Rotundone

• CAT Number: M086527
• CAS Number: 18374-76-0
• Molecular Formula: C15H22O
• Molecular Weight: 218.34
• Purity: ≥95%
• Synonyms: (-)-Rotundone; (3S,5R,8S)-3,4,5,6,7,8-Hexahydro-3,8-dimethyl-5-(1-methylethenyl)-1(2H)-azulenone
• Storage: Store at -20°C
• IUPAC Name: (3S,5R,8S)-3,8-dimethyl-5-prop-1-en-2-yl-3,4,5,6,7,8-hexahydro-2H-azulen-1-one
• 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
• InChIKey: NUWMTBMCSQWPDG-SDDRHHMPSA-N
• SMILES: CC1CCC(CC2=C1C(=O)CC2C)C(=C)C

Rotundone (CAS 18374-76-0) 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 wines. It imparts a peppery aroma.The proposed biosynthetic scheme for rotundone involves both the methylerythritol phosphate (MEP) and the mevalonate (MVA) pathways. 

Reference

1.Geffroy, Olivier, Didier Kleiber, and Alban Jacques. "May peppery wines be the spice of life? A review of research on the ‘pepper’aroma and the sesquiterpenoid rotundone." OENO One 54.2 (2020): 245-262.
2.Wood, Claudia, et al. "From wine to pepper: rotundone, an obscure sesquiterpene, is a potent spicy aroma compound." Journal of Agricultural and Food Chemistry 56.10 (2008): 3738-3744.