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Rotundone

3,8-Dimethyl-5-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydroazulen-1(2H)-one

Rotundone

Sesquiterpene ketone (guaiane) · C₁₅H₂₂O

Chemical structure of Rotundone
2D structure PubChem / NCI CIR

Chemical info

CAS number CAS
18374-76-0
Molecular formula
C₁₅H₂₂O
Molecular weight
218.34 g/mol
Introduced
2008 (identified as pepper odorant) · Wood et al. (Australian Wine Research Institute)
Origin
Natural
Odor family
Cay Spicy
Note
Heart
Aroma
Peppery, woody, very potent; a notable share of people cannot smell it.

History

Rotundone had long been known from nut grass (Cyperus rotundus), which gave it its name. In 2008 Wood and colleagues showed that rotundone is the peppery odorant of Shiraz wine and also occurs in black and white pepper, marjoram and rosemary. The study noted that some participants could not perceive rotundone.

In perfumery

Rotundone occurs in some peppery woody materials made by oxidising patchouli oil. Pure, it has an extremely low odor threshold and is used only in traces.

Connections

Evokesblack pepper
Found in natureBlack pepper (Piper nigrum), Cypriol (Cyperus rotundus)

Regulatory status

Natural constituent · No IFRA standard
IFRA 51
No dedicated IFRA Standard in the 51st Amendment index.
EU allergen 2023/1545
Not named individually in the expanded allergen list of Regulation 2023/1545.

Sources

  1. Wikidata Q15424773 (CAS 18374-76-0, formula; data mirrored from PubChem)
  2. Wood C. et al. From wine to pepper: rotundone, an obscure sesquiterpene, is a potent spicy aroma compound. J. Agric. Food Chem. 56 (2008) 3738–3744
  3. The Good Scents Company Information System, material entries
  4. IFRA Standards, 51st Amendment: Index of IFRA Standards (notified 30 June 2023)