Thujene
As thujene a group of terpenes called. These are the isomers of α-thuya, β-thuya and sabinene . Thujenes are bicyclic , unsaturated compounds that differ in the position of their double bond and the spatial arrangement of their substituents .
Representative
| Thujene | |||||||
| Surname | (-) - α-thuja | (+) - α-thuja | (+) - Sabinen | (-) - Sabinen | |||
| other names | (-) - 3-thuja | (+) - 3-thuja | (+) - 4 (10) -Thujen | (-) - 4 (10) -Thujen | |||
| (1 R * , 5 R * ) - (±) -2-methyl-5- (1-methylethyl) bicyclo [3.1.0] hex-2-ene | (1 R * , 5 R * ) - (±) -4-methylene-1- (1-methylethyl) bicyclo [3.1.0] hexane | ||||||
| Structural formula |
-(%E2%80%93)-3-Thujen_Formula_V.1.svg)
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-(%2B)-3-Thujen_Formula_V.1.svg)
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-(%2B)-Sabinen_Formula_V.1.svg)
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-(%E2%80%93)-Sabinen_Formula_V.1.svg)
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| CAS number | 3917-48-4 | 2009-00-9 546-79-2 (hydrate) |
10408-16-9 | ||||
| 2867-05-2 ( racemate ) | 3387-41-5 (racemate) | ||||||
| Molecular formula | C 10 H 16 | ||||||
| Molar mass | 136.24 g mol −1 | ||||||
| Physical state | liquid | ||||||
| Brief description | oil | colorless oil (racemate) | |||||
| boiling point | 152 ° C (699 hPa) | 163-165 ° C (racemate) | |||||
| density | 0.84 g cm −3 (racemate) | ||||||
| solubility | insoluble in water (racemate) | ||||||
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GHS labeling |
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| H and P phrases | see above | see above | 226 | ||||
| see above | see above | no EUH phrases | |||||
| see above | see above | 210-280-303 + 361 + 353 | |||||
Occurrence
Thujene are natural substances which are found in the Semen tree oil [(+) - Sabinen, 30%], in the medicinal plant Zanthoxylum rhetsa [(-) - Sabinen], in the resin of Boswellia serrata [(+) - α-Thujen], in the mango leaf oil ( Mangifera indica ) and in the oil of the occidental tree of life [(-) - α-Thujen].
2-thuja (β-thuja) has not yet been detected in nature.
biosynthesis
The biosynthesis of α-thuja and sabinene takes place from α-terpinene . The required terpine cation is obtained from geranyl pyrophosphate .
Individual evidence
- ↑ a b c Entry on Thujene. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.
- ↑ a b c d e Sabinen data sheet (PDF) from Carl Roth , accessed on April 13, 2010.
- ^ R. Croteau, EM Davis, T. Hartmann, T. Hemscheidt, B. Shen, EM Stocking, RM Williams, JF Sanz-Cervera, JC Vederas (eds.), FJ Leeper (eds.): Biosynthesis: Aromatic Polyketides, Isoprenoids, Alkaloids , Springer Verlag, Berlin, 1st edition, 2000 , pp. 61-63. ISBN 3-540-66573-0 .