Rotundone

Rotundone
Names
	IUPAC name (3S,5R,8S)-5-Isopropenyl-3,8-dimethyl-3,4,5,6,7,8-hexahydro-1(2H)-azulenone
Identifiers
CAS Number	18374-76-0;
3D model (JSmol)	Interactive image;
ChemSpider	4478902;
PubChem CID	5321003;
	InChI InChI=1S/C15H22O/c1-9(2)12-6-5-10(3)15-13(8-12)11(4)7-14(15)16/h10-12H,1,5-8H2,2-4H3/t10-,11-,12+/m0/s1 Key: NUWMTBMCSQWPDG-SDDRHHMPSA-N; InChI=1/C15H22O/c1-9(2)12-6-5-10(3)15-13(8-12)11(4)7-14(15)16/h10-12H,1,5-8H2,2-4H3/t10-,11-,12+/m0/s1 Key: NUWMTBMCSQWPDG-SDDRHHMPBR;
	SMILES O=C1\C2=C(/[C@H](C1)C)C[C@H](\C(=C)C)CC[C@@H]2C;
Properties
Chemical formula	C15H22O
Molar mass	218.340 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Rotundone is a sesquiterpene originally discovered in the tubers of Cyperus rotundus. Rotundone is also present in the essential oils of black pepper, marjoram, oregano, rosemary, basil, thyme, and geranium, as well as in some Syrah (Shiraz) wines.[1][2] It imparts a peppery aroma.[3]

References

Siebert, Tracey E.; Wood, Claudia; Elsey, Gordon M.; Pollnitz, Alan P. (2008). "Determination of Rotundone, the Pepper Aroma Impact Compound, in Grapes and Wine". Journal of Agricultural and Food Chemistry. 56 (10): 3745–8. doi:10.1021/jf800184t. PMID 18461962.
"Overlooked pepper compound spices up red wine". Royal Society of Chemistry.
"Rotundone Imparts Peppery Aroma". Chemical & Engineering News.

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