Rotundone

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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
3D model (JSmol)
ChemSpider
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UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • 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).

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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