Phenylisohexanol
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| Names | |
|---|---|
| IUPAC name
3-methyl-5-phenylpentan-1-ol | |
| Other names
phenoxanol, mefrosol, phenylhexanol | |
| Identifiers | |
3D model (JSmol) |
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| ECHA InfoCard | 100.054.038 |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C12H18O | |
| Molar mass | 178.275 g·mol−1 |
| Density | 0,955-0,963 g/cm3 |
| Boiling point | 260–261 °C (500–502 °F; 533–534 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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Phenylisohexanol is a synthetically made organic compound, used as a rose smell fragrance at industrial scale. The substance is also known under the brand names: phenoxanol (International Flavors & Fragrances), mefrosol (Givaudan, formerly Quest International), and phenylhexanol (Firmenich).
Properties
[edit]Phenylisohexanol occurs as a clear, colorless to light yellow liquid and has a fresh rose oil scent that lingers long after use. Phenylisohexanol is a primary alkyl aryl alcohol and is chemically related to citronellol. However, the isobutenyl group from citronellol is replaced by a phenyl group. The odor detection threshold of phenylisohexanol is approximately 0.8 µg /m³, ten times lower than that of citronellol.[1]
Synthesis
[edit]The starting materials for the synthesis of phenylisohexanol are isoprene and benzaldehyde. The oxo-Diels–Alder reaction between the two components forms 2-phenyl-4-methyl-3,6-dihydropyrane (CAS number 60335-71-9), also known as rosyran. Ring opening by hydrogenolysis in acidic center of the dihydropyrane ring yields racemic phenylisohexanol.[2]
The commercial product is a racemic mixture of the two stereoisomers, (R)-(+)- and (S)-(-)-phenylisohexanol. With asymmetric synthesis, it is possible to produce the R- or S- isomer separately.[3]
Usage
[edit]Phenylisohexanol is used in cosmetics, perfumes, and deodorants, among other applications.
References
[edit]- ↑ Kraft, Philip; Bajgrowicz, Jerzy A.; Denis, Caroline; Fráter, Georg (September 2000). "Odds and Trends: Recent Developments in the Chemistry of Odorants". Angewandte Chemie International Edition. 39 (17): 2980–3010. Bibcode:2000AngCh..39.2980K. doi:10.1002/1521-3773(20000901)39:17<2980::AID-ANIE2980>3.0.CO;2-#. ISSN 1433-7851. PMID 11028024.
- ↑ CH655932A, "CH655932A"
- ↑ Matteoli, Ugo; Ciappa, Alessandra; Bovo, Sara; Bertoldini, Matheo; Scrivanti, Alberto (2007-04-16). "Asymmetric catalysis in fragrance chemistry: a new synthetic approach to enantiopure Phenoxanol®, Citralis® and Citralis Nitrile®". Tetrahedron: Asymmetry. 18 (6): 797–802. doi:10.1016/j.tetasy.2007.03.014. ISSN 0957-4166.