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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-12-01 23:02:43 UTC
HMDB IDHMDB01183
Secondary Accession NumbersNone
Metabolite Identification
Common NameOctanol
DescriptionOctanol occurs naturally in the form of esters in some essential oils. Octanol and water are immiscible. The distribution of a compound between water and octanol is used to calculate the partition coefficient (logP) of that molecule. Water/octanol partitioning is a good approximation of the partitioning between the cytosol and lipid membranes of living systems.(wikipedia). A colorless, slightly viscous liquid used as a defoaming or wetting agent. It is also used as a solvent for protective coatings, waxes, and oils, and as a raw material for plasticizers. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). It is also one of many compounds derived from tobacco and tobacco smoke and shown to increase the permeability of the membranes of human lung fibroblasts (PMID 7466833 ).
Structure
Thumb
Synonyms
  1. 1-Hydroxyoctane
  2. 1-Octanol
  3. 2-Capryl alcohol
  4. 2-Octanol
  5. 2-Octanol ~99%
  6. Alcohol C-8
  7. Alfol 8
  8. Capryl alcohol
  9. Caprylic alcohol
  10. DL-2-Octanol
  11. Dytol m-83
  12. Emery 3322
  13. Emery 3324
  14. Epal 8
  15. Heptyl carbinol
  16. Hexyl methyl carbinol
  17. Lorol 20
  18. Lorol C8
  19. N-Heptyl carbinol
  20. N-Octan-1-ol
  21. N-Octanol
  22. N-Octyl alcohol
  23. N-Octyl-alcohol
  24. Octan-1-ol
  25. Octan-2-ol
  26. Octan-2-ol 98+ %
  27. Octanol
  28. Octilin
  29. Octyl alcohol
  30. Octyl alcohol normal-primary
  31. Octyl-alcohol
  32. Prim-N-octyl alcohol
  33. Primary octyl alcohol
  34. Sipol L8
Chemical FormulaC8H18O
Average Molecular Weight130.2279
Monoisotopic Molecular Weight130.135765198
IUPAC Nameoctan-1-ol
Traditional Nameoctanol
CAS Registry Number111-87-5
SMILES
CCCCCCCCO
InChI Identifier
InChI=1S/C8H18O/c1-2-3-4-5-6-7-8-9/h9H,2-8H2,1H3
InChI KeyKBPLFHHGFOOTCA-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Alcohols
Sub ClassN/A
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Fatty alcohols(Lipidmaps)
  • a small molecule(Cyc)
  • octanol(ChEBI)
  • primary alcohol(ChEBI)
Substituents
  • Primary Alcohol
Direct ParentFatty Alcohols
Ontology
StatusDetected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Fatty acid metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-15.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.54 mg/mLNot Available
LogP3.00HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.53ALOGPS
logP3.21ALOGPS
logP2.58ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)16.84ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity40.54 m3·mol-1ChemAxon
Polarizability17.42 Å3ChemAxon
Spectra
SpectraGC-MSMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Feces
  • Urine
Tissue Location
  • Adipose Tissue
  • Brain
  • Fibroblasts
  • Intestine
  • Muscle
  • Placenta
  • Skin
  • Stratum Corneum
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative Colitis
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothBreast cancer details
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 IDFDB012583
KNApSAcK IDC00001264
Chemspider ID932
KEGG Compound IDC00756
BioCyc IDOCTANOL
BiGG IDNot Available
Wikipedia LinkOctanol
NuGOwiki LinkHMDB01183
Metagene LinkHMDB01183
METLIN ID6063
PubChem Compound957
PDB IDOC9
ChEBI ID16188
References
Synthesis ReferenceHagiwara, Nobue; Takahashi, Shigetoshi; Shibano, Toshishige. n-Octanol. Jpn. Tokkyo Koho (1977), 3 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Fujioka H, Murase K, Inoue T, Ishimaru Y, Akamune A, Yamamoto Y, Ikezoe J: A method for estimating the integral of the input function for the quantification of cerebral blood flow with 123I-IMP using one-point arterial blood sampling. Nucl Med Commun. 1998 Jun;19(6):561-6. Pubmed: 10234660
  2. Tuntland T, Odinecs A, Pereira CM, Nosbisch C, Unadkat JD: In vitro models to predict the in vivo mechanism, rate, and extent of placental transfer of dideoxynucleoside drugs against human immunodeficiency virus. Am J Obstet Gynecol. 1999 Jan;180(1 Pt 1):198-206. Pubmed: 9914604
  3. Okazawa H, Yonekura Y, Fujibayashi Y, Nishizawa S, Magata Y, Ishizu K, Tanaka F, Tsuchida T, Tamaki N, Konishi J: Clinical application and quantitative evaluation of generator-produced copper-62-PTSM as a brain perfusion tracer for PET. J Nucl Med. 1994 Dec;35(12):1910-5. Pubmed: 7989968
  4. Anderson BD, Raykar PV: Solute structure-permeability relationships in human stratum corneum. J Invest Dermatol. 1989 Aug;93(2):280-6. Pubmed: 2754277
  5. Bunge AL, Cleek RL: A new method for estimating dermal absorption from chemical exposure: 2. Effect of molecular weight and octanol-water partitioning. Pharm Res. 1995 Jan;12(1):88-95. Pubmed: 7724493
  6. Potts RO, Guy RH: Predicting skin permeability. Pharm Res. 1992 May;9(5):663-9. Pubmed: 1608900
  7. Poulin P, Schoenlein K, Theil FP: Prediction of adipose tissue: plasma partition coefficients for structurally unrelated drugs. J Pharm Sci. 2001 Apr;90(4):436-47. Pubmed: 11170034
  8. Southwell D, Barry BW: Penetration enhancers for human skin: mode of action of 2-pyrrolidone and dimethylformamide on partition and diffusion of model compounds water, n-alcohols, and caffeine. J Invest Dermatol. 1983 Jun;80(6):507-14. Pubmed: 6854051
  9. Barry BW, Bennett SL: Effect of penetration enhancers on the permeation of mannitol, hydrocortisone and progesterone through human skin. J Pharm Pharmacol. 1987 Jul;39(7):535-46. Pubmed: 2886623
  10. Fujioka H, Murase K, Inoue T, Ishimaru Y, Ebara H, Akamune A, Yamamoto Y, Mochizuki T, Ikezoe J: [Estimation of integral of input function for quantification of cerebral blood flow with N-isopropyl-p-[123I]iodoamphetamine using one-point venous blood sampling] Kaku Igaku. 1999 Oct;36(8):801-7. Pubmed: 10586540
  11. Ross1 JS, Shah JC: Reduction in skin permeation of N,N-diethyl-m-toluamide (DEET) by altering the skin/vehicle partition coefficient. J Control Release. 2000 Jul 3;67(2-3):211-21. Pubmed: 10825555
  12. Hadgraft J, Goosen C, du Plessis J, Flynn G: Predicting the dermal absorption of thalidomide and its derivatives. Skin Pharmacol Appl Skin Physiol. 2003 Mar-Apr;16(2):123-9. Pubmed: 12637788
  13. Al-Madhoun AS, Johnsamuel J, Barth RF, Tjarks W, Eriksson S: Evaluation of human thymidine kinase 1 substrates as new candidates for boron neutron capture therapy. Cancer Res. 2004 Sep 1;64(17):6280-6. Pubmed: 15342416
  14. Shun-xing L, Nan-sheng D, Feng-ying Z: Effect of digestive site acidity and compatibility on the species, lipopily and bioavailability of iron, manganese and zinc in Prunus persica Batsch and Carthamus tinctorus. Bioorg Med Chem Lett. 2004 Jan 19;14(2):505-10. Pubmed: 14698191
  15. Geyer H, Scheunert I, Korte F: Bioconcentration potential of organic environmental chemicals in humans. Regul Toxicol Pharmacol. 1986 Dec;6(4):313-47. Pubmed: 3101145
  16. Lange Y, Ye J, Steck TL: Activation of membrane cholesterol by displacement from phospholipids. J Biol Chem. 2005 Oct 28;280(43):36126-31. Epub 2005 Aug 29. Pubmed: 16129675
  17. Mantione KJ, Goumon Y, Esch T, Stefano GB: Morphine 6beta glucuronide: fortuitous morphine metabolite or preferred peripheral regulatory opiate? Med Sci Monit. 2005 May;11(5):MS43-46. Epub 2005 Apr 28. Pubmed: 15874899
  18. Stafford RG, Mehta M, Kemppainen BW: Comparison of the partition coefficient and skin penetration of a marine algal toxin (lyngbyatoxin A). Food Chem Toxicol. 1992 Sep;30(9):795-801. Pubmed: 1427518
  19. Makino K, Masuda Y, Gotoh S: [Measurement of regional cerebral blood flow using one-point arterial blood sampling and microsphere model with 123I-IMP: correction of one-point arterial sampling count by whole brain count ratio] Kaku Igaku. 1998 Jul;35(6):405-12. Pubmed: 9753919
  20. Zuo Y, Yeh JZ, Narahashi T: Octanol modulation of neuronal nicotinic acetylcholine receptor single channels. Alcohol Clin Exp Res. 2004 Nov;28(11):1648-56. Pubmed: 15547451
  21. Thelestam M, Curvall M, Enzell CR: Effect of tobacco smoke compounds on the plasma membrane of cultured human lung fibroblasts. Toxicology. 1980;15(3):203-17. Pubmed: 7466833

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate, myristate and palmitate. Has little activity toward prostaglandins A1 and E1. Oxidizes arachidonic acid to 20-hydroxyeicosatetraenoic acid (20-HETE).
Gene Name:
CYP4A11
Uniprot ID:
Q02928
Molecular weight:
59347.31
Reactions
Octane + reduced rubredoxin + Oxygen → Octanol + oxidized rubredoxin + Waterdetails
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate and palmitate. Shows no activity towards arachidonic acid and prostaglandin A1. Lacks functional activity in the kidney and does not contribute to renal 20-hydroxyeicosatetraenoic acid (20-HETE) biosynthesis.
Gene Name:
CYP4A22
Uniprot ID:
Q5TCH4
Molecular weight:
59245.28
Reactions
Octane + reduced rubredoxin + Oxygen → Octanol + oxidized rubredoxin + Waterdetails