{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477172090| ImageFile = Pristane1.svg| ImageFile_Ref = {{chemboximage|correct|??}}| ImageName = Skeletal formula of pristane| IUPACName = 2,6,10,14-Tetramethylpentadecane<ref>{{Cite web|title=pristane - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/compound/15979|work=PubChem Compound|publisher=National Center for Biotechnology Information|location=USA|date=26 March 2005|at=Identification and Related Records}}</ref> |Section1={{Chembox Identifiers | CASNo = 1921-70-6 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 26HZV48DT1 | PubChem = 15979 | ChemSpiderID = 15182 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID1 = 24531975 | ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID1_Comment = <small>6''R'',10''R''</small> | ChemSpiderID2 = 21428537 | ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID2_Comment = <small>6''R'',10''S''</small> | ChemSpiderID3 = 24531981 | ChemSpiderID3_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID3_Comment = <small>6''S'',10''S''</small> | EINECS = 217-650-8 | MeSHName = pristane | ChEBI = 53181 | ChEBI_Ref = {{ebicite|correct|EBI}} | RTECS = RZ1880000 | Beilstein = 1720538 | SMILES = CC(C)CCCC(C)CCCC(C)CCCC(C)C | StdInChI = 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 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = XOJVVFBFDXDTEG-UHFFFAOYSA-N | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} }} |Section2={{Chembox Properties | C=19 | H=40 | Appearance = Colorless liquid | Odor = Odorless | Density = 783 mg mL<sup>−1</sup> | MeltingPtK = 173.2 | BoilingPtC = 296 | RefractIndex = 1.438 }} |Section3={{Chembox Thermochemistry | HeatCapacity = 569.76 J K<sup>−1</sup> mol<sup>−1</sup> }} |Section4={{Chembox Hazards | GHSPictograms = {{GHS exclamation mark}} | GHSSignalWord = '''WARNING''' | HPhrases = {{H-phrases|315}} | FlashPt = >110&nbsp;°C }} |Section5={{Chembox Related | OtherFunction_label = alkanes | OtherFunction = {{Unbulleted list|Isocetane|Phytane}} }} }} '''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.<ref>{{cite journal |doi=10.1016/0889-1575(89)90058-6 |title=A survey of the amount of pristane in common fruits and vegetables |journal=Journal of Food Composition and Analysis |volume=2 |issue=1 |pages=22–7 |year=1989 |last1=Chung |first1=J.-G |last2=Garrett |first2=L.R |last3=Byers |first3=P.E |last4=Cuchens |first4=M.A }}</ref> 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.<ref>{{cite journal |last1=Brooks |first1=J. D. |last2=Gould |first2=K. |last3=Smith |first3=J. W. |title=Isoprenoid Hydrocarbons in Coal and Petroleum |journal=Nature |date=April 1969 |volume=222 |issue=5190 |pages=257–259 |doi=10.1038/222257a0 |bibcode=1969Natur.222..257B |s2cid=4151186 }}</ref>

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.<ref name=pmid5789334>{{cite journal |doi=10.1038/222994a0 |pmid=5789334 |title=Induction of Plasma Cell Tumours in BALB/c Mice with 2,6,10,14-Tetramethylpentadecane (Pristane) |journal=Nature |volume=222 |issue=5197 |pages=994–5 |year=1969 |last1=Anderson |first1=Paul N |last2=Potter |first2=Michael |bibcode=1969Natur.222..994A |s2cid=4201897 }}</ref><ref name=pmid18948786>{{cite journal |doi=10.1097/SAP.0b013e31816d8316 |pmid=18948786 |title=Surreptitious Injection of Mineral Oil |journal=Annals of Plastic Surgery |volume=61 |issue=5 |pages=555–8 |year=2008 |last1=Hazani |first1=Ron |last2=Engineer |first2=Nitin |s2cid=875951 }}</ref><ref>{{cite book |doi=10.1016/B978-1-4377-1893-5.00017-0 |chapter=Animal Models of SLE |title=Dubois' Lupus Erythematosus and Related Syndromes |pages=190–236 |year=2013 |last1=Hahn |first1=Bevra Hannahs |last2=Kono |first2=Dwight |isbn=978-1-4377-1893-5 }}</ref>

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.<ref>{{cite journal |doi=10.1016/S0146-6380(02)00056-6 |title=Early developments in petroleum geochemistry |journal=Organic Geochemistry |volume=33 |issue=9 |pages=1025–52 |year=2002 |last1=Hunt |first1=John M |last2=Philp |first2=R.Paul |last3=Kvenvolden |first3=Keith A |bibcode=2002OrGeo..33.1025H }}</ref> Tocopherols represent an alternate sedimentary source of pristane in sediments and petroleum.<ref>{{cite journal |doi=10.1038/312440a0 |title=Tocopherols as likely precursors of pristane in ancient sediments and crude oils |journal=Nature |volume=312 |issue=5993 |pages=440–2 |year=1984 |last1=Goossens |first1=H |last2=De Leeuw |first2=J. W |last3=Schenck |first3=P. A |last4=Brassell |first4=S. C |bibcode=1984Natur.312..440G |s2cid=4329068 }}</ref>

Toxicity of pristane is alleviated by aconitine.<ref name=pmid28302448>{{cite journal |doi=10.1016/j.jphs.2017.01.007 |pmid=28302448 |title=Aconitine: A potential novel treatment for systemic lupus erythematosus |journal=Journal of Pharmacological Sciences |volume=133 |issue=3 |pages=115–121 |year=2017 |last1=Li |first1=Xiaodong |last2=Gu |first2=Liwei |last3=Yang |first3=Lan |last4=Zhang |first4=Dong |last5=Shen |first5=Jianying |doi-access=free }}</ref>

== References == {{Reflist}}

Category:Alkanes Category:Diterpenes