Rotundone

Rotundone
Names
IUPAC name
Guaia-1(5),11-dien-2-one
Systematic IUPAC name
(3S,5R,8S)-3,8-Dimethyl-5-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydroazulen-1(2H)-one
Identifiers
CAS Number
  • 18374-76-0 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 4478902
PubChem CID
  • 5321003
UNII
  • U33H52BQ0P checkY
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
  • 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
Chemical compound

Rotundone is a sesquiterpene originally discovered in the tubers of Java grass (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 wines.[1][2] It imparts a peppery aroma.[3]

References

  1. ^ 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.
  2. ^ "Overlooked pepper compound spices up red wine". Royal Society of Chemistry.
  3. ^ "Rotundone Imparts Peppery Aroma". Chemical & Engineering News.