1-(3-(methyl thio)-butyryl)-2,6,6-trimethyl cyclohexene

1-(3-(methylthio)-butyryl)-2,6,6-trimethylcyclohexene is an organic flavoring agent notable for its distinctive sweet fruity tobacco odor profile. This compound, with molecular formula C14H24OS, belongs to a class of sulfur-containing cyclohexene derivatives employed in flavor chemistry. It is also recognized under various synonymous names, including 3-(methylthio)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1-butanone. The chemistry reflects a ketone functional group attached to a substituted cyclohexene ring and a methylthio substituent. Information about this compound is cataloged in resources such as PubChem. Sourced mainly through synthetic chemical processes, this compound is utilized in flavor formulations to impart fruity and tobacco-like notes.

While 1-(3-(methylthio)-butyryl)-2,6,6-trimethylcyclohexene is not naturally abundant, it is synthetically produced for flavor applications. Its characteristic fruity tobacco aroma makes it valuable as a flavoring agent in food products. According to FEMA (US), identified by FEMA number 4569, it is approved for use strictly as a flavoring substance. Common application areas include confectionery frostings and fruit ices, where it is used in trace amounts to enhance sensory profiles. Use levels and acceptance fall under governance of flavoring safety standards including FEMA GRAS guidelines.

This compound exhibits physical properties consistent with a moderately nonpolar sulfur-containing ketone. It has a molecular weight of approximately 240.41 and a formula of C14H24O_S. Its boiling point ranges between 332°C and 334°C at atmospheric pressure, indicating low volatility at room temperature. The flash point measures approximately 156°C (311°F), conferring stability under normal handling conditions. The refractive index at 20°C varies from 1.505 to 1.511 reflecting its optical activity. Specific gravity is near 0.994 at 20°C, which is close to that of water but slightly less dense. The compound’s log P value is about 4.52 (estimated), indicating significant lipophilicity, consistent with limited aqueous solubility yet good solubility in alcohols. Vapor pressure is very low at 0.000137 mmHg at 25°C, suggesting limited evaporation at ambient temperatures. These properties influence its formulation in flavor matrices, favoring incorporation in lipid-rich or alcoholic settings rather than aqueous systems.

(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
FDA Substances Added to Food (formerly EAFUS):	View
HMDB (The Human Metabolome Database):	Search
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
FAO:	1-(3-(Methylthio)-butyryl)-2,6,6-trimethylcyclohexene

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:
flavoring agents
Recommendation for 1-(3-(methyl thio)-butyryl)-2,6,6-trimethyl cyclohexene usage levels up to:
	not for fragrance use.
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: 24
Click here to view publication 24
		average usual ppm	average maximum ppm
baked goods:		-	-
beverages(nonalcoholic):		-	-
beverages(alcoholic):		-	-
breakfast cereal:		-	-
cheese:		-	-
chewing gum:		-	-
condiments / relishes:		-	-
confectionery froastings:		0.00100	0.01000
egg products:		-	-
fats / oils:		-	-
fish products:		-	-
frozen dairy:		-	-
fruit ices:		0.00500	0.01000
gelatins / puddings:		0.00100	0.00500
granulated sugar:		-	-
gravies:		-	-
hard candy:		-	-
imitation dairy:		-	-
instant coffee / tea:		-	-
jams / jellies:		-	-
meat products:		-	-
milk products:		-	-
nut products:		-	-
other grains:		-	-
poultry:		-	-
processed fruits:		-	-
processed vegetables:		-	-
reconstituted vegetables:		-	-
seasonings / flavors:		-	-
snack foods:		-	-
soft candy:		-	-
soups:		-	-
sugar substitutes:		-	-
sweet sauces:		-	-

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 :20332432

National Institute of Allergy and Infectious Diseases:Data

3-(methylsulfanyl)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1-butanone

Chemidplus:0068697676