# Retene
> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Retene
> Markdown URL: https://mediated.wiki/source/Retene.md
> Source: https://en.wikipedia.org/wiki/Retene
> Source revision: 1146500769
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 434992161
| ImageFile = Retene.svg
| ImageSize =
| ImageName = Skeletal formula
| ImageFile1 = Retene-3D-balls.png
| ImageSize1 = 210px
| ImageName1 = Ball-and-stick model
| PIN = 1-Methyl-7-(propan-2-yl)phenanthrene
| OtherNames = Retene
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo =483-65-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0W2D2E1P9Q
| PubChem =10222
| EINECS = 207-597-9
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 9805
| InChI = 1/C18H18/c1-12(2)14-7-10-17-15(11-14)8-9-16-13(3)5-4-6-18(16)17/h4-12H,1-3H3
| InChIKey = NXLOLUFNDSBYTP-UHFFFAOYAL
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C18H18/c1-12(2)14-7-10-17-15(11-14)8-9-16-13(3)5-4-6-18(16)17/h4-12H,1-3H3
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = NXLOLUFNDSBYTP-UHFFFAOYSA-N
| SMILES =Cc1cccc3c1ccc2cc(C(C)C)ccc23
}}
|Section2={{Chembox Properties
| Formula =C18H18
| MolarMass =234.33552
| Appearance =
| Density =
| MeltingPtC = 98.5
| BoilingPtC = 390
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
'''Retene''', methyl isopropyl phenanthrene or 1-methyl-7-isopropyl phenanthrene, C18H18, is a [polycyclic aromatic hydrocarbon](/source/polycyclic_aromatic_hydrocarbon) present in the [coal tar](/source/coal_tar) fraction, [boiling](/source/boiling) above 360 °C. It occurs naturally in the [tar](/source/tar)s obtained by the [distillation](/source/distillation) of [resin](/source/resin)ous [wood](/source/wood)s. It crystallizes in large plates, which melt at 98.5 °C and boil at 390 °C. It is readily soluble in warm [ether](/source/diethyl_ether) and in hot [glacial acetic acid](/source/glacial_acetic_acid). [Sodium](/source/Sodium) and boiling [amyl alcohol](/source/amyl_alcohol) reduce it to a tetrahydroretene, but if it heated with [phosphorus](/source/phosphorus) and [hydriodic acid](/source/hydriodic_acid) to 260 °C, a dodecahydride is formed. [Chromic acid](/source/Chromic_acid) oxidizes it to retene quinone, [phthalic acid](/source/phthalic_acid) and [acetic acid](/source/acetic_acid). It forms a [picrate](/source/picrate) that melts at 123-124 °C.
Retene is derived by degradation of specific [diterpenoid](/source/diterpenoid)s biologically produced by [conifer](/source/conifer) trees. The presence of traces of retene in the air is an indicator of [forest fire](/source/forest_fire)s; it is a major product of [pyrolysis](/source/pyrolysis) of [conifer](/source/conifer) trees.[{{cite web|last1=Simonich|first1=Staci|title=Community Outreach and Education Program Presents Unsolved Mysteries of Human Health: How Scientists Study Toxic Chemicals|url=http://www.unsolvedmysteries.oregonstate.edu/GCMS_04.shtml|publisher=Oregon State University|archive-url=https://web.archive.org/web/20080316183140/http://www.unsolvedmysteries.oregonstate.edu/GCMS_04.shtml|archive-date=16 March 2008|url-status=dead|language=en|quote=The presence of the chemical retene (REE-teen) in the air is a good indication of burning vegetation.}}]{{Failed verification|date=September 2016|talk=Unsupported that a major part of conifer pyrolysis}} It is also present in [effluent](/source/effluent)s from [wood pulp](/source/wood_pulp) and [paper mill](/source/paper_mill)s.[{{cite journal|journal=Chemosphere|volume=37|pages=219–235|year=1998|author=J. Koistinen, M. Lehtonena, K. Tukia, M. Soimasuo, M. Lahtiperab and A. Oikari|title=Identification of lipophilic pollutants discharged from a finnish pulp and paper mill |pmid=9650265 | doi=10.1016/S0045-6535(98)00041-1|issue=2|bibcode=1998Chmsp..37..219K }}]
Retene, together with [cadalene](/source/cadalene), [simonellite](/source/simonellite) and ip-iHMN, is a [biomarker](/source/biomarker) of [vascular plant](/source/vascular_plant)s, which makes it useful for [paleobotanic](/source/paleobotanic) analysis of rock [sediment](/source/sediment)s. The ratio of retene/cadalene in sediments can reveal the ratio of the genus ''[Pinaceae](/source/Pinaceae)'' in the biosphere.[{{cite journal|journal=Geophysical Research Abstracts|volume=7|pages=10201|year=2005|title=Vascular plant biomarkers as ancient vegetation proxies and their stratigraphic use for tracing paleoclimatic changes during Jurassic in Western Europe|author=Y. Hautevelle, R. Michels, F. Malartre and A. Trouiller|url=http://www.cosis.net/abstracts/EGU05/10201/EGU05-J-10201.pdf|format=abstract}}]
==Health effects==
A recent study has shown retene, which is a component of the Amazonian organic [PM10](/source/PM10), is cytotoxic to human lung cells.[{{Cite journal|last=Nilmara de Oliveira Alves, Alexandre Teixeira Vessoni, Annabel Quinet, Rodrigo Soares Fortunato, Gustavo Satoru Kajitani, Milena Simões Peixoto, Sandra de Souza Hacon, Paulo Artaxo, Paulo Saldiva, Carlos Frederico Martins Menck, Silvia Regina Batistuzzo de Medeiros|date=September 7, 2017|title=Biomass burning in the Amazon region causes DNA damage and cell death in human lung cells.|journal=Scientific Reports|volume=7|issue=1 |page=10937 |doi=10.1038/s41598-017-11024-3|pmid=28883446 |pmc=5589902|bibcode=2017NatSR...710937D }}]
==References==
{{1911|wstitle=Retene|volume=23|page=202}}
Category:Petroleum products
Category:Phenanthrenes
Category:Biomarkers
Category:Isopropyl compounds
Category:Polycyclic aromatic hydrocarbons
---
Adapted from the Wikipedia article [Retene](https://en.wikipedia.org/wiki/Retene) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Retene?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.