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Chemical Compound Review

DODECANE     dodecane

Synonyms: Bihexyl, Dihexyl, Dodekan, dodecan, N-Dodecan, ...
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Disease relevance of dodecane

  • In comparison with TPA, both mezerein and n-dodecane at promoting doses induced less sustained hyperplasia in SENCAR mouse skin, a finding also consistent with the proposal that n-dodecane is principally active in stage II of two-stage promotion models [1].
  • Compared to the potent phorbol diester 12-O-tetradecanoylphorbol-13-acetate (TPA), n-dodecane was several orders of magnitude less potent on a dose basis, and maximal papilloma response required more extended application (22 weeks for 50 mg dodecane compared to 12 weeks for 2 micrograms TPA) [1].
  • Enhanced degradation and toxicity reduction of dihexyl phthalate by Fusarium oxysporum f. sp. pisi cutinase [2].
  • The primary biodegradation of dihexyl sulfosuccinate has been demonstrated using two single cultures and three mixed bacterial cultures of Comamonas terrigena [3].

High impact information on dodecane

  • Observation of the size distribution of transient cavities in computer simulations of water, n-hexane, and n-dodecane under benchtop conditions shows that the sizes of cavities are more sharply defined in liquid water but the most-probable-size cavities are about the same size in each of these liquids [4].
  • Mezerein differed from both TPA and n-dodecane in inducing a significant increase only in eosinophils [5].
  • In contrast, marked increases were predictably observed with TPA and mezerein, maximal responses occurring after 48-72 h. n-Dodecane induced no increase in the number of keratinocytes with dense cytoplasm and increased affinity for basophilic dyes (dark cells), only TPA demonstrating this activity [6].
  • Front-surface fluorescence spectroscopy was used to evidence differences in the structure of bovine serum albumin (BSA) adsorbed at the interface of emulsions prepared with different apolar phases: an hydrocarbon (n-dodecane), a synthetic medium-chain triglyceride (miglyol) and a natural vegetable oil (sunflower oil) [7].
  • These systems are highly responsive to hydrocarbons: the addition of n-heptane or n-dodecane reduces the viscosity of solutions by up to 4 to 5 orders of magnitude, thus inducing the transition of a gellike system to a fluid one [8].

Biological context of dodecane


Associations of dodecane with other chemical compounds

  • A similar phenomenon was observed with n-dodecane and EPP, with an additional increase in eosinophils which was not observed with TPA [5].
  • The degenerate electron exchange (DEE) reaction involving radical cations (RCs) of n-nonane, n-dodecane, and n-hexadecane in n-hexane solution was studied over the temperature range 253-313 K using the method of time-resolved magnetic field effect in recombination fluorescence of spin-correlated radical ion pairs [12].
  • Spherical micelles of a polystyrene-b-poly(dimethylsiloxane) (PS-b-PDMS) diblock copolymer with the number-average molecular weight of 193 000 g/mol for PS and 39 000 g/mol for PDMS were obtained by using n-dodecane or n-octane as the selective solvent for the PDMS block [13].
  • The drug was capable of hydrogen bonding with silanol groups in the n-dodecane gels, which increase gel strength at low concentrations; at high concentrations, the drug acted as a plasticizer [14].
  • Using the PS/P(DMA-stat-EGDMA) latex particles as a pH-responsive particulate ('Pickering'-type) emulsifier, polydisperse n-dodecane-in-water emulsions were prepared at pH 8 that could be partially broken (demulsified) on lowering the solution pH to 3 [15].

Gene context of dodecane

  • Cell diameters were increased by an increase in acyl chain length and saturation, and was affected by additives such an n-dodecane and acyl2Gro [16].
  • The effect of solvent polarity and lipophilicity on DNA adduct formation by polycyclic aromatic hydrocarbons in skin and lung has been studied in CD1 mice exposed cutaneously in vivo to benzo(a)pyrene ( approximately 0.01-7.0 microg/animal) in either tetrahydrofuran or n-dodecane [10].

Analytical, diagnostic and therapeutic context of dodecane

  • After four applications of n-dodecane the number of epidermal cell layers and mitotic index were equal to or greater than those observed with TPA [6].
  • The magnitude of the positive effect of n-dodecane depends both on the broths' characteristics and operational conditions of the bioreactor [17].


  1. Mechanism of mouse skin tumor promotion by n-dodecane. Baxter, C.S., Miller, M.L. Carcinogenesis (1987) [Pubmed]
  2. Enhanced degradation and toxicity reduction of dihexyl phthalate by Fusarium oxysporum f. sp. pisi cutinase. Kim, Y.H., Seo, H.S., Min, J., Kim, Y.C., Ban, Y.H., Han, K.Y., Park, J.S., Bae, K.D., Gu, M.B., Lee, J. J. Appl. Microbiol. (2007) [Pubmed]
  3. Dihexyl sulfosuccinate biodegradation by mixed cultures. Chmelárová, Z., Závadská, I., Húska, J., Tóth, D. Folia Microbiol. (Praha) (2000) [Pubmed]
  4. Theory of hydrophobicity: transient cavities in molecular liquids. Pratt, L.R., Pohorille, A. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  5. Comparative histomorphometric changes in SENCAR mouse epidermis in response to multiple treatments with complete and stage-specific tumor promoting agents. Baxter, C.S., Andringa, A., Chalfin, K., Miller, M.L. Carcinogenesis (1989) [Pubmed]
  6. Critical comparison of histological and morphometric changes in SENCAR mouse epidermis in response to n-dodecane, 12-O-tetradecanoylphorbol-13-acetate and mezerein. Miller, M.L., Andringa, A., Baxter, C.S. Carcinogenesis (1988) [Pubmed]
  7. The nature of the apolar phase influences the structure of the protein emulsifier in oil-in-water emulsions stabilized by bovine serum albumin. A front-surface fluorescence study. Rampon, V., Brossard, C., Mouhous-Riou, N., Bousseau, B., Llamas, G., Genot, C. Advances in colloid and interface science. (2004) [Pubmed]
  8. Self-assembled networks highly responsive to hydrocarbons. Molchanov, V.S., Philippova, O.E., Khokhlov, A.R., Kovalev, Y.A., Kuklin, A.I. Langmuir : the ACS journal of surfaces and colloids (2007) [Pubmed]
  9. The pharmacokinetics of benzo[alpha]pyrene in the isolated perfused rabbit lung: the influence of benzo[alpha]pyrene, n-dodecane, particulate, or sulfur dioxide. Morgan, D.D., Warshawsky, D., Niemeier, R.W., Bingham, E. Toxicology (1984) [Pubmed]
  10. Effects of solvent on DNA adduct formation in skin and lung of CD1 mice exposed cutaneously to benzo(a)pyrene. Booth, E.D., Loose, R.W., Watson, W.P. Arch. Toxicol. (1999) [Pubmed]
  11. Effect of starvation and chloramphenicol on acceleration of bacterial dihexyl sulfosuccinate biotransformation. Chmelárová, Z., Závadská, I., Húska, J., Tóth, D. Folia Microbiol. (Praha) (2000) [Pubmed]
  12. Degenerate Electron Exchange Reaction of n-Alkane Radical Cations in Solution. Borovkov, V.I., Gritsan, N.P., Yeletskikh, I.V., Bagryansky, V.A., Molin, Y.N. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory (2006) [Pubmed]
  13. Crust effect on multiscale pattern formations in drying micelle solution drops on solid substrates. Ma, X., Xia, Y., Chen, E.Q., Mi, Y., Wang, X., Shi, A.C. Langmuir : the ACS journal of surfaces and colloids. (2004) [Pubmed]
  14. Rheological and drug release properties of oil gels containing colloidal silicon dioxide. Sherriff, M., Enever, R.P. Journal of pharmaceutical sciences. (1979) [Pubmed]
  15. Synthesis of polystyrene/poly[2-(dimethylamino)ethyl methacrylate-stat-ethylene glycol dimethacrylate] core-shell latex particles by seeded emulsion polymerization and their application as stimulus-responsive particulate emulsifiers for oil-in-water emulsions. Fujii, S., Randall, D.P., Armes, S.P. Langmuir : the ACS journal of surfaces and colloids. (2004) [Pubmed]
  16. Membrane lipid composition and cell size of Acholeplasma laidlawii strain A are strongly influenced by lipid acyl chain length. Wieslander, A., Nordström, S., Dahlqvist, A., Rilfors, L., Lindblom, G. Eur. J. Biochem. (1995) [Pubmed]
  17. Enhancement of oxygen mass transfer in stirred bioreactors using oxygen-vectors. 1. Simulated fermentation broths. Galaction, A.I., Cascaval, D., Oniscu, C., Turnea, M. Bioprocess and biosystems engineering. (2004) [Pubmed]
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