caramel furanone
4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one

Sponsors

Name: 3-hydroxy-4,5-dimethyl-5H-furan-2-one
CAS Number: 28664-35-9Picture of molecule3D/inchi
Other: 87021-36-1
ECHA EINECS - REACH Pre-Reg: 249-136-4
Nikkaji Web: J68.557G
MDL: MFCD00059957
CoE Number: 11834
XlogP3-AA: 0.40 (est)
Molecular Weight: 128.12736000
Formula: C6 H8 O3
NMR Predictor: Predict (works with chrome or firefox)
Category: flavoring 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
Perfumer and Flavorist: Search
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
JECFA Food Flavoring: 243 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one
Flavis Number: 10.030 (Old)
DG SANTE Food Flavourings: 10.030 3-hydroxy-4,5-dimethylfuran-2(5H)-one
FEMA Number: 3634 4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one
 
Physical Properties:
Appearance: white to pale yellow liquid to solid (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 25.00 to 29.00 °C. @ 760.00 mm Hg
Boiling Point: 93.00 to 95.00 °C. @ 2.00 mm Hg
Boiling Point: 81.00 °C. @ 6.00 mm Hg
Flash Point: > 212.00 °F. TCC ( > 100.00 °C. )
logP (o/w): -0.296 (est)
Soluble in:
 alcohol
 water, 2.228e+005 mg/L @ 25 °C (est)
Insoluble in:
 water
Stability:
 alcoholic fine fragrance, good
 antiperspirant, fair
 fabric softener, fair
 hypochlorite bleach, poor
 liquid detergent, fair
 perborate powder detergent, poor
 soap, fair
 
Organoleptic Properties:
Odor Type: caramellic
Odor Strength: very high ,
recommend smelling in a 0.01 % solution or less
Substantivity: > 400 hour(s) at 3.00 % in propylene glycol
 sweet caramellic maple sugar burnt sugar coffee
Odor Description:
at 0.01 % in propylene glycol.
extremely sweet strong caramel maple burnt sugar coffee
Luebke, William tgsc, (1998)
 sweet caramellic maple sugar brown sugar cotton candy
Odor Description:
Sweet, caramellic, maple, brown sugar, cyclotene and cotton candy
Mosciano, Gerard P&F 22, No. 4, 75, (1997)
Flavor Type: caramellic
 sweet maple sugar brown sugar cotton candy sugar burnt sugar
Taste Description:
sweet maple brown sugar cotton candy burnt sugar
 sweet caramellic maple sugar brown sugar cotton candy
Taste Description:
at 50.00 ppm.
Sweet, caramellic, maple, brown sugary and cotton candy
Mosciano, Gerard P&F 22, No. 4, 75, (1997)
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Advanced Biotech
CARAMEL FURANONE SYNTHETIC
97% min.
Odor: Caramel, Sweet
Anhui Haibei
3-Hydroxy-4,5-dimethyl-2(5H)-furanone
Odor: Extremely sweet strong caramel maple burnt sugar coffee
Aromiens International
Caramel Furanone Natural
Aromiens International
Caramel Furanone
Artiste
Caramel Furanone Natural
Available as solutions (1%, 5%, 15%, etc.) in various solvents.
Aurochemicals
FENUGREEK LACTONE, Natural
Beijing Lys Chemicals
Caramel furanone
Berjé
Caramel Furanone 100%
Happening at Berje
BOC Sciences
For experimental / research use only.
CARAMEL FURANONE (3% IN TRIACETIN)
DeLong Chemicals America
4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-one
Excellentia International
Caramel Furanone (4,5-Dimethyl-3-Hydroxy-2(5H)-Furanone) Natural
H. Interdonati, Inc.
Caramel Furanone Kosher
Featured Products
Kun Shan P&A
Caramel Furanone
M&U International
FENUGREEK LACTONE, Kosher
M&U International
NAT.FENUGREEK LACTONE
M&U International
SOTOLONE, Kosher
Penta International
CARAMEL FURANONE, PURE, Kosher
Phoenix Aromas & Essential Oils
Caramel Furanone (all solutions)
Reincke & Fichtner
4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-one
Riverside Aromatics
FENUGREEK LACTONE [SOTOLONE]
Robertet
Sotolone
Sigma-Aldrich
4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-one, ≥97%, FG
Odor: caramel; celery; maple; tobacco; earthy; green; meaty; wine-like; nutty; seedy; smoky
Certified Food Grade Products
Soda Aromatic
Sugar Lactone
Odor: very powerful, roasted sugar-like
SRS Aromatics
SUGAR LACTONE PURE
Tengzhou Xiang Yuan Aroma Chemicals
4,5-Dimethyl-3-hydroxy-2,5H-furanone
Treatt
4-Methoxy-2,5-dimethyl-3(2H)furanone
Vigon International
Fenugreek Lactone (Sotolone)
Odor: Extremely Strong,Fenugreek,Lovage,Maple
Vigon International
Sotolone Natural (dimethyl Oxyfurone)
 
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
 average usual ppmaverage maximum ppm
baked goods: -10.00000
beverages(nonalcoholic): --
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: -10.00000
confectionery froastings: --
egg products: --
fats / oils: -10.00000
fish products: -10.00000
frozen dairy: --
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: -10.00000
hard candy: --
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: -10.00000
milk products: --
nut products: --
other grains: --
poultry: -10.00000
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: -10.00000
sugar substitutes: --
sweet sauces: -10.00000
 
Safety References:
Flavor & Extract Manufacturers Association (FEMA) reference(s):
The FEMA GRAS assessment of lactones used as flavor ingredients.View pdf
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,-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
EPI System: View
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
EPA Substance Registry Services (TSCA): 28664-35-9
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
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
 
References:
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
 
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
FDA Everything Added to Food in the United States (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
RSC Learn Chemistry: 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
 
Potential Blenders and core components note
For Odor
For Flavor
No flavor group found for these
2-
acetyl-3,4,5,6-tetrahydropyridine
FL
allyl 2-furoate
FL
benzyl disulfide
FL
2,5-
diethyl tetrahydrofuran
FL
furfuryl acetone
FL
mango furanone
FL
acidic
acidic
dextro,laevo-
tartaric acid
FL
burnt
furfuryl alcohol
FL
buttery
butter maple flavor
FL
diacetyl
FL
caramellic
5-
ethyl-3,4,5,6-tetramethyl cyclohexen-2-one
FL
honey maple flavor
FL
lucuma flavor
FL
3-
methyl butyl 2-furyl butyrate
FL
pyruvaldehyde
FL
coffee
2-
thiophene thiol
FL
corn chip
2-
acetyl-2-thiazoline
FL
fatty
2,4-
undecadienal
FL
(E,E)-2,4-
undecadienal
FL
fruity
furfuryl valerate
FL
2-
pentanoyl furan
FL
herbal
5-
hydroxymethyl furfural
FL
meaty
2-
mercaptomethyl pyrazine
FL
nutty
3,5(6)-
cocoa pyrazine
FL
peanut oxazole
FL
sweet
caramel dione
FL
molasses flavor
FL
dextro-
sorbitol
FL
waxy
furfuryl octanoate
FL
 
Potential Uses:
 allspiceFL
 bananaFL
 bay rum 
 blackberryFL
 butterscotchFL
 caramelFL
 cinnamonFL
 coconutFL
 coffeeFL
 cotton candyFL
 cranberryFL
 fenugreekFL/FR
 figFL
 fir 
 fir balsam 
 gingerbread 
 honeysuckle chevrefeuille 
 mangoFL
 mapleFL
 melonFL
 mulberryFL
 musk 
 nutFL
 papayaFL
 passion fruit 
 peachFL
 pina coladaFL
 pineappleFL
 pomegranateFL
 pumpkinFL
 sugar brownFL
 tobacco tabac tabaco 
 toffeeFL
 tonka 
 vanillaFL
 
Occurrence (nature, food, other): note
 coffee
Search PMC Picture
 fenugreek seed
Search Trop Picture
 honey buckwheat honey
PbMd Search PMC Picture
 maple
Search PMC Picture
 pineapple fruit
Search Trop Picture
 sake
Search PMC Picture
 sherry
Search PMC Picture
 tobacco virginia tobacco
Search Picture
 wine rice wine
Search Picture
 
Synonyms:
 caramel furanone 100%
 caramel furanone natural
 caramel furanone pure
 caramel furanone synthetic
 caramel furanone, neat
 caramel lactone
 dimethyl oxyfurone
4,5-dimethyl-3-hydroxy-2,5-dihydro-2-furanone
4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one
4,5-dimethyl-3-hydroxy-2(5H)-furanone
2,3-dimethyl-4-hydroxy-2,5-dihydrofuran-5-one
 fenugreek lactone
2-hydroxy-3-methyl-2-penten-4-olide
2-hydroxy-3,4-dimethyl-2-buten-1,4-olide
3-hydroxy-4,5-dimethyl furan-2(5H)-one
3-hydroxy-4,5-dimethyl-2(5H)-furanone
3-hydroxy-4,5-dimethyl-5-hydrofuran-2-one
3-hydroxy-4,5-dimethyl-5H-furan-2-one
3-hydroxy-4,5-dimethylfuran-2(5H)-one
 soloton
 sotolon (Givaudan)
 sotolone
 sugar lactone
 

Articles:

US Patents: 4,428,886 - Novel intermediates for the preparation of .alpha.-hydroxycarbonyl compounds
PubMed: UHPLC quantification of sotolon in white wine.
PubMed: Milk volatile organic compounds and fatty acid profile in cows fed timothy as hay, pasture, or silage.
PubMed: Protective effect of Trigonella foenum-graecum Linn. on monosodium glutamate-induced dyslipidemia and oxidative stress in rats.
PubMed: Effect of grain type and toasting conditions of barrels on the concentration of the volatile substances released by the wood and on the sensory characteristics of Montepulciano d'Abruzzo.
PubMed: Analytical characterization of the aroma of five premium red wines. Insights into the role of odor families and the concept of fruitiness of wines.
PubMed: Characterization of odor-active compounds in Californian chardonnay wines using GC-olfactometry and GC-mass spectrometry.
PubMed: 4-Hydroxyisoleucine: effects of synthetic and natural analogues on insulin secretion.
 
Notes:
Can get some extraordinary blends if you shade it well. Key flavour compd. found in raw cane sugar, aged sake, coffee, fenugreek, lovage and wines Sotolon (also known as sotolone) is a lactone and an extremely powerful aroma compound, with the typical smell of fenugreek or curry at high concentrations and maple syrup, caramel, or burnt sugar at lower concentrations. (Wikipedia)
 
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