Pristane

Pristane
Names
	IUPAC name 2,6,10,14-Tetramethylpentadecane
	Other names Norphytane
Identifiers
CAS Number	1921-70-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	15182;
ECHA InfoCard	100.016.047
PubChem CID	15979;
CompTox Dashboard (EPA)	DTXSID70870919 ;
	InChI InChI=1/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 Key: XOJVVFBFDXDTEG-UHFFFAOYAG;
	SMILES C(CCCC(CCCC(C)CCCC(C)C)C)(C)C;
Properties
Chemical formula	C19H40
Molar mass	268.51 g/mol
Density	0.783 g/cm3
Melting point	−100 °C (−148 °F; 173 K)
Boiling point	296 °C (565 °F; 569 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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 mineral oil and some foods.^[1] 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.^[2]^[3] The fact that it is used in many products, raises the possibility that it may be a possible environmental exposure that may trigger diseases such as lupus and rheumatoid arthritis.^[4]

It is used as a lubricant, a transformer oil, an immunologic adjuvant, and an anti-corrosion agent.

Biosynthetically, pristane is derived from phytol.

References

^ 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. {{cite journal}}: Unknown parameter |voume= ignored (help)CS1 maint: multiple names: authors list (link)
^ Anderson, P. N., and M. Potter (1969). "Induction of plasma cell tunours in BALBfc mice with 2,6,10,14-tetramethylpentadecane (pristane)". Nature. 222 (5197): 994. doi:10.1038/222994a0. PMID 5789334.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Hazani R, Engineer N. (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. {{cite journal}}: Unknown parameter |month= ignored (help)
^ Frederick W Miller (2006). "Is occupational exposure to mineral oil a risk factor for rheumatoid arthritis?". Nature Clinical Practice Rheumatology. 2 (3): 130–131. doi:10.1038/ncprheum0137. PMID 16932671.

[1] 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. {{cite journal}}: Unknown parameter |voume= ignored (help)CS1 maint: multiple names: authors list (link)

[2] Anderson, P. N., and M. Potter (1969). "Induction of plasma cell tunours in BALBfc mice with 2,6,10,14-tetramethylpentadecane (pristane)". Nature. 222 (5197): 994. doi:10.1038/222994a0. PMID 5789334.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[3] Hazani R, Engineer N. (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. {{cite journal}}: Unknown parameter |month= ignored (help)

[4] Frederick W Miller (2006). "Is occupational exposure to mineral oil a risk factor for rheumatoid arthritis?". Nature Clinical Practice Rheumatology. 2 (3): 130–131. doi:10.1038/ncprheum0137. PMID 16932671.

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