Retene
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| Names | |
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| Preferred IUPAC name
1-Methyl-7-(propan-2-yl)phenanthrene | |
| Other names
Retene
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| Identifiers | |
3D model (JSmol)
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| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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).
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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, but if it 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 that 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][failed verification – see discussion] 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 vascular plants, which makes it useful for paleobotanic analysis of rock sediments. The ratio of retene/cadalene in sediments can reveal the ratio of the genus Pinaceae in the biosphere.[3]
Health effects
[edit | edit source]A recent study has shown retene, which is a component of the Amazonian organic PM10, is cytotoxic to human lung cells.[4]
References
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This article incorporates text from a publication now in the public domain: Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
