Pristane
 | |
| Names | |
|---|---|
| IUPAC name
2,6,10,14-Tetramethylpentadecane[1] | |
| Identifiers | |
1921-70-6  | |
| 3D model (Jmol) | Interactive image |
| 1720538 | |
| ChEBI | CHEBI:53181 |
| ChemSpider | 15182 24531975 6R,10R  21428537 6R,10S 24531981 6S,10S |
| ECHA InfoCard | 100.016.047 |
| EC Number | 217-650-8 |
| MeSH | pristane |
| PubChem | 15979 |
| 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) |
| Refractive index (nD) |
1.438 |
| Thermochemistry | |
| 569.76 J K−1 mol−1 | |
| Hazards | |
| GHS pictograms |  |
| GHS signal word | WARNING |
| H315 | |
| EU classification (DSD) |
 Xi |
| R-phrases | R36/38 |
| S-phrases | S26, S36 |
| 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). | |
| 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 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
- ↑ "pristane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records.
- ↑ 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.
- ↑ Anderson, P. N. & 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.
- ↑ 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.
- ↑ 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
- ↑ Hunt, J. (2002). "Early developments in petroleum geochemistry". Organic Geochemistry. 33: 1025–1052. doi:10.1016/S0146-6380(02)00056-6.
- ↑ Goossens H.; J.W. de Leeuw; P.A. Schenck & 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.