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;
UNII	4O51437J50 ; 08FS7459GK (−)-cis ; XF860DJU9P (−)-trans ; 7G7H98N31J (+)-cis ; 0338MA4H3Y (+)-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).
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	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] The first time, in 2020, biblometric scope toward the synthesis of Rose Oxide was published.[2]

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.[3]

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.
Ziarani, Ghodsi Mohammadi; Mohajer, Fatemeh; Jamali, Seyedh Mahboobeh; Ebrahim, Nader Ale (2020-07-22). "Quantitative and Qualitative bibliometric scope toward the Synthesis of Rose Oxide as a Natural Product in perfumery". Current Organic Synthesis. 17. doi:10.2174/1872208314666200722161044. PMID 32703138.
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: 259–262. doi:10.1021/op900076g.

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[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] Ziarani, Ghodsi Mohammadi; Mohajer, Fatemeh; Jamali, Seyedh Mahboobeh; Ebrahim, Nader Ale (2020-07-22). "Quantitative and Qualitative bibliometric scope toward the Synthesis of Rose Oxide as a Natural Product in perfumery". Current Organic Synthesis. 17. doi:10.2174/1872208314666200722161044. PMID 32703138.

[3] 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: 259–262. doi:10.1021/op900076g.