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Retene
Retene.png
IUPAC name
Other names Retene
Identifiers
CAS number 483-65-8
PubChem 10222
SMILES
Properties
Molecular formula C18H18
Molar mass 234.33552
Melting point

98.5 °C

Boiling point

390 °C

Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.

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.[2]

References

  1. ^ Unsolved Mysteries of Human Health, Community Outreach and Education Program, Oregon State University
  2. ^ 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. http://www.cosis.net/abstracts/EGU05/10201/EGU05-J-10201.pdf.  

This article incorporates text from the Encyclopædia Britannica, Eleventh Edition, a publication now in the public domain.

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1911 encyclopedia

Up to date as of January 14, 2010

From LoveToKnow 1911

RETENE (methyl isopropyl phenanthrene), CisHis, a hydrocarbon present in the coal-tar fraction, boiling above 360° C.; it also occurs 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, - t 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.


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