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Chemical Compound Review

Dodecanol     dodecan-1-ol

Synonyms: Lorol, Pisol, Dodecylalcohol, n-Dodecanol, Dodecanol-1, ...
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Disease relevance of Dodecanol


High impact information on Dodecanol


Chemical compound and disease context of Dodecanol

  • The most active compound is 1-dodecanol, followed by 1,2-dodecanediol and the C10 benzylidene acetal, which show 50% hemolysis at 15, 99 and 151 microM, respectively, at 37 degrees C. A few lysolecithins and longer chain cis-unsaturated alcohols were studied for comparison purposes, and were found to be more active than 1-dodecanol [10].

Biological context of Dodecanol

  • The crosslinked crystals were then used to catalyze the esterification of (R,S)-ibuprofen with dodecanol in octane at various water activities [11].
  • Azone and lauryl alcohol, a possible decomposition product of DDAIP, were used as standard enhancers for comparison [12].
  • Frog liver microsomes catalyzed the hydroxylation of 1-dodecanol into the corresponding omega- and (omega-1)-hydroxy derivatives [13].
  • It was concluded that the percutaneous absorption of DDA from microemulsions was enhanced with increasing the lauryl alcohol and water contents, and with decreasing the Labrasol:ethanol mixing ratio in the formulation [14].
  • No significative difference between LD50 was found when 1-dodecanol was injected in recently hatched adult R. prolixus (1-4 h old) nor in older adults (24 h old) [15].

Anatomical context of Dodecanol

  • 1. The effects of n-alcohols (ethanol to dodecanol) and anaesthetics on strychnine-sensitive glycine receptors were studied in Xenopus oocytes expressing homomeric alpha 1 or alpha 2 glycine receptor subunits, with the two electrode voltage-clamp recording technique [16].
  • Omega- and (omega-1)-hydroxylation of 1-dodecanol by frog liver microsomes [13].
  • The effective resistance of the intestinal unstirred water layer was measured with lauryl alcohol, and in control rats this resistance was lowest in the ileum, highest in the colon, and of intermediate value in the jejunum [17].
  • The results on partitioning coefficients in the n-octanol/buffer system were confirmed using an in vitro transport model with artificial (dodecanol collodium membrane) and biological membranes (Charles-River guinea pig) [18].
  • Analyzing lungs and trachea for the dodecyl alcohol indicated 25.6 micrograms/g, 27.1 microbrams/g, and 23.1 micrograms/g for rats caged individually, in threes, or in sevens, respectively [19].

Associations of Dodecanol with other chemical compounds


Gene context of Dodecanol

  • Dodecanol-tolerant strains were prepared from the wild type strain H222 as well as the acyl-CoA oxidase deleted (deltaPOX2, POX3, POX5) strain MTLY35 [25].
  • Dodecyl alcohol modified HAP exhibited a larger TGA mass loss upon heating (up to 4.8%) compared to untreated HAP (2.5-3.2wt%) [21].
  • 0. The formation of omega-hydroxydodecanol was more sharply inhibited by CO than was the formation of (omega-1)-hydroxydodecanol, implying that more than one cytochrome P-450 was involved in the hydroxylation of 1-dodecanol and that CO has a higher affinity for the P-450 catalyzing the omega-hydroxylation [13].
  • Surface modification of hydroxyapatite. Part I. Dodecyl alcohol [21].
  • SDS synthesis is a relatively simple process involving the sulfation of 1-dodecanol followed by neutralization with a cation source [26].

Analytical, diagnostic and therapeutic context of Dodecanol


  1. Effect of monolauryl succinate, lauryl alcohol and succinic acid on hemolysis and liver mitochondrial lysis in vitro in chicks. Ikumo, H. J. Nutr. (1980) [Pubmed]
  2. Production of the long-chain alcohols octanol, decanol, and dodecanol by Escherichia coli. Hamilton-Kemp, T., Newman, M., Collins, R., Elgaali, H., Yu, K., Archbold, D. Curr. Microbiol. (2005) [Pubmed]
  3. Skin permeation enhancement effect and skin irritation of saturated fatty alcohols. Kanikkannan, N., Singh, M. International journal of pharmaceutics. (2002) [Pubmed]
  4. Comparison of long-chain alcohols and other volatile compounds emitted from food-borne and related Gram positive and Gram negative bacteria. Elgaali, H., Hamilton-Kemp, T.R., Newman, M.C., Collins, R.W., Yu, K., Archbold, D.D. J. Basic Microbiol. (2002) [Pubmed]
  5. Nonanesthetic alcohols dissolve in synaptic membranes without perturbing their lipids. Miller, K.W., Firestone, L.L., Alifimoff, J.K., Streicher, P. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  6. Novel antagonists of alcohol inhibition of l1-mediated cell adhesion: multiple mechanisms of action. Wilkemeyer, M.F., Menkari, C.E., Charness, M.E. Mol. Pharmacol. (2002) [Pubmed]
  7. Macroporous polyacrylamide-based monolithic column with immobilized pH gradient for protein analysis. Zhu, G., Yuan, H., Zhao, P., Zhang, L., Liang, Z., Zhang, W., Zhang, Y. Electrophoresis (2006) [Pubmed]
  8. Interaction of Photobacterium leiognathi and Vibrio fischeri Y1 luciferases with fluorescent (antenna) proteins: bioluminescence effects of the aliphatic additive. Petushkov, V.N., Ketelaars, M., Gibson, B.G., Lee, J. Biochemistry (1996) [Pubmed]
  9. Expression of alkane hydroxylase from Acinetobacter sp. Strain ADP1 is induced by a broad range of n-alkanes and requires the transcriptional activator AlkR. Ratajczak, A., Geissdörfer, W., Hillen, W. J. Bacteriol. (1998) [Pubmed]
  10. Hemolysis of erythrocytes and fluorescence polarization changes elicited by peptide toxins, aliphatic alcohols, related glycols and benzylidene derivatives. Osorio e Castro, V.R., Ashwood, E.R., Wood, S.G., Vernon, L.P. Biochim. Biophys. Acta (1990) [Pubmed]
  11. Influence of water activity on the enantioselective esterification of (R,S)-ibuprofen by crosslinked crystals of Candida antarctica lipase B in organic solvent media. Pepin, P., Lortie, R. Biotechnol. Bioeng. (2001) [Pubmed]
  12. Synthesis and enhancing effect of dodecyl 2-(N,N-dimethylamino)propionate on the transepidermal delivery of indomethacin, clonidine, and hydrocortisone. Büyüktimkin, S., Büyüktimkin, N., Rytting, J.H. Pharm. Res. (1993) [Pubmed]
  13. Omega- and (omega-1)-hydroxylation of 1-dodecanol by frog liver microsomes. Miura, Y. Lipids (1981) [Pubmed]
  14. Transdermal delivery of diclofenac using microemulsions. Kweon, J.H., Chi, S.C., Park, E.S. Arch. Pharm. Res. (2004) [Pubmed]
  15. Biological effect of 1-dodecanol in teneral and post-teneral Rhodnius prolixus and Triatoma infestans (Hemiptera: Reduviidae). Cueto, G.M., Zerba, E., Picollo, M.I. Mem. Inst. Oswaldo Cruz (2005) [Pubmed]
  16. Enhancement of homomeric glycine receptor function by long-chain alcohols and anaesthetics. Mascia, M.P., Machu, T.K., Harris, R.A. Br. J. Pharmacol. (1996) [Pubmed]
  17. Effect of external abdominal irradiation on the dimensions and characteristics of the barriers to passive transport in the rat intestine. Thomson, A.B., Cheeseman, C.I., Walker, K. Lipids (1984) [Pubmed]
  18. Improvement of lipophilicity and membrane transport of cefuroxime using in vitro models. Mrestani, Y., Mrestani-Klaus, C., Bretschneider, B., Neubert, R.H. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft für Pharmazeutische Verfahrenstechnik e.V. (2004) [Pubmed]
  19. Pulmonary deposition of aerosols in individual and group caged rats. Ulrich, C.E., Marold, B.W. American Industrial Hygiene Association journal. (1979) [Pubmed]
  20. Mixtures of sodium dodecyl sulfate/dodecanol at the air/water interface by computer simulations. Domínguez, H., Rivera, M. Langmuir : the ACS journal of surfaces and colloids. (2005) [Pubmed]
  21. Surface modification of hydroxyapatite. Part I. Dodecyl alcohol. Borum-Nicholas, L., Wilson, O.C. Biomaterials (2003) [Pubmed]
  22. Functional diversity of cytochrome P450s of the white-rot fungus Phanerochaete chrysosporium. Matsuzaki, F., Wariishi, H. Biochem. Biophys. Res. Commun. (2004) [Pubmed]
  23. Antisense properties of end-modified oligonucleotides targeted to Ha-ras oncogene. Saison-Behmoaras, T.E., Duroux, I., Nguyen, T.T., Asseline, U., Hélène, C. Antisense Nucleic Acid Drug Dev. (1997) [Pubmed]
  24. Inclusion complexes of V-amylose with undecanoic acid and dodecanol at atomic resolution: X-ray structures with cycloamylose containing 26 D-glucoses (cyclohexaicosaose) as host. Nimz, O., Gessler, K., Usón, I., Sheldrick, G.M., Saenger, W. Carbohydr. Res. (2004) [Pubmed]
  25. Preparation of dodecanol-tolerant strains of Yarrowia lipolytica. Smit, M.S., Mokgoro, M.M., Setati, E., Nicaud, J.M. Biotechnol. Lett. (2004) [Pubmed]
  26. Fate and effects of the surfactant sodium dodecyl sulfate. Singer, M.M., Tjeerdema, R.S. Reviews of environmental contamination and toxicology. (1993) [Pubmed]
  27. Adsorption and surface rheology of n-dodecanol at the water/air interface. Ferrari, M., Ravera, F., Liggieri, L., Motschmann, H., Yi, Z., Krägel, J., Miller, R. Journal of colloid and interface science. (2004) [Pubmed]
  28. A new C12 alcohol identified as a sex pheromone and a trail-following pheromone in termites: the diene (Z,Z)-dodeca-3,6-dien-1-ol. Robert, A., Peppuy, A., Sémon, E., Boyer, F.D., Lacey, M.J., Bordereau, C. Naturwissenschaften (2004) [Pubmed]
  29. Optimization of HPLC chromatographic conditions for determination of Transkarbam 12 and its degradation products. Pasáková, I., Klimes, J., Sochor, J., Hrabálek, A. Journal of pharmaceutical and biomedical analysis. (2006) [Pubmed]
  30. Evaluation of the interaction of surfactants with stratum corneum model membrane from Bothrops jararaca by DSC. Baby, A.R., Lacerda, A.C., Velasco, M.V., Lopes, P.S., Kawano, Y., Kaneko, T.M. International journal of pharmaceutics. (2006) [Pubmed]
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