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). verify (what is ?) Infobox references

Rose oxide^[1] 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[edit]

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.^[2]

Production[edit]

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[edit]

^ Ghodsi, Mohammadi Ziarani; Fatemeh, Mohajer; Seyedh, Mahboobeh Jamali; Nader, Ale Ebrahim (2020-11-30). "Quantitative and Qualitative Bibliometric Scope Toward the Synthesis of Rose Oxide as a Natural Product in Perfumery". Current Organic Synthesis. 17 (8): 610–624. doi:10.2174/1872208314666200722161044. PMID 32703138. S2CID 220731373.
^ 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.; 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] Ghodsi, Mohammadi Ziarani; Fatemeh, Mohajer; Seyedh, Mahboobeh Jamali; Nader, Ale Ebrahim (2020-11-30). "Quantitative and Qualitative Bibliometric Scope Toward the Synthesis of Rose Oxide as a Natural Product in Perfumery". Current Organic Synthesis. 17 (8): 610–624. doi:10.2174/1872208314666200722161044. PMID 32703138. S2CID 220731373.

[2] Dieter Martinetz und Roland Hartwig: Taschenlehrbuch der Riechstoffe: ein Lexikon von A–Z. Verlag Harri Deutsch 1998; ISBN 3-8171-1539-3; S. 330ff.

[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.

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