Pristane

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Pristane
Skeletal formula of pristane Pristane.png
Skeletal formula of pristane
Names
IUPAC name
2,6,10,14-Tetramethylpentadecane [1]
Identifiers
3D model (JSmol)
1720538
ChEBI
ChemSpider
ECHA InfoCard 100.016.047 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 217-650-8
MeSH pristane
PubChem CID
RTECS number
  • RZ1880000
UNII
  • InChI=1S/C19H40/c1-16(2)10-7-12-18(5)14-9-15-19(6)13-8-11-17(3)4/h16-19H,7-15H2,1-6H3 Yes check.svgY
    Key: XOJVVFBFDXDTEG-UHFFFAOYSA-N Yes check.svgY
  • CC(C)CCCC(C)CCCC(C)CCCC(C)C
Properties
C19H40
Molar mass 268.529 g·mol−1
AppearanceColorless liquid
Odor Odorless
Density 783 mg mL−1
Melting point −100.0 °C; −147.9 °F; 173.2 K
Boiling point 296 °C (565 °F; 569 K)
1.438
Thermochemistry
569.76 J K−1 mol−1
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315
Flash point >110 °C
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pristane is a natural saturated terpenoid alkane obtained primarily from shark liver oil, from which its name is derived (Latin pristis, "shark"). It is also found in the stomach oil of birds in the order Procellariiformes and in mineral oil and some foods. [2] Pristane and phytane are used in the fields of geology and environmental science as biomarkers to characterize origins and evolution of petroleum hydrocarbons and coal. [3]

It is a transparent oily liquid that is immiscible with water, but soluble in diethyl ether, benzene, chloroform and carbon tetrachloride.

Pristane is known to induce autoimmune diseases in rodents. It is used in research to understand the pathogenesis of rheumatoid arthritis and lupus. [4] [5] [6]

It is used as a lubricant, a transformer oil, an immunologic adjuvant, and an anti-corrosion agent, biological marker, plasmocytomas inducer and in production of monoclonal antibodies.

Biosynthetically, pristane is derived from phytol and is used as a biomarker in petroleum studies. [7] Tocopherols represent an alternate sedimentary source of pristane in sediments and petroleum. [8]

Toxicity of pristane is alleviated by aconitine. [9]

References

  1. ↑ "pristane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records.
  2. ↑ Chung, J.-G; Garrett, L.R; Byers, P.E; Cuchens, M.A (1989). "A survey of the amount of pristane in common fruits and vegetables". Journal of Food Composition and Analysis. 2 (1): 22–7. doi:10.1016/0889-1575(89)90058-6.
  3. ↑ Brooks, J. D.; Gould, K.; Smith, J. W. (April 1969). "Isoprenoid Hydrocarbons in Coal and Petroleum". Nature. 222 (5190): 257–259. doi:10.1038/222257a0. S2CID   4151186.
  4. ↑ Anderson, Paul N; Potter, Michael (1969). "Induction of Plasma Cell Tumours in BALB/c Mice with 2,6,10,14-Tetramethylpentadecane (Pristane)". Nature. 222 (5197): 994–5. Bibcode:1969Natur.222..994A. doi:10.1038/222994a0. PMID   5789334. S2CID   4201897.
  5. ↑ Hazani, Ron; Engineer, Nitin (2008). "Surreptitious Injection of Mineral Oil". Annals of Plastic Surgery. 61 (5): 555–8. doi:10.1097/SAP.0b013e31816d8316. PMID   18948786. S2CID   875951.
  6. ↑ Hahn, Bevra Hannahs; Kono, Dwight (2013). "Animal Models of SLE". Dubois' Lupus Erythematosus and Related Syndromes. pp. 190–236. doi:10.1016/B978-1-4377-1893-5.00017-0. ISBN   978-1-4377-1893-5.
  7. ↑ Hunt, John M; Philp, R.Paul; Kvenvolden, Keith A (2002). "Early developments in petroleum geochemistry". Organic Geochemistry. 33 (9): 1025–52. doi:10.1016/S0146-6380(02)00056-6.
  8. ↑ Goossens, H; De Leeuw, J. W; Schenck, P. A; Brassell, S. C (1984). "Tocopherols as likely precursors of pristane in ancient sediments and crude oils". Nature. 312 (5993): 440–2. Bibcode:1984Natur.312..440G. doi:10.1038/312440a0. S2CID   4329068.
  9. ↑ Li, Xiaodong; Gu, Liwei; Yang, Lan; Zhang, Dong; Shen, Jianying (2017). "Aconitine: A potential novel treatment for systemic lupus erythematosus". Journal of Pharmacological Sciences. 133 (3): 115–121. doi: 10.1016/j.jphs.2017.01.007 . PMID   28302448.
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