Pristane

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]

Pristane

Names
IUPAC name 2,6,10,14-Tetramethylpentadecane[1]
Identifiers
CAS Number	1921-70-6 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1720538
ChEBI	CHEBI:53181 Y
ChemSpider	15182 Y 24531975 6R,10R N 21428537 6R,10S N 24531981 6S,10S N
ECHA InfoCard	100.016.047
EC Number	217-650-8
MeSH	pristane
PubChem CID	15979
RTECS number	RZ1880000
UNII	26HZV48DT1 Y
CompTox Dashboard (EPA)	DTXSID70870919
InChI 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 Y Key: XOJVVFBFDXDTEG-UHFFFAOYSA-N Y
SMILES CC(C)CCCC(C)CCCC(C)CCCC(C)C
Properties
Chemical formula	C19H40
Molar mass	268.529 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)
Refractive index (nD)	1.438
Thermochemistry
Heat capacity (C)	569.76 J K−1 mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315
Flash point	>110 °C
Related compounds
Related alkanes	Isocetane Phytane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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.