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 ;
3D model (JSmol)	Interactive image; (−)-cis: Interactive image; (−)-trans: Interactive image; (+)-cis: Interactive image; (+)-trans: Interactive image;
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 ;
ECHA InfoCard	100.036.763
EC Number	240-457-5;
PubChem CID	27866; 1712087 (−)-cis; 7093102 (−)-trans; 6432154 (+)-cis; 1712086 (+)-trans;
CompTox Dashboard (EPA)	DTXSID1051771 ;
	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). verify (what is ?) 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

^ 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. �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. {{cite journal}}: replacement character in |first3= at position 4 (help)

[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. {{cite journal}}: replacement character in |first3= at position 4 (help)

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