Phenylisohexanol

Phenylisohexanol
Names
IUPAC name
3-methyl-5-phenylpentan-1-ol
Other names
  • Phenoxanol
  • Mefrosol
  • Phenoxanol
  • Phenylhexanol
Identifiers
3D model (JSmol)
ChEMBL
ECHA InfoCard 100.054.038 Edit this at Wikidata
EC Number
  • 259-461-3
UNII
  • InChI=1S/C12H18O/c1-11(9-10-13)7-8-12-5-3-2-4-6-12/h2-6,11,13H,7-10H2,1H3
    Key: OXYRENDGHPGWKV-UHFFFAOYSA-N
  • CC(CCC1=CC=CC=C1)CCO
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)
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H318
P264, P264+P265, P270, P280, P301+P317, P305+P354+P338, P317, P330, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

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.

Synthesis

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.

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.

Usage

Phenylisohexanol is used in cosmetics, perfumes, and deodorants, among other applications.

References

  1. ↑ "Phenylisohexanol". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-10-17.
  2. ↑ 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.
  3. ↑ CH655932A5, Tarchini, Claudio, "Pyran derivatives, process for their preparation and their use for the preparation of aliphatic alcohols", issued 1986-05-30
  4. ↑ 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.