(3S,5R,8S)-3,8-dimethyl-5-prop-1-en-2-yl-3,4,5,6,7,8-hexahydro-2H-azulen-1-one
(-)-rotundone
Identification
| Name | (3S,5R,8S)-3,8-dimethyl-5-prop-1-en-2-yl-3,4,5,6,7,8-hexahydro-2H-azulen-1-one |
| CAS Number | 18374-76-0 |
| FDA UNII | U33H52BQ0P |
| Molecular Formula | C15 H22 O |
| Molecular Weight | 218.33954000 |
| Nikkaji Number | J13.921A |
Regulatory
| FEMA Number | 4867 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 1.975 mg/L @ 25 °C (est) |
Organoleptic Properties
| Odor Description | at 1.00 % in dipropylene glycol. |
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| baked goods | 0.00100 |
| beverages(nonalcoholic) | 0.00010 |
| beverages(alcoholic) | 0.00010 |
| breakfast cereal | - |
| cheese | - |
| chewing gum | 0.00100 |
| condiments / relishes | - |
| confectionery froastings | 0.00030 |
| egg products | 0.00030 |
| fats / oils | 0.02000 |
| fish products | 0.00030 |
| frozen dairy | 0.00020 |
| fruit ices | 0.00020 |
| gelatins / puddings | 0.00030 |
| granulated sugar | - |
| gravies | 0.00100 |
| hard candy | 0.00100 |
| imitation dairy | 0.00100 |
| instant coffee / tea | 0.00010 |
| jams / jellies | - |
| meat products | - |
| milk products | 0.00100 |
| nut products | 0.00100 |
| other grains | - |
| poultry | - |
| processed fruits | - |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | 0.10000 |
| snack foods | 0.00100 |
| soft candy | 0.00100 |
| soups | 0.00010 |
| sugar substitutes | - |
| sweet sauces | 0.00100 |
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Exchange of knowledge
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Potential Uses
Natural Occurrence
Synonyms
1(2H)-
azulenone, 3,4,5,6,7,8-hexahydro-3,8-dimethyl-5-(1-methylethenyl)-, (3S,5R,8S)-
(-)-
guaia-1(5),11-dien-2-one
(-)-
rotundone
PubMed:
Identification and Characterization of 3-epi-Rotundone, a Novel Stereoisomer of Rotundone, in Several Kinds of Fruits.
PubMed:
Quantitation of Rotundone in Grapefruit (Citrus paradisi) Peel and Juice by Stable Isotope Dilution Assay.
PubMed:
Identification of Rotundone as a Potent Odor-Active Compound of Several Kinds of Fruits.
PubMed:
Characterisation of aroma-active and off-odour compounds in German rainbow trout (Oncorhynchus mykiss). Part II: Case of fish meat and skin from earthen-ponds farming.
PubMed:
Comparison data of common and abundant terpenes at different grape development stages in Shiraz wine grapes.
PubMed:
Distribution of Rotundone and Possible Translocation of Related Compounds Amongst Grapevine Tissues in Vitis vinifera L. cv. Shiraz.
PubMed:
Constituents of Cypriol Oil (Cyperus scariosus R.Br.): N-Containing Molecules and Key Aroma Components.
PubMed:
Straightforward strategy for quantifying rotundone in wine at ngL(-1) level using solid-phase extraction and gas chromatography-quadrupole mass spectrometry. Occurrence in different varieties of spicy wines.
PubMed:
Fragrant Sesquiterpene Ketones as Trace Constituents in Frankincense Volatile Oil of Boswellia sacra.
PubMed:
Terpene evolution during the development of Vitis vinifera L. cv. Shiraz grapes.
PubMed:
Key enzymes behind black pepper aroma in wines.
PubMed:
Cytochrome P450 CYP71BE5 in grapevine (Vitis vinifera) catalyzes the formation of the spicy aroma compound (-)-rotundone.
PubMed:
Two key polymorphisms in a newly discovered allele of the Vitis vinifera TPS24 gene are responsible for the production of the rotundone precursor α-guaiene.
PubMed:
Environmental Factors and Seasonality Affect the Concentration of Rotundone in Vitis vinifera L. cv. Shiraz Wine.
PubMed:
Carbocations and the Complex Flavor and Bouquet of Wine: Mechanistic Aspects of Terpene Biosynthesis in Wine Grapes.
PubMed:
Within-Vineyard, Within-Vine, and Within-Bunch Variability of the Rotundone Concentration in Berries of Vitis vinifera L. cv. Shiraz.
PubMed:
Shiraz wines made from grape berries (Vitis vinifera) delayed in ripening by plant growth regulator treatment have elevated rotundone concentrations and "pepper" flavor and aroma.
PubMed:
Comparison of the formation of peppery and woody sesquiterpenes derived from α-guaiene and α-bulnesene under aerial oxidative conditions.
PubMed:
Mechanistic studies on the autoxidation of α-guaiene: structural diversity of the sesquiterpenoid downstream products.
PubMed:
Production of the pepper aroma compound, (-)-rotundone, by aerial oxidation of α-guaiene.
PubMed:
Characterization of the key aroma compounds in Shiraz wine by quantitation, aroma reconstitution, and omission studies.
PubMed:
Biosynthesis of sesquiterpenes in grape berry exocarp of Vitis vinifera L.: evidence for a transport of farnesyl diphosphate precursors from plastids to the cytosol.
PubMed:
Vineyard and fermentation studies to elucidate the origin of 1,8-cineole in Australian red wine.
PubMed:
Relationship of changes in rotundone content during grape ripening and winemaking to manipulation of the 'peppery' character of wine.
PubMed:
Effective analysis of rotundone at below-threshold levels in red and white wines using solid-phase microextraction gas chromatography/tandem mass spectrometry.
PubMed:
Determination of rotundone, the pepper aroma impact compound, in grapes and wine.
PubMed:
From wine to pepper: rotundone, an obscure sesquiterpene, is a potent spicy aroma compound.