Rose oxide

Rose oxide
Names

IUPAC name Tetrahydro-4-methyl-2-(2-methylpropenyl)-2H-pyran
Identifiers
CAS Number	16409-43-1^Y 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
InChI InChI=1S/C10H18O/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3 Key: CZCBTSFUTPZVKJ-UHFFFAOYSA-N (−)-cis: InChI=1S/C10H18O/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3/t9-,10-/m1/s1 Key: CZCBTSFUTPZVKJ-NXEZZACHSA-N (−)-trans: InChI=1S/C10H18O/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3/t9-,10+/m1/s1 Key: CZCBTSFUTPZVKJ-ZJUUUORDSA-N (+)-cis: InChI=1S/C10H18O/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3/t9-,10-/m0/s1 Key: CZCBTSFUTPZVKJ-UWVGGRQHSA-N (+)-trans: InChI=1S/C10H18O/c1-8(2)6-10-7-9(3)4-5-11-10/h6,9-10H,4-5,7H2,1-3H3/t9-,10+/m0/s1 Key: CZCBTSFUTPZVKJ-VHSXEESVSA-N
SMILES CC1CCOC(C1)C=C(C)C (−)-cis: C[C@@H]1CCO[C@@H](C1)C=C(C)C (−)-trans: C[C@@H]1CCO[C@H](C1)C=C(C)C (+)-cis: C[C@H]1CCO[C@H](C1)C=C(C)C (+)-trans: C[C@H]1CCO[C@@H](C1)C=C(C)C
Properties
Chemical formula	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 ^YN ?)
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

↑ Dieter Martinetz und Roland Hartwig: Taschenlehrbuch der Riechstoffe: ein Lexikon von A–Z. Verlag Harri Deutsch 1998; ISBN 3-8171-1539-3; S. 330ff.
↑ 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.