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
EC Number	240-457-5
E number
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)	{{#property:P3117}}
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 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.

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.

Rose oxide synthesis