caramel furanone

Caramel furanone, commonly known as sotolone, is a lactone-type organic compound with the molecular formula C₆H₈O₃. It presents as a yellowish to amber liquid or crystalline substance possessing a remarkably potent caramellic and maple-like aroma. This compound is recognized under multiple synonyms including caramel lactone, fenugreek lactone, and dimethyl oxyfurone. It is extensively utilized as a flavoring agent to impart sweet, burnt sugar, and cotton candy notes in various food and beverage products. Naturally, caramel furanone occurs in several foods such as maple syrup, fenugreek seed, coffee, and certain wines. The chemical is listed in the PubChem database for structural and chemical property referencing. Its sensory significance and flavor profile contribute to its valued role in flavor formulation contexts.

Caramel furanone occurs naturally in diverse plant and food sources including coffee, fenugreek seed, buckwheat honey, maple syrup, pineapple fruit, sake, sherry, rice wine, and Virginia tobacco. This presence underlines its biological and sensory relevance in food products and beverages. Its flavor profile, characterized by caramellic, maple, and brown sugar notes, makes it useful for flavoring applications in both food and drink industries. The compound is employed as a flavoring agent to evoke sweet, burnt sugar, and cotton candy sensations. According to FEMA (The Flavor and Extract Manufacturers Association, US), caramel furanone is identified with FEMA number 3634 and is classified for use as a flavoring substance. It contributes to aroma profiles in products such as baked goods, beverages, confectionery, and savory items, enhancing flavors like allspice, banana, butterscotch, cinnamon, coconut, coffee, maple, pineapple, and vanilla. Its inclusion in flavor formulations follows regulated standards for safety and efficacy.

Caramel furanone possesses physical and chemical properties that influence its application in flavor formulations. It has a molecular weight of approximately 128.13 g/mol and a molecular formula of C₆H₈O₃. The compound melts at temperatures ranging between 25 and 29°C at atmospheric pressure (760 mm Hg) and exhibits a boiling point from 93 to 95°C under reduced pressure (2 mm Hg). Its flash point is about 212°F (approximately 100°C), which informs on handling safety concerning flammability. Estimated partition coefficient (logP octanol-water) is −0.296, indicating moderate hydrophilicity. Caramel furanone is soluble in alcohol and estimated to be soluble in water at around 222,800 mg/L at 25°C, though the solubility classification sometimes varies between 'yes' and 'no'. Stability profiles reveal good endurance in alcoholic fine fragrances but reduced stability in hypochlorite bleach and certain detergent formulations. These properties affect its behavior in mixtures, volatility, and interaction with solvents and substrates in flavor creation.

Leffingwell:	Chirality or Article
	3-hydroxy-4,5-dimethyl-5H-furan-2-one
NIST Chemistry WebBook:	Search Inchi
Canada Domestic Sub. List:	28664-35-9
Pubchem (cid):	62835
Pubchem (sid):	135021025
Flavornet:	28664-35-9

(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
CHEBI:	View
CHEMBL:	View
HMDB (The Human Metabolome Database):	HMDB31306
FooDB:	FDB003360
YMDB (Yeast Metabolome Database):	YMDB01572
Export Tariff Code:	2905.32.0000
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View
EFSA Update of results on the monitoring of furan levels in food:	Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:	Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:	Read Report

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 20/22 - Harmful by inhalation and if swallowed. R 36/37 - Irritating to eyes and respiratory system. S 02 - Keep out of the reach of children. S 07 - Keep container tightly closed. S 09 - Keep container in a well-ventilated place. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 35 - This material and its container must be disposed of in a safe way. S 36 - Wear suitable protective clothing. S 36/37/39 - Wear suitable clothing, gloves and eye/face protection. S 46 - If swallowed, seek medical advice immediately and show this container or label.
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 caramel furanone usage levels up to:
	not for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU):		1.80 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA):		0.10 (μg/capita/day)
Structure Class:		III
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: 12. Update in publication number(s): 29
Click here to view publication 12
		average usual ppm	average maximum ppm
baked goods:		10.00000	20.00000
beverages(nonalcoholic):		-	-
beverages(alcoholic):		0.01000	5.00000
breakfast cereal:		-	-
cheese:		-	-
chewing gum:		1.00000	5.00000
condiments / relishes:		2.50000	10.00000
confectionery froastings:		-	-
egg products:		-	-
fats / oils:		0.10000	10.00000
fish products:		2.00000	10.00000
frozen dairy:		-	-
fruit ices:		-	-
gelatins / puddings:		-	-
granulated sugar:		-	-
gravies:		2.00000	10.00000
hard candy:		-	-
imitation dairy:		-	-
instant coffee / tea:		-	-
jams / jellies:		-	-
meat products:		2.00000	10.00000
milk products:		-	-
nut products:		-	-
other grains:		-	-
poultry:		2.00000	10.00000
processed fruits:		-	-
processed vegetables:		-	-
reconstituted vegetables:		-	-
seasonings / flavors:		0.10000	20.00000
snack foods:		-	-
soft candy:		-	-
soups:		2.00000	10.00000
sugar substitutes:		-	-
sweet sauces:		2.50000	10.00000

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission related to - Flavouring Group Evaluation 10: Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - (Commission Regulation (EC) No 1565/2000 of 18 July 2000) View page or View pdf

Flavouring Group Evaluation 64 (FGE.64): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (57th meeting) structurally related to aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 evaluated by EFSA in FGE.10Rev1 (EFSA, 2008ab) View page or View pdf

Flavouring Group Evaluation 217: alpha,beta-Unsaturated ketones and precursors from chemical subgroup 4.1 of FGE.19: Lactones[1] View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 92 (FGE.92): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (68th meeting) structurally related to aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones evaluated by EFSA in FGE.10Rev1 (2009) View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 217, Revision 1 (FGE.217Rev1). Consideration of genotoxic potential for a,ß-unsaturated ketones and precursors from chemical subgroup 4.1 of FGE.19: Lactones View page or View pdf

Scientific Opinion on the safety and efficacy of furanones and tetrahydrofurfuryl derivatives: 5-ethyl-3-hydroxy-4-methylfuran-2(5H)-one and 3-hydroxy-4,5-dimethylfuran-2(5H)-one (chemical group 13) when used as flavourings for all animal species View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 217 Revision 2 (FGE.217Rev2), consideration of genotoxic potential for a,ß-unsaturated ketones and precursors from chemical subgroup 4.1 of FGE.19: lactones View page or View pdf

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EPA Substance Registry Services (TSCA):28664-35-9

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Laboratory Chemical Safety Summary :62835

National Institute of Allergy and Infectious Diseases:Data

WGK Germany:3

3-hydroxy-4,5-dimethyl-5H-furan-2-one

Chemidplus:0028664359