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Chemical Compound Review

Phytane     2,6,10,14- tetramethylhexadecane

Synonyms: Phytan, CHEBI:48937, AC1L1ZRX, CTK5B9971, LMPR0104010019, ...
 
 
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Disease relevance of Phytan

  • Alcanivorax borkumensis strain ST-T1 isolated from the Sea of Japan exhibited higher ability to degrade branched alkanes (pristane and phytane) than A. venetianus strain T4 [1].
  • A new isolate, Mycobacterium sp. strain P101, is capable of growth on methyl-branched alkanes (pristane, phytane, and squalane) [2].
  • The most extensively studied model of plasmacytomagenesis is the induction of plasmacytomas in BALB/c mice by i.p. injections of mineral oil or, chemically more defined, by several branched alkanes such as pristane (2.6.10.14-tetramethylpentadecane), phytane (2.6.10.14-tetramethylhexadecane), and 7-n-hexyloctadecane [3].
 

High impact information on Phytan

  • The hydrocarbon composition of the seep soils consisted almost entirely of saturated, acyclic alkanes (e.g., n-alkanes with chain lengths of C15 to C30, as well as branched alkanes, predominately pristane and phytane) [4].
  • The isoprenoid hydrocarbon, trans-phyt-2-ene (82.2%), phyt-1-ene (6.5%), and phytane (11.3%), were detected in bovine rumen liquor by means of AgNO3-impregnated thin layer chromatography and gas liquid chromatography with mass spectrometry and infrared spectrophotometry [5].
  • The concentrations of TPH and UCM in sediments declined to around 40 microg g(-1), pristane and phytane dropped by 80%, and the ratio of light to total n-alkanes was 0.15, suggesting that residual oil in sediments was weathered leading to a remarkable recovery of the unhealthy saplings [6].
  • Using the 17alpha,21beta-C30-hopane as an internal inert reference, we could demonstrate that, after 12 months of in situ incubation, 55% of the losses of the n-alkanes < or = C25 and 35% of the losses of the heavier n-alkanes and of Pr and Ph were due to biodegradation processes [7].
  • The presence of phytane and UCM (> 3) together to PR/C17 and PH/C18 ratios (both < 1) suggest a large contribution of crude oils [8].
 

Associations of Phytan with other chemical compounds

  • The molecular markers for these emissions include the high molecular weight PAHs, the n-alkanes, a Carbon Preference Index approximately 1 (odd carbon:even carbon approximately 1), as well as pristane and phytane as specific markers for fuel oil degradation [9].
 

Gene context of Phytan

  • The concentrations including n-alkanes from C13 to C36, pristane and phytane were in the range of 0.60 to 170.10 microg/g, with a median value of 4.26 [10].
 

Analytical, diagnostic and therapeutic context of Phytan

  • GC-MS analyses of hydrolyzed total lipid extracts revealed that the co-culture of N. equitans and Ignicoccus sp. strain KIN4/I, as well as Ignicoccus sp. strain KIN4/I grown at 90 degrees C, contained phytane and biphytane in a ratio of approximately 4:1 [11].

References

  1. Alcanivorax which prevails in oil-contaminated seawater exhibits broad substrate specificity for alkane degradation. Hara, A., Syutsubo, K., Harayama, S. Environ. Microbiol. (2003) [Pubmed]
  2. Role of alpha-methylacyl coenzyme A racemase in the degradation of methyl-branched alkanes by Mycobacterium sp. strain P101. Sakai, Y., Takahashi, H., Wakasa, Y., Kotani, T., Yurimoto, H., Miyachi, N., Van Veldhoven, P.P., Kato, N. J. Bacteriol. (2004) [Pubmed]
  3. Genotoxicity assessment of the plasmacytomagenic agent pristane (2.6.10.14-tetramethylpentadecane) and four related alkanes by the SOS chromotest. Janz, S., Huttunen, T., Herzschuh, R., Storch, H. Arch. Geschwulstforsch. (1988) [Pubmed]
  4. Diversity and functional analysis of bacterial communities associated with natural hydrocarbon seeps in acidic soils at Rainbow Springs, Yellowstone National Park. Hamamura, N., Olson, S.H., Ward, D.M., Inskeep, W.P. Appl. Environ. Microbiol. (2005) [Pubmed]
  5. Characterization of bovine rumen liquor isoprenoid hydrocarbons with reference to dietary phytol. Body, D.R. Lipids (1977) [Pubmed]
  6. A case study on fuel oil contamination in a mangrove swamp in Hong Kong. Tam, N.F., Wong, T.W., Wong, Y.S. Mar. Pollut. Bull. (2005) [Pubmed]
  7. Burial, exportation and degradation of acyclic petroleum hydrocarbons following a simulated oil spill in bioturbated Mediterranean coastal sediments. Grossi, V., Massias, D., Stora, G., Bertrand, J.C. Chemosphere (2002) [Pubmed]
  8. Aliphatic hydrocarbons in wolf tissue samples from Galicia (N.W. Spain). Carril González-Barros, S.T., Alvarez Piñeiro, M.E., Simal Lozano, J., Lage Yusty, M.A. Chemosphere (1998) [Pubmed]
  9. Polycyclic aromatic hydrocarbons and other semivolatile organic compounds collected in New York City in response to the events of 9/11. Swartz, E., Stockburger, L., Vallero, D.A. Environ. Sci. Technol. (2003) [Pubmed]
  10. Characterization of aliphatic hydrocarbons in deep subsurface soils near the outskirts of Beijing, China. Zhu, Y.F., Liu, H., Xi, Z.Q., Cheng, H.X., Xu, X.B. Journal of environmental sciences (China). (2005) [Pubmed]
  11. Composition of the lipids of Nanoarchaeum equitans and their origin from its host Ignicoccus sp. strain KIN4/I. Jahn, U., Summons, R., Sturt, H., Grosjean, E., Huber, H. Arch. Microbiol. (2004) [Pubmed]
 
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