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Record Information
Version3.6
Creation Date2009-01-29 15:55:51 UTC
Update Date2013-05-07 19:27:49 UTC
HMDB IDHMDB11619
Secondary Accession NumbersNone
Metabolite Identification
Common NameArachidyl alcohol
DescriptionArachidyl alcohol, also 1-icosanol, is a waxy substance used as an emollient in cosmetics. It is a straight-chain fatty alcohol (Wikipedia).
Structure
Thumb
Synonyms
  1. 1-Eicosanol
  2. 1-Icosanol
  3. 1-Icosanol (ACD/Name 4.0)
  4. 1-Prydroxyeicosane
  5. Arachic alcohol
  6. Arachidic alcohol
  7. Eicosan-1-ol
  8. Eicosanol
  9. Eicosanol-(1)
  10. Eicosyl alcohol
  11. N-1-Eicosanol
  12. N-Eicosanol
Chemical FormulaC20H42O
Average Molecular Weight298.5469
Monoisotopic Molecular Weight298.323565966
IUPAC Nameicosan-1-ol
Traditional IUPAC Namearachidyl alcohol
CAS Registry Number629-96-9
SMILES
CCCCCCCCCCCCCCCCCCCCO
InChI Identifier
InChI=1S/C20H42O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21/h21H,2-20H2,1H3
InChI KeyBTFJIXJJCSYFAL-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Alcohols
Sub ClassN/A
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Fatty alcohols(Lipidmaps)
  • a fatty alcohol(Cyc)
  • a long-chain alcohol(Cyc)
  • a primary alcohol(Cyc)
Substituents
  • Primary Alcohol
Direct ParentFatty Alcohols
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point66.1 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility2.720E-05 g/LALOGPS
logP8.9ALOGPS
logP7.92ChemAxon
logS-7ALOGPS
pKa (strongest acidic)16.84ChemAxon
pKa (strongest basic)-2ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area20.23ChemAxon
rotatable bond count18ChemAxon
refractivity95.75ChemAxon
polarizability42.94ChemAxon
Spectra
SpectraGC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB007106
KNApSAcK IDNot Available
Chemspider ID11898
KEGG Compound IDNot Available
BioCyc IDCPD-7869
BiGG IDNot Available
Wikipedia Linkarachidyl alcohol
NuGOwiki LinkHMDB11619
Metagene LinkHMDB11619
METLIN IDNot Available
PubChem Compound12404
PDB IDNot Available
ChEBI ID545111
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

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