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

General Material Information

Preferred name	(3S,5R,8S)-3,8-dimethyl-5-prop-1-en-2-yl-3,4,5,6,7,8-hexahydro-2H-azulen-1-one
Trivial Name	(-)-Rotundone
Short Description	(-)-rotundone
Formula	C15 H22 O
CAS Number	18374-76-0
FEMA Number	4867
FDA UNII	U33H52BQ0P
Nikkaji Number	J13.921A
xLogP3-AA	3.70 (est)
NMR Predictor	External link
FDA Patent	No longer provide for the use of these seven synthetic flavoring substances
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 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, (-)- 1(2H)-Azulenone, 3,4,5,6,7,8-hexahydro-3,8-dimethyl-5-(1-methylethenyl)-, [3S-(3α,5α,8α)]- (3S,5R,8S)-3,4,5,6,7,8-Hexahydro-3,8-dimethyl-5-(1-methylethenyl)-1(2H)-azulenone (-)-Rotundone Rotundone

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Literature & References

	(3S,5R,8S)-3,8-dimethyl-5-prop-1-en-2-yl-3,4,5,6,7,8-hexahydro-2H-azulen-1-one
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	5321003
Pubchem (cas):	18374-76-0

Publications by PubMed
Identification and Characterization of 3-epi-Rotundone, a Novel Stereoisomer of Rotundone, in Several Kinds of Fruits.
Quantitation of Rotundone in Grapefruit (Citrus paradisi) Peel and Juice by Stable Isotope Dilution Assay.
Identification of Rotundone as a Potent Odor-Active Compound of Several Kinds of Fruits.
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.
Comparison data of common and abundant terpenes at different grape development stages in Shiraz wine grapes.
Distribution of Rotundone and Possible Translocation of Related Compounds Amongst Grapevine Tissues in Vitis vinifera L. cv. Shiraz.
Constituents of Cypriol Oil (Cyperus scariosus R.Br.): N-Containing Molecules and Key Aroma Components.
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.
Fragrant Sesquiterpene Ketones as Trace Constituents in Frankincense Volatile Oil of Boswellia sacra.
Terpene evolution during the development of Vitis vinifera L. cv. Shiraz grapes.
Key enzymes behind black pepper aroma in wines.
Cytochrome P450 CYP71BE5 in grapevine (Vitis vinifera) catalyzes the formation of the spicy aroma compound (-)-rotundone.
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.
Environmental Factors and Seasonality Affect the Concentration of Rotundone in Vitis vinifera L. cv. Shiraz Wine.
Carbocations and the Complex Flavor and Bouquet of Wine: Mechanistic Aspects of Terpene Biosynthesis in Wine Grapes.
Within-Vineyard, Within-Vine, and Within-Bunch Variability of the Rotundone Concentration in Berries of Vitis vinifera L. cv. Shiraz.
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.
Comparison of the formation of peppery and woody sesquiterpenes derived from α-guaiene and α-bulnesene under aerial oxidative conditions.
Mechanistic studies on the autoxidation of α-guaiene: structural diversity of the sesquiterpenoid downstream products.
Production of the pepper aroma compound, (-)-rotundone, by aerial oxidation of α-guaiene.
Characterization of the key aroma compounds in Shiraz wine by quantitation, aroma reconstitution, and omission studies.
Biosynthesis of sesquiterpenes in grape berry exocarp of Vitis vinifera L.: evidence for a transport of farnesyl diphosphate precursors from plastids to the cytosol.
Vineyard and fermentation studies to elucidate the origin of 1,8-cineole in Australian red wine.
Relationship of changes in rotundone content during grape ripening and winemaking to manipulation of the 'peppery' character of wine.
Effective analysis of rotundone at below-threshold levels in red and white wines using solid-phase microextraction gas chromatography/tandem mass spectrometry.
Determination of rotundone, the pepper aroma impact compound, in grapes and wine.
From wine to pepper: rotundone, an obscure sesquiterpene, is a potent spicy aroma compound.

Other Information

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
tgsc:	Atomic Weights use for this web site
(IUPAC):	Periodic Table of the Elements
KEGG (GenomeNet):	C17501
HMDB (The Human Metabolome Database):	HMDB36443
FooDB:	FDB015330
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View

Suppliers

Carbosynth

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	218.33953857422
Solubility
water, 1.975 mg/L @ 25 °C (est)	Yes

Organoleptic Properties

Odor Type: Woody
woody, peppery, agarwood
General comment	At 1.00 % in dipropylene glycol. woody peppery agarwood

Occurrences

Safety Information

Safety information


Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice

Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 28
Click here to view publication 28
	average usual ppm	average maximum ppm
baked goods:	0.00100	0.02000
beverages(nonalcoholic):	0.00010	0.00500
beverages(alcoholic):	0.00010	0.00500
breakfast cereal:	-	-
cheese:	-	-
chewing gum:	0.00100	0.02000
condiments / relishes:	-	-
confectionery froastings:	0.00030	0.00500
egg products:	0.00030	0.00500
fats / oils:	0.02000	0.20000
fish products:	0.00030	0.00500
frozen dairy:	0.00020	0.00300
fruit ices:	0.00020	0.00300
gelatins / puddings:	0.00030	0.00200
granulated sugar:	-	-
gravies:	0.00100	0.01000
hard candy:	0.00100	0.01000
imitation dairy:	0.00100	0.01000
instant coffee / tea:	0.00010	0.00100
jams / jellies:	-	-
meat products:	-	-
milk products:	0.00100	0.01000
nut products:	0.00100	0.01000
other grains:	-	-
poultry:	-	-
processed fruits:	-	-
processed vegetables:	-	-
reconstituted vegetables:	-	-
seasonings / flavors:	0.10000	1.00000
snack foods:	0.00100	0.01000
soft candy:	0.00100	0.01000
soups:	0.00010	0.00200
sugar substitutes:	-	-
sweet sauces:	0.00100	0.01000

Safety references

EPI System: View

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :5321003

National Institute of Allergy and Infectious Diseases:Data

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

Chemidplus:0018374760