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Chemical Compound Review

n-hexyl     hexane

Synonyms: AC1L3B4F, 1-C6H13, 2679-29-0, 1-Hexyl radical, 5200-EP0930075A1, ...
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Disease relevance of hexane

  • The linear relation obtained using delta G degrees B,dh -delta G degrees B,w has the same slope, but the intercept is decreased to -1.48 +/- 0.19 kcal/mol, indicating that quinone binding strengths in the hexane system are uniformly enhanced after partial dehydration [1].
  • Capsid (CA) proteins in wt mature viruses possess cysteines near their carboxy termini at gag codons 330 and 350, but these residues are not involved in natural covalent intermolecular bonds, nor can they be intermolecularly cross-linked by using the membrane-permeable cross-linker bis-maleimido hexane [2].
  • We have synthesized as potential imaging agents for human breast tumors a series of hexestrol analogues bearing the halogens fluorine, chlorine, bromine, and iodine at the terminus of the hexane chain [3].
  • A remarkably increased enantioselectivity was obtained when the salt was added at 3-10 mol % versus substrate in the Burkholderia cepacia lipase (lipase PS-C)-catalyzed transesterification of 1-phenylethanol by using vinyl acetate in diisopropyl ether or a hexane solvent system [4].
  • The toxicity equivalency quantity (TEQ), which was measured by the HRGC-HRMS analysis, for the total residues of isomers was reduced from 22,000 to 210 pg TEQ/mL of hexane (conversion: 99.05%) at room temperature [5].

Psychiatry related information on hexane


High impact information on hexane


Chemical compound and disease context of hexane

  • When the E. coli cells displaying lipases were used for enantioselective resolution of racemic 1-phenylethanol in hexane, (R)-phenyl ethyl acetate was successfully obtained with the enantiomeric excess of greater than 96% in 36 h of reaction [11].
  • Fecal samples that were incubated under anaerobic conditions at 37 degrees C for 96 h or frozen without incubation, were extracted with hexane: peroxide-free diethyl ether (1:1), partially purified on a silica Sep-pak cartridge and assayed for mutagenicity using the Salmonella typhimurium/mammalian microsome system [12].
  • The hexane fraction inhibited the edema formation by 35.9% at a dose of 200 mg/kg (p.o.) but no activity was observed at 100 mg/kg (p.o.). The triterpenes present in the hexane fraction were identified as lupeol acetate, alpha-amyrin and lupeol cinnamates [13].
  • Furthermore, the hexane and methanol extracts, and the new compound were found to be moderately active against Mycobacterium tuberculosis [14].
  • Average weight gains to 6 wk of age were 13.8, 7.3, and 2.8 kg and mortality was 0/20, 4/20, and 9/20 for calves fed milk, ethanol-extracted soy, and hexane-extracted soy, respectively [15].

Biological context of hexane

  • The UV/vis spectrum of the silylene in anhydrous hexane at 25 degrees C, determined by laser flash photolysis methods, agrees well with that obtained in frozen hydrocarbon matrixes, and that of the dimerization product, tetraphenyldisilene, is tentatively assigned [16].
  • We have also characterized this activating component by using a hexane-extracted serum fraction to examine PPAR activator levels in normal and preeclamptic (PE) pregnancies [17].
  • The crystalline enzyme retains its active conformation in the nonpolar medium and can catalyze both hydrolysis and synthesis reactions in hexane [18].
  • Fractionating the residue from one of the sites by sequential extraction with organic solvents indicated that while the ability to produce both types of DNA damage was contained mostly in a hexane-soluble fraction, a benzene-soluble fraction produced high levels of reactive oxygens relative to the number of total DNA adducts [19].
  • After protein denaturation and addition of an internal standard, tocol, 250-microL samples are twice extracted with hexane [20].

Anatomical context of hexane

  • Spin-coating from hexane does not produce cellular structure, yet a strong correlation is retained in the positions of nanocrystal aggregates [21].
  • The lipophilic variant 11 has been employed for the enantioselective transport of N-acetylphenylalanine, a) through dichloromethane (DCM) and dichloroethane (DCE) bulk liquid membranes (U-tube apparatus), and b) through 2.5% (v/v) octanol/hexane via hollow fibre membrane contactors [22].
  • Phospholipid species containing long and very long polyenoic fatty acids remain with rhodopsin after hexane extraction of photoreceptor membranes [23].
  • We have tested the reproducibility of this method by serial measurements of sebum excretion rates (SER) of 10 individuals over a 6-week period, and in addition we have correlated this method with the conventional hexane extraction technique [24].
  • 5'-Nucleotidase purified from rat liver microsomes was subjected to BrCN cleavage, hexane extraction, and high-performance liquid chromatography, resulting in the purification of a single fragment with Mr 2300 [25].

Associations of hexane with other chemical compounds


Gene context of hexane

  • Doenjang hexane fraction-induced G1 arrest is associated with the inhibition of pRB phosphorylation and induction of Cdk inhibitor p21 in human breast carcinoma MCF-7 cells [30].
  • Hexane-soluble derivatives of okadaic acid (OA) and dinophysistoxin-2 (DTX-2) were found [31].
  • It is interesting to note that hexane, BuOH and EtOAc extracts (100 microg/ml) also inhibited the functional activation of beta1-integrins (CD29) assessed by U937 homotypic aggregation up to 70-80% [32].
  • The effect of fatty acid unsaturation on the antioxidant activity of beta-carotene and alpha-tocopherol in hexane solutions [33].
  • The free energies of activation for the reaction at 25 degrees C were reduced by 1.3-1.5 kcal/mol in the bilayer environment compared to that of hexane [34].

Analytical, diagnostic and therapeutic context of hexane

  • After extraction, analytes were desorbed in hexane and analyzed using gas chromatography/mass spectrometry [35].
  • The latter is washed with hexane, then subjected to reversed-phase liquid chromatography and ultraviolet detection at 202 nm [36].
  • After addition of 150 microliter of hexane, shaking and centrifugation, an aliquot of the upper phase was injected into the gas chromatograph [37].
  • The products, EtOQ0C10 and (ETO)2Q0C10, were separated by thin-layer chromatography using hexane/ether (3.5:1) as the developing solvent [38].
  • Microemulsion electrokinetic chromatography separation by using hexane-in-water microemulsions without cosurfactant: Comparison with MEKC [39].


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  13. Anti-inflammatory and analgesic activities of the latex containing triterpenes from Himatanthus sucuuba. de Miranda, A.L., Silva, J.R., Rezende, C.M., Neves, J.S., Parrini, S.C., Pinheiro, M.L., Cordeiro, M.C., Tamborini, E., Pinto, A.C. Planta Med. (2000) [Pubmed]
  14. Diterpenes from the berries of Juniperus excelsa. Topçu, G., Erenler, R., Cakmak, O., Johansson, C.B., Celik, C., Chai, H.B., Pezzuto, J.M. Phytochemistry (1999) [Pubmed]
  15. Causes of adverse responses to soybean milk replacers in young calves. Gardner, R.W., Shupe, M.G., Brimhall, W., Weber, D.J. J. Dairy Sci. (1990) [Pubmed]
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  17. Circulating activators of peroxisome proliferator-activated receptors are reduced in preeclamptic pregnancy. Waite, L.L., Louie, R.E., Taylor, R.N. J. Clin. Endocrinol. Metab. (2005) [Pubmed]
  18. X-ray crystal structure of gamma-chymotrypsin in hexane. Yennawar, N.H., Yennawar, H.P., Farber, G.K. Biochemistry (1994) [Pubmed]
  19. Coal tar residues produce both DNA adducts and oxidative DNA damage in human mammary epithelial cells. Leadon, S.A., Sumerel, J., Minton, T.A., Tischler, A. Carcinogenesis (1995) [Pubmed]
  20. Determination of retinol, alpha-tocopherol, and beta-carotene in serum by liquid chromatography with absorbance and electrochemical detection. MacCrehan, W.A., Schönberger, E. Clin. Chem. (1987) [Pubmed]
  21. Nanostructured cellular networks. Moriarty, P., Taylor, M.D., Brust, M. Phys. Rev. Lett. (2002) [Pubmed]
  22. Enantioselective transport by a steroidal guanidinium receptor. Baragaña, B., Blackburn, A.G., Breccia, P., Davis, A.P., de Mendoza, J., Padrón-Carrillo, J.M., Prados, P., Riedner, J., de Vries, J.G. Chemistry (Weinheim an der Bergstrasse, Germany) (2002) [Pubmed]
  23. Phospholipid species containing long and very long polyenoic fatty acids remain with rhodopsin after hexane extraction of photoreceptor membranes. Aveldaño, M.I. Biochemistry (1988) [Pubmed]
  24. Measurement of sebum output using a lipid absorbent tape. Nordstrom, K.M., Schmus, H.G., McGinley, K.J., Leyden, J.J. J. Invest. Dermatol. (1986) [Pubmed]
  25. Membrane-anchoring domain of rat liver 5'-nucleotidase: identification of the COOH-terminal serine-523 covalently attached with a glycolipid. Ogata, S., Hayashi, Y., Misumi, Y., Ikehara, Y. Biochemistry (1990) [Pubmed]
  26. Influence of media and homoconjugate pairing on transition metal hydride protonation. An IR and DFT study on proton transfer to CpRuH(CO)(PCy3). Belkova, N.V., Besora, M., Epstein, L.M., Lledós, A., Maseras, F., Shubina, E.S. J. Am. Chem. Soc. (2003) [Pubmed]
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  28. Computer simulation of the distribution of hexane in a lipid bilayer: spatially resolved free energy, entropy, and enthalpy profiles. MacCallum, J.L., Tieleman, D.P. J. Am. Chem. Soc. (2006) [Pubmed]
  29. Direct detection of dimethylstannylene and tetramethyldistannene in solution and the gas phase by laser flash photolysis of 1,1-dimethylstannacyclopent-3-enes. Becerra, R., Gaspar, P.P., Harrington, C.R., Leigh, W.J., Vargas-Baca, I., Walsh, R., Zhou, D. J. Am. Chem. Soc. (2005) [Pubmed]
  30. Doenjang hexane fraction-induced G1 arrest is associated with the inhibition of pRB phosphorylation and induction of Cdk inhibitor p21 in human breast carcinoma MCF-7 cells. Choi, Y.H., Choi, B.T., Lee, W.H., Rhee, S.H., Park, K.Y. Oncol. Rep. (2001) [Pubmed]
  31. Esters of okadaic acid and dinophysistoxin-2 in Portuguese bivalves related to human poisonings. Vale, P., Sampayo, M.A. Toxicon (1999) [Pubmed]
  32. In vitro anti-inflammatory and anti-oxidative effects of Cinnamomum camphora extracts. Lee, H.J., Hyun, E.A., Yoon, W.J., Kim, B.H., Rhee, M.H., Kang, H.K., Cho, J.Y., Yoo, E.S. Journal of ethnopharmacology. (2006) [Pubmed]
  33. The effect of fatty acid unsaturation on the antioxidant activity of beta-carotene and alpha-tocopherol in hexane solutions. Palozza, P., Luberto, C., Bartoli, G.M. Free Radic. Biol. Med. (1995) [Pubmed]
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