Pristane

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Pristane
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
EC Number 217-650-8
MeSH pristane
RTECS number RZ1880000
Properties
C19H40
Molar mass 268.53 g·mol−1
Appearance Colorless 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 pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word 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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Infobox references

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]

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.[3][4][5]

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.[6] Tocopherols represent an alternate sedimentary source of pristane in sediments and petroleum.[7]

Toxicity of pristane alleviated by aconitine.[8]

References[edit]

  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. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.