Retene

Retene

Names
IUPAC name 7-Isopropyl-1-methylphenanthrene
Other names Retene
Identifiers
CAS Number	483-65-8
ChemSpider	9805
EC Number	207-597-9
Jmol interactive 3D	Image
PubChem	10222
InChI 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 Key: NXLOLUFNDSBYTP-UHFFFAOYSA-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
SMILES Cc1cccc3c1ccc2cc(C(C)C)ccc23
Properties
Chemical formula	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).
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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.^[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.
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.

 This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press.