Rotundone

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Rotundone
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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
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3D model (JSmol)
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  • 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
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).

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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

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  1. ^ Page Module:Citation/CS1/styles.css has no content.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. ^ Page Module:Citation/CS1/styles.css has no content."Overlooked pepper compound spices up red wine". Royal Society of Chemistry.
  3. ^ Page Module:Citation/CS1/styles.css has no content."Rotundone Imparts Peppery Aroma". Chemical & Engineering News.
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