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Retene

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Retene
Skeletal formula
Ball-and-stick model
Names
IUPAC name
7-Isopropyl-1-methylphenanthrene
Other names
Retene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.908 Edit this at Wikidata
EC Number
  • 207-597-9
  • InChI=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 ☒N
    Key: NXLOLUFNDSBYTP-UHFFFAOYSA-N ☒N
  • 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
    Key: NXLOLUFNDSBYTP-UHFFFAOYAL
  • Cc1cccc3c1ccc2cc(C(C)C)ccc23
Properties
C18H18
Molar mass 234.33552
Melting point 98.5 °C (209.3 °F; 371.6 K)
Boiling point 390 °C (734 °F; 663 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Retene, methyl isopropyl phenanthrene or 1-methyl-7-isopropyl phenanthrene, C18H18, is a polycyclic aromatic hydrocarbon present in the coal tar fraction, boiling above 360 °C. It occurs naturally in the tars obtained by the distillation of resinous woods. It crystallizes in large plates, which melt at 98.5 °C and boil at 390 °C. It is readily soluble in warm ether and in hot glacial acetic acid. Sodium and boiling amyl alcohol reduce it to a tetrahydroretene, whilst if it be heated with phosphorus and hydriodic acid to 260 °C, a dodecahydride is formed. Chromic acid oxidizes it to retene quinone, phthalic acid and acetic acid. It forms a picrate which melts at 123-124 °C.

Retene is derived by degradation of specific diterpenoids biologically produced by conifer trees.

The presence of traces of retene in the air is an indicator of forest fires; it is a major product of pyrolysis of conifer trees.[1] It is also present in effluents from wood pulp and paper mills.[2]

Retene, together with cadalene, simonellite and ip-iHMN, is a biomarker of higher plants, which makes it useful for paleobotanic analysis of rock sediments. Ratio of retene/cadalene in sediments can reveal the ratio of the genus Pinaceae in the biosphere.[3]

References

  1. ^ Unsolved Mysteries of Human Health, Community Outreach and Education Program, Oregon State University
  2. ^ J. Koistinen, M. Lehtonena, K. Tukia, M. Soimasuo, M. Lahtiperab and A. Oikari (1998). "IDENTIFICATION OF LIPOPHILIC POLLUTANTS DISCHARGED FROM A FINNISH PULP AND PAPER MILL". Chemosphere. 37 (2): 219–235. doi:10.1016/S0045-6535(98)00041-1. PMID 9650265.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ Y. Hautevelle, R. Michels, F. Malartre and A. Trouiller (2005). "Vascular plant biomarkers as ancient vegetation proxies and their stratigraphic use for tracing paleoclimatic changes during Jurassic in Western Europe" (abstract). Geophysical Research Abstracts. 7: 10201.{{cite journal}}: CS1 maint: multiple names: authors list (link)

Public Domain This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press. {{cite encyclopedia}}: Missing or empty |title= (help)

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