(3S,5R,8S)-3,8-dimethyl-5-prop-1-en-2-yl-3,4,5,6,7,8-hexahydro-2H-azulen-1-one

(-)-rotundone

CAS: 18374-76-0 C15 H22 O MW: 218.33954000 woody

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 Number18374-76-0
FDA UNIIU33H52BQ0P
Molecular FormulaC15 H22 O
Molecular Weight218.33954000
Nikkaji NumberJ13.921A

Regulatory

FEMA Number4867
FDANo 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 ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavor and fragrance agents
RIFM Fragrance Material Safety AssessmentSearch
baked goods0.00100
beverages(nonalcoholic)0.00010
beverages(alcoholic)0.00010
breakfast cereal-
cheese-
chewing gum0.00100
condiments / relishes-
confectionery froastings0.00030
egg products0.00030
fats / oils0.02000
fish products0.00030
frozen dairy0.00020
fruit ices0.00020
gelatins / puddings0.00030
granulated sugar-
gravies0.00100
hard candy0.00100
imitation dairy0.00100
instant coffee / tea0.00010
jams / jellies-
meat products-
milk products0.00100
nut products0.00100
other grains-
poultry-
processed fruits-
processed vegetables-
reconstituted vegetables-
seasonings / flavors0.10000
snack foods0.00100
soft candy0.00100
soups0.00010
sugar substitutes-
sweet sauces0.00100

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Exchange of knowledge

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Potential Uses

None Found

Natural Occurrence

agarwood PMC cypriol oil patchouli oil pepper black pepper pepper white pepper wines

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.