# Pristane

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Pristane
> Markdown URL: https://mediated.wiki/source/Pristane.md
> Source: https://en.wikipedia.org/wiki/Pristane
> Source revision: 1316880898
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{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](/source/Isocetane)|[Phytane](/source/Phytane)}}
}}
}}
'''Pristane''' is a natural [saturated](/source/Saturated_and_unsaturated_compounds) [terpenoid](/source/terpenoid) [alkane](/source/alkane) obtained primarily from [shark liver oil](/source/shark_liver_oil), from which its name is derived ([Latin](/source/Latin) ''pristis'', "shark"). It is also found in the [stomach oil](/source/stomach_oil) of birds in the order [Procellariiformes](/source/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](/source/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](/source/Miscibility) with water, but soluble in [diethyl ether](/source/diethyl_ether), [benzene](/source/benzene), [chloroform](/source/chloroform) and [carbon tetrachloride](/source/carbon_tetrachloride).

Pristane is known to induce autoimmune diseases in rodents. It is used in research to understand the [pathogenesis](/source/pathogenesis) of [rheumatoid arthritis](/source/rheumatoid_arthritis) and [lupus](/source/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](/source/immunologic_adjuvant), and an [anti-corrosion](/source/anti-corrosion) agent, biological marker, plasmocytomas inducer and in production of monoclonal antibodies.

Biosynthetically, pristane is derived from [phytol](/source/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](/source/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](/source/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

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Adapted from the Wikipedia article [Pristane](https://en.wikipedia.org/wiki/Pristane) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Pristane?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.