5d2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-066r-1900000000-2a2cfd23706a056627342012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0aor-1900000000-b5a1bff81d20fca506fa2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0a4l-9000000000-94ae00dedd4b2c0e14702012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - CI-B (HITACHI M-80) , Positivesplash10-0006-4900000000-46512c8da212f02c45202012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0a4l-9000000000-30ef9f97c51d859228de2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-0a4l-9000000000-809358e8e81b71b6637c2012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0900000000-1d90a5292f22c4b6647f2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-5900000000-87aff9ba820066d5eecd2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9100000000-bfa5e6b3603e54d852e62016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-8715d4ce9ae4d38e61fa2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-525584847451aad5b7202016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002p-9500000000-716f14aed4e58223fa3a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0abc-9100000000-2f897fafba3e3f2158d02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abc-9000000000-38aa5bf5b02583ded1cf2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-d43ed4e45d2bc52056c52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-bd409bb26135f37b4c812021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-d4baf00602259714506d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9200000000-ad40a15e127bab4769cb2021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
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 IDHMDB0011624
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012351
KNApSAcK IDC00030100
Chemspider ID7882
KEGG Compound IDC01633
BioCyc IDCPD-7867
BiGG IDNot Available
Wikipedia Link1-Decanol
METLIN IDNot Available
PubChem Compound8174
PDB IDDE1
ChEBI ID28903
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