EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

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

Supplier Sponsors

CAS Number: 18374-76-0Picture of molecule3D/inchi
Nikkaji Web:J13.921A
XlogP3-AA:3.70 (est)
Molecular Weight:218.33954000
Formula:C15 H22 O
NMR Predictor:Predict (works with chrome or firefox)
Category:flavor and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
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 Type: woody
Odor Strength:high ,
recommend smelling in a 1.00 % solution or less
woody peppery agarwood
Odor Description:at 1.00 % in dipropylene glycol. woody peppery agarwood
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the Chemical Sources Association
 
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
 
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
 average usual ppmaverage maximum ppm
baked goods: 0.001000.02000
beverages(nonalcoholic): 0.000100.00500
beverages(alcoholic): 0.000100.00500
breakfast cereal: --
cheese: --
chewing gum: 0.001000.02000
condiments / relishes: --
confectionery froastings: 0.000300.00500
egg products: 0.000300.00500
fats / oils: 0.020000.20000
fish products: 0.000300.00500
frozen dairy: 0.000200.00300
fruit ices: 0.000200.00300
gelatins / puddings: 0.000300.00200
granulated sugar: --
gravies: 0.001000.01000
hard candy: 0.001000.01000
imitation dairy: 0.001000.01000
instant coffee / tea: 0.000100.00100
jams / jellies: --
meat products: --
milk products: 0.001000.01000
nut products: 0.001000.01000
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: 0.100001.00000
snack foods: 0.001000.01000
soft candy: 0.001000.01000
soups: 0.000100.00200
sugar substitutes: --
sweet sauces: 0.001000.01000
 
Safety References:
EPI System: View
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
 
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
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (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
RSC Learn Chemistry:View
 
Potential Blenders and core components note
For Odor
amber
sarcocaulon mossamedense wood resinoid
FR
green
2,5-
dimethyl bicyclo(3.2.1)oct-2-ene
FR
spicy
agarospirol
FR
atractylis root oil
FR
4-
carvomenthenol
FL/FR
cascarilla oil replacer
FL/FR
mace absolute
FL/FR
mace fragrance
FR
mace oil
FL/FR
myrcene
FR
black
pepper oil
FL/FR
black
pepper oil replacer
FR
For Flavor
cooling
4-
carvomenthenol
FL/FR
spicy
cascarilla oil replacer
FL/FR
mace absolute
FL/FR
mace oil
FL/FR
black
pepper oil
FL/FR
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 agarwood
Search PMC Picture
 cypriol oil
Search Trop Picture
 patchouli oil
Search Trop Picture
 pepper black pepper
Search Trop Picture
 pepper white pepper
Search Trop Picture
 wines
Search Picture
 
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
 

Articles:

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.
 
Notes:
None found
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