Rose oxide

Rose oxide
Names
IUPAC name
Tetrahydro-4-methyl-2-(2-methylpropenyl)-2H-pyran
Identifiers
16409-43-1 YesY
876-17-5 ()-cis N
876-18-6 ()-trans N
4610-11-1 (+)-cis N
5258-10-6 (+)-trans N
3D model (Jmol) Interactive image
()-cis: Interactive image
()-trans: Interactive image
(+)-cis: Interactive image
(+)-trans: Interactive image
ChEBI CHEBI:90075 N
CHEBI:90098 ()-cis N
CHEBI:90100 ()-trans N
CHEBI:90102 (+)-cis N
CHEBI:90103 (+)-trans N
ChemSpider 25927 N
1361574 ()-cis N
5442476 ()-trans N
4937413 (+)-cis N
1361573 (+)-trans N
ECHA InfoCard 100.036.763
EC Number 240-457-5
PubChem 27866
1712087 ()-cis
7093102 ()-trans
6432154 (+)-cis
1712086 (+)-trans
Properties
C10H18O
Molar mass 154.25 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Rose oxide is a fragrance chemical found in roses and rose oil. It also contributes to the flavor of some fruits, such as lychee, and wines, such as Gewürztraminer.

Chemistry

Rose oxide is an organic compound of the pyran class of monoterpenes. The compound has a cis- and a trans-isomer, each with a (+)- and ()-stereoisomer, but only the ()-cis isomer (odor threshold 0.5 ppb) is responsible for the typical rose (floral green) fragrance.[1]

Production

Rose oxide can be produced industrially beginning with photooxygenation of citronellol to give the allyl hydroperoxide which is then reduced with sodium sulfite to provide the diol. Ring-closure with sulfuric acid forms both the cis- and trans-isomers in equal amounts.[2]

References

  1. Dieter Martinetz und Roland Hartwig: Taschenlehrbuch der Riechstoffe: ein Lexikon von A–Z. Verlag Harri Deutsch 1998; ISBN 3-8171-1539-3; S. 330ff.
  2. Alsters, P. L.; Jary, W. .; Nardello-Rataj, V.; Aubry, J. M. (2010). ""Dark" Singlet Oxygenation of β-Citronellol: A Key Step in the Manufacture of Rose Oxide". Organic Process Research & Development. 14: 259. doi:10.1021/op900076g.
This article is issued from Wikipedia - version of the 5/22/2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.