Showing Compound Card for n-Dodecanol (CDB005742)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (5) Show 5 proteinsXML
Record Information
Version1.0
Created at2020-04-27 16:51:12 UTC
Updated at2021-01-04 18:49:13 UTC
CannabisDB IDCDB005742
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namen-Dodecanol
DescriptionDodecanol, also known as 1-Dodecanol, Dodecyl alcohol or Lauryl 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. Thus, Dodecanol is a saturated 12-carbon fatty alcohol. Dodecanol exists as a colourless solid that is practically insoluble (in water). It is a very hydrophobic molecule and relatively neutral. Dodecanol has an earthy, fatty, honey or floral odor and a waxy greasy, cilantro-like taste. It is used as a flavor enhancer in food additives. Dodecanol is produced industrially from palm kernel or coconut oil fatty acids. Dodecanol is also used to make surfactants, lubricating oils and pharmaceuticals. It is also used in cosmetics as an emollient or emulsifying agent. Specifically, it is uses as an emulsion stabilizer for creams and lotions, a quality modifier of lipsticks, and and additive for ointment base and cream conditioners. Sulfate esters of Dodecanol (lauryl alcohol), especially sodium lauryl sulfate, are very widely used as surfactants. Sodium lauryl sulfate, ammonium lauryl sulfate, and sodium laureth sulfate are all used in shampoos. Dodecanol occurs naturally and has been detected, but not quantified in, several different foods, such as coriander, lime oil, mandarin oranges, watermelon, wine hyssops, pulses, quinoa, mamey sapotes, and agaves. This could make dodecanol a potential biomarker for the consumption of these foods. Dodecanol is a constituent of marijuana (cannabis) smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-DodecanolChEBI
1-HydroxydodecaneChEBI
Dodecyl alcoholChEBI
DodecylalcoholChEBI
Lauroyl alcoholChEBI
Lauryl alcoholChEBI
N-Dodecan-1-olChEBI
N-Lauryl alcoholChEBI
Undecyl carbinolChEBI
1-Dodecanol (acd/name 4.0)HMDB
1-Dodecyl alcoholHMDB
Alcohol C-12HMDB
Alfol 12HMDB
CO-1214S1-DodecanolHMDB
Dodecan-1-olHMDB
Dodecanol-1HMDB
Duodecyl alcoholHMDB
Dytol J-68HMDB
Epal 12HMDB
Exxal 12HMDB
Fatty alcoholHMDB
HydroxydodecaneHMDB
Karukoru 20HMDB
Lauric alcoholHMDB
Laurinic alcoholHMDB
Lauryl 24HMDB
Lipocol LHMDB
LorolHMDB
Lorol 11HMDB
Lorol 5HMDB
Lorol 7HMDB
Lorol C12HMDB
Lorol C12-C14HMDB
Lorol C8-C10 specialHMDB
Lorol specialHMDB
N-DodecanolHMDB
N-Dodecyl alcoholHMDB
Philcohol 1200HMDB
PisolHMDB
Sipol L12HMDB
Siponol 25HMDB
Siponol L5HMDB
Alcohol, laurylHMDB
Alcohol, N-dodecylHMDB
N Dodecyl alcoholHMDB
1 DodecanolHMDB
Alcohol, dodecylHMDB
DodecanolMeSH
Chemical FormulaC12H26O
Average Molecular Weight186.33
Monoisotopic Molecular Weight186.1984
IUPAC Namedodecan-1-ol
Traditional Name1-dodecanol
CAS Registry Number112-53-8
SMILES
CCCCCCCCCCCCO
InChI Identifier
InChI=1S/C12H26O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h13H,2-12H2,1H3
InChI KeyLQZZUXJYWNFBMV-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

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point24 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0Not Available
logP5.13HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP5.36ALOGPS
logP4.36ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)16.84ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity58.94 m³·mol⁻¹ChemAxon
Polarizability25.86 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSn-Dodecanol, non-derivatized, GC-MS Spectrumsplash10-0a4l-9000000000-0265898e793080c75dbbSpectrum
GC-MSn-Dodecanol, non-derivatized, GC-MS Spectrumsplash10-0f77-8940000000-2abf487d7e89251137efSpectrum
GC-MSn-Dodecanol, non-derivatized, GC-MS Spectrumsplash10-0a4l-9000000000-0265898e793080c75dbbSpectrum
GC-MSn-Dodecanol, non-derivatized, GC-MS Spectrumsplash10-0f77-8940000000-2abf487d7e89251137efSpectrum
Predicted GC-MSn-Dodecanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06sd-9400000000-0681b7adc8cc9fd058b2Spectrum
Predicted GC-MSn-Dodecanol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9410000000-3be1f4eaef8864e62784Spectrum
Predicted GC-MSn-Dodecanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0900000000-b353a8cde4c2b94724542015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-4900000000-d1156f91488d7ad627022015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9200000000-faaf592e90d4e52568092015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-1df3af150cb9112108462015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-672c4115ccf8141edd0e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mx-9800000000-241b553367aa990c7d8a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-8beace172044857b51842021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-ecedb7c9fabda3f671c42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abl-9700000000-6b6d1aed073a3e1bf7552021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-059i-9200000000-549932eca7a6f43070b92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-db132380640001bc6d9a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-eed549326da02bf14f6e2021-09-22View Spectrum
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 IDHMDB0011626
DrugBank IDDB06894
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030246
KNApSAcK IDC00030152
Chemspider ID7901
KEGG Compound IDC02277
BioCyc IDCPD-7867
BiGG IDNot Available
Wikipedia LinkDodecanol
METLIN IDNot Available
PubChem Compound8193
PDB IDNot Available
ChEBI ID28878
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