Rose oxide

Rose oxide

Names
IUPAC name Tetrahydro-4-methyl-2-(2-methylpropenyl)-2H-pyran
Identifiers
CAS Number	16409-43-1 876-17-5 (−)-cis 876-18-6 (−)-trans 4610-11-1 (+)-cis 5258-10-6 (+)-trans
ChEBI	CHEBI:90075 CHEBI:90098 (−)-cis CHEBI:90100 (−)-trans CHEBI:90102 (+)-cis CHEBI:90103 (+)-trans
ChemSpider	25927 1361574 (−)-cis 5442476 (−)-trans 4937413 (+)-cis 1361573 (+)-trans
EC Number	240-457-5
Jmol interactive 3D	Image (−)-cis: Image (−)-trans: Image (+)-cis: Image (+)-trans: Image
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).
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Infobox references

Rose oxide is an organic compound of the pyran class and the monoterpene class and a fragrance found in roses and rose oil. 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] Rose oxide also contributes to the flavor of some fruits such as lychee and Gewürztraminer.

Rose oxide is 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. �R.; 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. replacement character in |first3= at position 4 (help)