Pinocamphone
The pinocamphones (also: pinocamphene ) are a group of chemical compounds that occur naturally in hyssop oil and belong to the bicyclic monoterpene ketones.
Representative
| Pinocamphone | |||||
| Surname | (+) - Pinocamphone | (-) - Pinocamphone | (+) - isopinocamphone | (-) - Isopinocamphone | |
| Structural formula |
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-Pinocamphon_Formula_V1.svg)
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| Structural formula |
-3-Pinanon_Formula_V1.svg)
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| other names | (1 R , 2 S , 5 S ) -pinocamphone | (1 S , 2 R , 5 R ) -pinocamphone | (1 R , 2 R , 5 S ) -pinocamphone | (1 S , 2 S , 5 R ) -pinocamphone | |
| 3-pinanone 2,6,6-trimethylbicyclo [3.1.1] heptan-3-one |
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| CAS number | 18492-59-6 | 22339-21-5 | 473-62-1 | 14575-93-0 | |
| 547-60-4 (racemate) 30517-87-4 (racemate) |
15358-88-0 (racemate) | ||||
| PubChem | 11038 | ||||
| Molecular formula | C 10 H 16 O | ||||
| Molar mass | 152.23 g mol −1 | ||||
| Physical state | liquid | ||||
| Brief description | |||||
| boiling point | 211-213 ° C | ||||
| density | 0.96 g cm −3 | ||||
| Refractive index | 1.472 (21 ° C) | ||||
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GHS labeling |
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| H and P phrases | see above | ||||
| see above | |||||
| see above | |||||
| Toxicological data | > 250 mg kg −1 ( LD 50 , mouse , oral ) | ||||
Occurrence
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The pinocamphone and structurally similar compounds account for up to 70 percent of hyssop oil (Hyssopi aetherolum). These include between 7 and 25% 1-pinocamphone, 16 to 22% isopinocamphone, 10 to 23% pinocarvone and 7 to 11% pinene . Pinocamphon and isopinocamphon are held responsible for the toxic effects of hyssop oil. They are also found in other natural substances such as labdanum . Since pinocamphone is carcinogenic, the use of hyssop oil as a fragrance is banned in the USA.
Extraction and presentation
Pinocamphon was first obtained in 1892 by Otto Wallach by reducing nitrosopins with zinc in an acetic acid solution. However, the natural occurrence was only discovered by Schimmel & Co. in 1908.
The compound can also be obtained by thermolysis of α-pinene epoxide in isopropyl alcohol in the absence of water.
Individual evidence
- ↑ a b c d The Terpenes Volume II The Dicyclic Terpenes, Sesquiterpenes and their Derivatives . 1932, p. 194 ( limited preview in Google Book search).
- ^ A b Robert Tisserand, Rodney Young: Essential Oil Safety A Guide for Health Care Professionals . Elsevier Health Sciences, 2013, ISBN 978-0-7020-5434-1 , pp. 621 ( limited preview in Google Book search).
- ↑ OHLOFF: Earthly Fragrances - Heavenly Lust A cultural history of fragrances . Springer-Verlag, 2013, ISBN 978-3-0348-6160-1 , p. 82 ( limited preview in Google Book search).
- ^ Franz von Bruchhausen: Hager's Handbook of Pharmaceutical Practice . Springer-Verlag, 1998, ISBN 3-540-52688-9 , pp. 870 ( limited preview in Google Book search).
- ^ H. Panda: Cultivation and Utilization of Aromatic Plants . ASIA PACIFIC BUSINESS PRESS Inc., 2005, ISBN 81-7833-027-X ( limited preview in Google Book Search).
- ↑ The Terpenes Volume II The dicyclic Terpenes, Sesquiterpenes and Their Derivatives . 1932, p. 192 ( limited preview in Google Book search).
- ↑ Vladimir Anikeev, Maohong Fan I: Supercritical Fluid Technology for Energy and Environmental Applications . Newnes, 2013, ISBN 978-0-444-62697-4 , pp. 72 ( limited preview in Google Book search).