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 Y 876-18-6 (−)-trans Y 4610-11-1 (+)-cis Y 5258-10-6 (+)-trans Y
3D model (JSmol)	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 CID	27866 1712087 (−)-cis 7093102 (−)-trans 6432154 (+)-cis 1712086 (+)-trans
UNII	4O51437J50 Y 08FS7459GK (−)-cis Y XF860DJU9P (−)-trans Y 7G7H98N31J (+)-cis Y 0338MA4H3Y (+)-trans Y
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
Density	0.875 g/cm3
Boiling point	230 °C (446 °F; 503 K)
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 oxide¹ is a fragrance chemical found in roses and rose oil.²³ It also contributes to the flavor of some fruits, such as lychee,⁴ and wines, such as Gewürztraminer.

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.⁵⁶

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.⁷