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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-15 04:56:50 UTC
NP-MRD IDNP0000037
Secondary Accession NumbersNone
Natural Product Identification
Common NameOctanol
Description1-Octanol, also known as octan-1-ol, is the organic compound with the molecular formula CH3(CH2)7OH. It is a fatty alcohol. Many other isomers are also known generically as octanols. Octanol is mainly produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the alkylaluminium products. This route is known as the Ziegler alcohol synthesis. Octanol also 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. Octanol is 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. 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
Data?1628564076
Synonyms
ValueSource
1-HydroxyoctaneChEBI
1-OctanolChEBI
1-OktanolChEBI
Capryl alcoholChEBI
Caprylic alcoholChEBI
N-Heptyl carbinolChEBI
N-Octan-1-olChEBI
Primary octyl alcoholChEBI
2-Capryl alcoholHMDB
2-OctanolHMDB
2-Octanol ~99%HMDB
Alcohol C-8HMDB
Alfol 8HMDB
DL-2-OctanolHMDB
Dytol m-83HMDB
Emery 3322HMDB
Emery 3324HMDB
Epal 8HMDB
Heptyl carbinolHMDB
Hexyl methyl carbinolHMDB
Lorol 20HMDB
Lorol C8HMDB
N-OctanolHMDB, MeSH
N-Octyl alcoholHMDB, MeSH
N-Octyl-alcoholHMDB
Octan-1-olHMDB
Octan-2-olHMDB
Octan-2-ol 98+ %HMDB
OctilinHMDB
Octyl alcoholHMDB
Octyl alcohol normal-primaryHMDB
Octyl-alcoholHMDB
Prim-N-octyl alcoholHMDB
Sipol L8HMDB
1 OctanolMeSH, HMDB
N OctanolMeSH, HMDB
Alcohol, N-octylMeSH, HMDB
N Octyl alcoholMeSH, HMDB
Chemical FormulaC8H18O
Average Mass130.2279 Da
Monoisotopic Mass130.13577 Da
IUPAC Nameoctan-1-ol
Traditional Nameoctanol
CAS Registry Number111-87-5
SMILES
[H]OC([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]
InChI Identifier
InChI=1S/C8H18O/c1-2-3-4-5-6-7-8-9/h9H,2-8H2,1H3
InChI KeyKBPLFHHGFOOTCA-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Anthemis aciphylla BOISS.var.discoidea BOISSKNApSAcK Database
Capillipedium parviflorumKNApSAcK Database
Citrus reticulataKNApSAcK Database
Citrus sinensis L.KNApSAcK Database
Foeniculum vulgareKNApSAcK Database
Mandragora autumnalisKNApSAcK Database
Medicago sativaKNApSAcK Database
Ophrys fuscaKNApSAcK Database
Ophrys luteaKNApSAcK Database
Panax quinquefoliumKNApSAcK Database
Prunus aviumKNApSAcK Database
Rhodiola rosea L.KNApSAcK Database
Santalum albumKNApSAcK Database
Saposhnikovia divaricataKNApSAcK Database
Thymus eriocalyxKNApSAcK Database
Thymus X-porlockKNApSAcK Database
Tipuana tipuKNApSAcK Database
Species Where Detected
Species NameSourceReference
Lentinus edodes Sing.KNApSAcK Database
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
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-15.5 °Chttps://en.wikipedia.org/wiki/1-Octanol
Boiling Point195 °Chttps://en.wikipedia.org/wiki/1-Octanol
Water Solubility0.54 mg/mLhttps://en.wikipedia.org/wiki/1-Octanol
LogP3.00HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.53 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity40.54 m³·mol⁻¹ChemAxon
Polarizability17.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDHMDB0001183
DrugBank IDDB12452
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012583
KNApSAcK IDC00001264
Chemspider ID932
KEGG Compound IDC00756
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOctanol
METLIN ID6063
PubChem Compound957
PDB IDNot Available
ChEBI ID16188
Good Scents IDrw1021071
References
General References
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  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 ]