Pristane

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Pristane
Skeletal formula of pristane
Names
IUPAC name
2,6,10,14-Tetramethylpentadecane[1]
Identifiers
1720538
1921-70-6 YesY
ChEBI CHEBI:53181 YesY
ChemSpider 15182 YesY
24531975 6R,10R YesY
21428537 6R,10S YesY
24531981 6S,10S YesY
EC number 217-650-8
Jmol-3D images Image
MeSH pristane
PubChem 15979
RTECS number RZ1880000
Properties
C19H40
Molar mass 268.52 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
EU classification Irritant Xi
R-phrases R36/38
S-phrases S26, S36
Flash point >110 °C
Related compounds
Related alkanes
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY verify (what isYesY/N?)
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]

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., L. R. Garrett, P. E. Byers, and M. A. Cuchens (1989). "A survey of the amount of pristane in common fruits and vegetables". J. Food Comp. Anal. 2 (22): 22. doi:10.1016/0889-1575(89)90058-6. 
  3. ^ Anderson, P. N., and M. Potter (1969). "Induction of plasma cell tumours in BALB-c mice with 2,6,10,14-tetramethylpentadecane (pristane)". Nature 222 (5197): 994–5. doi:10.1038/222994a0. PMID 5789334. 
  4. ^ Hazani R, Engineer N. (Nov 2008). "Surreptitious injection of mineral oil: a case report of sclerosing lipogranulomatosis". Ann Plast Surg 61 (5): 555–8. doi:10.1097/SAP.0b013e31816d8316. PMID 18948786. 
  5. ^ Hahn, Bevra; Kono, Dwight (2013), "Animal Models of SLE", in Wallace, DJ, Dubois' Systemic Lupus Erythematosus and Related Diseases, Philadelphia: Saunders, pp. 190–236, doi:10.1016/B978-1-4377-1893-5.00017-0 
  6. ^ Hunt, J. (2002). "Early developments in petroleum geochemistry". Organic Geochemistry 33: 1025–1052. doi:10.1016/S0146-6380(02)00056-6.  edit
  7. ^ Goossens H., J.W. de Leeuw, P.A. Schenck, and S.C. Brassell (1984). "Tocopherols as likely precursors of pristane in ancient sediments and crude oils". Nature 312 (5993): 440–442. doi:10.1038/312440a0.