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Chemical Compound Review

hexadecan     hexadecane

Synonyms: HEXADECANE, n-Cetane, n-Hexadecane, H6703_ALDRICH, CHEMBL134994, ...
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Disease relevance of hexadecane


High impact information on hexadecane

  • Molecular dynamics simulations of a lipid bilayer and of hexadecane: an investigation of membrane fluidity [6].
  • Some partitioning processes, particularly involving polymeric solvents such as octanol or hexadecane, are governed not only by translational entropies and contact interactions, but also by free energies resulting from changes in the conformations of the polymer chains upon solute insertion [7].
  • Taken together with data on the incorporation of 18O2-derived oxygen into the hexadecane oxidation products, the present study demonstrates that a single P450 form is able to efficiently catalyze a cascade of sequential mono- and diterminal monooxygenation reactions from n-alkanes to alpha, omega-dioic acids with high regioselectivity [8].
  • Besides the primary product, 1-hexadecanol, the conversion of hexadecane yielded up to five additional metabolites, which were identified by gas chromatography-electron impact mass spectrometry as hexadecanal, hexadecanoic acid, 1, 16-hexadecanediol, 16-hydroxyhexadecanoic acid, and 1, 16-hexadecanedioic acid [8].
  • The highly purified delta(1-66)P450Cm1 exhibited unchanged spectral characteristics and catalyzed the hydroxylation of n-hexadecane with 85% of the activity determined for full-length wild-type P450Cm1 [9].

Chemical compound and disease context of hexadecane


Biological context of hexadecane

  • In previous studies, the rates of epidermal glycolysis and amino acid incorporation were found to parallel rates of mitosis in both the hypoplasia associated with starvation and the hyperplasia produced by treatment with hexadecane [3].
  • The gel-like phases obtained in hexadecane, toluene and chloroform have been investigated by optical microscopy and small-angle X-ray diffraction: the type of phase observed is related to the molecular structure of the compounds and depends dramatically on the solvent [15].
  • Shifting zero- to first-order (first-order) desulfurization rate kinetics were observed when MD 1850 was diluted with hexadecane [16].
  • The effects of DOT reduction on the amount and rate of hexadecane degraded and on the degree of mineralization and on the production of biomass were investigated [17].
  • A method, based on quantitating 14CO2 produced from [14C]hexadecane, has been developed for estimating the rate of hexadecane decomposition in seawater of Tokyo Bay during the summer stagnation period [18].

Anatomical context of hexadecane

  • The results of experiments on the adhesion of glutaraldehyde-fixed red blood cells to both polarizable metal/saline and liquid hexadecane/saline interfaces have been analysed in terms of physical forces [19].
  • To study some of the biochemical and physical states of membranes associated with hyperproliferation, the effect of topical hexadecane on membrane fluidity in guinea pig epidermis was investigated by electron spin resonance using a 5-doxylstearic acid spin labeling agent [20].
  • The cell surfaces of a range of variants of Streptococcus salivarius HB, altered in cell wall antigen composition, were compared with those of the parent with respect to adherence, ability to adsorb to hexadecane, morphology, and exposure of lipoteichoic acid (LTA) [21].
  • Band 1 of hexadecane-grown cells had a ratio of lipid phosphorus to protein that was almost twice that of cytoplasmic membrane and a correspondingly low buoyant density (1.086 g/cm3) [22].
  • Similar microbodies were also observed in cells of R. glutinis CY grown on hexadecane [23].

Associations of hexadecane with other chemical compounds


Gene context of hexadecane

  • CYP86A1 was found to catalyze the omega-hydroxylation of saturated and unsaturated fatty acids with chain lengths from C12 to C18 but not of hexadecane [29].
  • In order to examine metabolic profiles of 4-n-NP in the NT, CYP1A1 and CYP1A2 cultures, the suspensions were exposed to 10 mg 1(-1) of 14C-4-n-NP using a two-liquid-phase system with carrier n-hexadecane and 192 h of incubation [30].
  • Disruption of the rubredoxin-encoding gene by insertion of a KmR/lacZ cassette rendered the resulting strain unable to grow on dodecane or hexadecane [31].
  • Emulsions that were stable even after heating or freezing resulted when equal volumes of hexadecane and a 70:30 blend of Tween 80/Span 80(T80/S80) were mixed and then diluted with normal saline solution to the desired hexadecane concentration [32].
  • Epdlp could be involved in cell wall maintenance and is essential for pseudohyphal growth induced by CEN and n-hexadecane at pH 4 and by n-hexadecane at pH 7.) In this paper, we cloned EPD2 of C. maltosa, which is highly similar to EPD1, PHR1, and PHR2 [33].

Analytical, diagnostic and therapeutic context of hexadecane


  1. Interstitial and hemorrhagic pneumonitis induced by mycobacterial trehalose dimycolate. Seggev, J., Goren, M.B., Carr, R.I., Kirkpatrick, C.H. Am. J. Pathol. (1982) [Pubmed]
  2. Characterization of the extracellular lipase, LipA, of Acinetobacter calcoaceticus BD413 and sequence analysis of the cloned structural gene. Kok, R.G., van Thor, J.J., Nugteren-Roodzant, I.M., Brouwer, M.B., Egmond, M.R., Nudel, C.B., Vosman, B., Hellingwerf, K.J. Mol. Microbiol. (1995) [Pubmed]
  3. The diurnal variation of epidermal metabolism. Harris, R.R., Mackenzie, I.C. J. Invest. Dermatol. (1982) [Pubmed]
  4. Adherence of Acinetobacter calcoaceticus RAG-1 to human epithelial cells and to hexadecane. Rosenberg, M., Perry, A., Bayer, E.A., Gutnick, D.L., Rosenberg, E., Ofek, I. Infect. Immun. (1981) [Pubmed]
  5. Inhibition of the interaction of Streptococcus sanguis with hexadecane droplets by 55- and 60-kilodalton hydrophobic proteins of human saliva. Babu, J.P., Beachey, E.H., Simpson, W.A. Infect. Immun. (1986) [Pubmed]
  6. Molecular dynamics simulations of a lipid bilayer and of hexadecane: an investigation of membrane fluidity. Venable, R.M., Zhang, Y., Hardy, B.J., Pastor, R.W. Science (1993) [Pubmed]
  7. Solvation: how to obtain microscopic energies from partitioning and solvation experiments. Chan, H.S., Dill, K.A. Annual review of biophysics and biomolecular structure. (1997) [Pubmed]
  8. Oxygenation cascade in conversion of n-alkanes to alpha,omega-dioic acids catalyzed by cytochrome P450 52A3. Scheller, U., Zimmer, T., Becher, D., Schauer, F., Schunck, W.H. J. Biol. Chem. (1998) [Pubmed]
  9. Generation of the soluble and functional cytosolic domain of microsomal cytochrome P450 52A3. Scheller, U., Kraft, R., Schröder, K.L., Schunck, W.H. J. Biol. Chem. (1994) [Pubmed]
  10. Berberine sulfate blocks adherence of Streptococcus pyogenes to epithelial cells, fibronectin, and hexadecane. Sun, D., Courtney, H.S., Beachey, E.H. Antimicrob. Agents Chemother. (1988) [Pubmed]
  11. An examination of the relationship between experimentally altered rates of epidermal proliferations and rates of epidermal metabolism assayed in vitro. Harris, R.R., Mackenzie, I.C., Williams, R.A. J. Invest. Dermatol. (1980) [Pubmed]
  12. Alcohol dehydrogenases in Acinetobacter sp. strain HO1-N: role in hexadecane and hexadecanol metabolism. Singer, M.E., Finnerty, W.R. J. Bacteriol. (1985) [Pubmed]
  13. Mechanism of enhancement of microbial cell hydrophobicity by cationic polymers. Goldberg, S., Doyle, R.J., Rosenberg, M. J. Bacteriol. (1990) [Pubmed]
  14. Stable isotope incorporation triples the upper mass limit for determination of elemental composition by accurate mass measurement. Rodgers, R.P., Blumer, E.N., Hendrickson, C.L., Marshall, A.G. J. Am. Soc. Mass Spectrom. (2000) [Pubmed]
  15. Gel-like lyomesophases formed in organic solvents by self-assembled guanine ribbons. Giorgi, T., Grepioni, F., Manet, I., Mariani, P., Masiero, S., Mezzina, E., Pieraccini, S., Saturni, L., Spada, G.P., Gottarelli, G. Chemistry (Weinheim an der Bergstrasse, Germany) (2002) [Pubmed]
  16. Microbial desulfurization of alkylated dibenzothiophenes from a hydrodesulfurized middle distillate by Rhodococcus erythropolis I-19. Folsom, B.R., Schieche, D.R., DiGrazia, P.M., Werner, J., Palmer, S. Appl. Environ. Microbiol. (1999) [Pubmed]
  17. Hexadecane mineralization in oxygen-controlled sediment-seawater cultivations with autochthonous microorganisms. Michaelsen, M., Hulsch, R., Höpner, T., Berthe-Corti, L. Appl. Environ. Microbiol. (1992) [Pubmed]
  18. Method for estimating the decomposition of hexadecane in the marine environment. Seki, H. Appl. Environ. Microbiol. (1976) [Pubmed]
  19. Red blood cell adhesion. III. Analysis of forces. Parsegian, V.A., Gingell, D. J. Cell. Sci. (1980) [Pubmed]
  20. Changes of electron spin resonance membrane fluidity in hexadecane-induced hyperproliferative epidermis. Tanaka, T., Ogura, R., Hidaka, T., Sugiyama, M. J. Invest. Dermatol. (1989) [Pubmed]
  21. Relationship of cell surface morphology and composition of Streptococcus salivarius K+ to adherence and hydrophobicity. Weerkamp, A.H., van der Mei, H.C., Slot, J.W. Infect. Immun. (1987) [Pubmed]
  22. Isolation and characterization of membranes from a hydrocarbon-oxidizing Acinetobacter sp. Scott, C.C., Makula, S.R., Finnerty, W.R. J. Bacteriol. (1976) [Pubmed]
  23. Ultrastructure of methanotrophic yeasts. Wolf, H.J., Christiansen, M., Hanson, R.S. J. Bacteriol. (1980) [Pubmed]
  24. Pressure-induced lock-in in an aperiodic nanoporous crystal. Toudic, B., Aubert, F., Ecolivet, C., Bourges, P., Breczewski, T. Phys. Rev. Lett. (2006) [Pubmed]
  25. Adhesion of red blood cells to charged interfaces between immiscible liquids. A new method. Gingell, D., Todd, I. J. Cell. Sci. (1975) [Pubmed]
  26. Hydrophobic interactions and the adherence of Streptococcus sanguis to hydroxylapatite. Nesbitt, W.E., Doyle, R.J., Taylor, K.G. Infect. Immun. (1982) [Pubmed]
  27. A study of the enthalpy and entropy contributions of the stationary phase in reversed-phase liquid chromatography. Ranatunga, R.P., Carr, P.W. Anal. Chem. (2000) [Pubmed]
  28. Penetration of benzene through human skin. Blank, I.H., McAuliffe, D.J. J. Invest. Dermatol. (1985) [Pubmed]
  29. CYP86A1 from Arabidopsis thaliana encodes a cytochrome P450-dependent fatty acid omega-hydroxylase. Benveniste, I., Tijet, N., Adas, F., Philipps, G., Salaün, J.P., Durst, F. Biochem. Biophys. Res. Commun. (1998) [Pubmed]
  30. Metabolism of 4-n-nonylphenol by non-modified and CYP1A1- and CYP1A2-transgenic cell cultures of tobacco. Berger, A., S Russ, A., Schuphan, I., Schmidt, B. Z. Naturforsch., C, J. Biosci. (2005) [Pubmed]
  31. Two genes encoding proteins with similarities to rubredoxin and rubredoxin reductase are required for conversion of dodecane to lauric acid in Acinetobacter calcoaceticus ADP1. Geissdörfer, W., Frosch, S.C., Haspel, G., Ehrt, S., Hillen, W. Microbiology (Reading, Engl.) (1995) [Pubmed]
  32. Stable oil-in-water emulsions: preparation and use as vaccine vehicles for lipophilic adjuvants. Woodard, L.F., Jasman, R.L. Vaccine (1985) [Pubmed]
  33. Cloning and characterization of EPD2, a gene required for efficient pseudohyphal formation of a dimorphic yeast, Candida maltosa. Nakazawa, T., Takahashi, M., Horiuchi, H., Ohta, A., Takagi, M. Biosci. Biotechnol. Biochem. (2000) [Pubmed]
  34. Observation of the transient rotator phase of n-hexadecane in emulsified droplets with time-resolved two-dimensional small- and wide-angle X-ray scattering. Shinohara, Y., Kawasaki, N., Ueno, S., Kobayashi, I., Nakajima, M., Amemiya, Y. Phys. Rev. Lett. (2005) [Pubmed]
  35. Synthesis and use of the n-bromododecane-1,12-diols as conformational probes for general anesthetic target sites. Dickinson, R., Smith, E.H., Franks, N.P., Lieb, W.R. J. Med. Chem. (1993) [Pubmed]
  36. Assessing the role of Pseudomonas aeruginosa surface-active gene expression in hexadecane biodegradation in sand. Holden, P.A., LaMontagne, M.G., Bruce, A.K., Miller, W.G., Lindow, S.E. Appl. Environ. Microbiol. (2002) [Pubmed]
  37. Destruction of the outer membrane permeability barrier of Escherichia coli by heat treatment. Tsuchido, T., Katsui, N., Takeuchi, A., Takano, M., Shibasaki, I. Appl. Environ. Microbiol. (1985) [Pubmed]
  38. Characterization of intracytoplasmic hydrocarbon inclusions from the hydrocarbon-oxidizing Acinetobacter species HO1-N. Scott, C.C., Finnerty, W.R. J. Bacteriol. (1976) [Pubmed]
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