Ionone
From Wikipedia, the free encyclopedia
| Ionone | |
|---|---|
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| IUPAC name | α: (3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one β: (3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one |
| Other names | cyclocitrylideneacetone, irisone, jonon |
| Properties | |
| Molecular formula | C13H20O |
| Molar mass | 192.3004 g/mol |
| Density | 0.933 g/cm3 (alpha) 0.945 g/cm3 (beta) |
| Melting point |
-49 °C (beta) |
| Boiling point |
126°C - 128°C at 12 mmHg |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Ionone or 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one or cyclocitrylideneacetone or irisone C13H20O is a chemical substance and part of the terpene family. Ionone is an aroma compound. It is a pale yellow liquid with a woody, dry, fruity, raspberry and violet smell. It is a raw material for the production of retinol.
Beta ionone (right) has a less pronounced odor than alpha ionone (left).
[edit] Organic synthesis
Ionone can be synthesised from citral and acetone with Calcium oxide as a basic heterogeneous catalysis[1] and serves as an example of an Aldol condensation followed by a rearrangement reaction.
The nucleophilic addition of the carbanion 3 of acetone 1 to the carbonylgroup on citral 4 is base catalysed. The aldol condensation product 5 eliminates water through the enolate ion 6 to the pseudoionone 7.
The reaction proceeds by acid catalysis where the double bond in 7 opens to form the carbocation 8. A rearrangement reaction of the carbocation follows with ring closure to 9. Finally a hydrogen atom can be abstracted from 9 by an acceptor molecule (Y) to form either 10 (extended conjugated system) or 11.
[edit] References
- [1] NODA, C., ALT, G. P., WERNECK, R. M. et al. Aldol Condensation of Citral with Acetone on Basic Solid Catalysts. Braz. J. Chem. Eng., June 1998, vol.15, no.2. ISSN 0104-6632. [1] open access publication
- Pseudoionone Alfred Russell and R. L. Kenyon Organic Syntheses, Coll. Vol. 3, p.747; Vol. 23, p.78 Article
