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Furaneol

CAS No.3658-77-3
Chemical Name:Furaneol
CBNumber:CB1205015
Molecular Formula:C6H8O3
Formula Weight:128.13
MOL File:3658-77-3.mol

Furaneol Property

Melting point 73-77 °C(lit.)
Boiling point 188 °C
Density 1.049 g/mL at 25 °C
vapor pressure 0.81Pa at 25℃
refractive index n20/D 1.439
FEMA 3174 | 4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE
Flash point >230 °F
storage temp. 2-8°C
solubility Chloroform (Slightly), Methanol (Slightly)
pka 9.62±0.40(Predicted)
form Solid
color White
Odor at 1.00 % in propylene glycol. sweet cotton candy caramel strawberry sugar
Odor Type caramellic
biological source synthetic
Water Solubility 176g/L at 20℃
JECFA Number 1446
BRN 1281357
Stability Light Sensitive, Temperature Sensitive
InChIKey INAXVXBDKKUCGI-UHFFFAOYSA-N
LogP 0.95 at 20℃
CAS DataBase Reference 3658-77-3(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS) 4-HYDROXY-2,5-DIMETHYL-3(2H)-FURANONE
FDA UNII 20PI8YZP7A
NIST Chemistry Reference 2,5-Dimethyl-4-hydroxy-3(2h)-furanone(3658-77-3)
EPA Substance Registry System 4-Hydroxy-2,5-dimethyl-3(2H)furanone (3658-77-3)
UNSPSC Code 85151701
NACRES NA.24

Safety

Hazard Codes :Xn
Risk Statements :22
Safety Statements :36-24/25
WGK Germany :3
RTECS :LU3990000
F :10-23
HS Code :29321900
Hazardous Substances Data :3658-77-3(Hazardous Substances Data)

NFPA 704:

	1
1		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H302-H314-H317
Precautionary statements P260-P270-P280-P301+P312-P303+P361+P353-P305+P351+P338

Furaneol Price More Price(14)

Brand: Sigma-Aldrich(India)
Product number: W317454
Product name : 4-Hydroxy-2,5-dimethyl-3(2H)-furanone
Purity: natural, ≥98%, FG
Packaging: 1SAMPLE-K
Price: ₹6419.23
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: W317454
Product name : 4-Hydroxy-2,5-dimethyl-3(2H)-furanone
Purity: natural, ≥98%, FG
Packaging: 100G
Price: ₹24551.1
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: W317454
Product name : 4-Hydroxy-2,5-dimethyl-3(2H)-furanone
Purity: natural, ≥98%, FG
Packaging: 1KG
Price: ₹127518.5
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: W317410
Product name : 4-Hydroxy-2,5-dimethyl-3(2H)-furanone
Purity: 15 wt. % (in propylene glycol), FG
Packaging: 1KG
Price: ₹8591.4
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: W317410
Product name : 4-Hydroxy-2,5-dimethyl-3(2H)-furanone
Purity: 15 wt. % (in propylene glycol), FG
Packaging: 1SAMPLE-K
Price: ₹9681
Updated: 2022/06/14
Buy: Buy

Furaneol Chemical Properties,Usage,Production

Description Furaneol is a very important aroma chemical and is a key flavoring compound found in many kinds of fruits. It can be chemically formed through different carbohydrates during the Mainlard reaction. It can also be synthesized by yeast, bacteria and plants and play some physiological effects. Study has shown that it can suppress the phosphorylation of cAMP response element binding protein, underlying its potential role as an effective inhibitor of hyperpigmentation. It also has the potential to become an effective antimicrobial agent for human beings.
Chemical Properties 4-Hydroxy-2,5-dimethyl-3(2H)-furanone has a fruity caramel or "burnt pineapple" aroma. May be synthesized from dimethyl- 3,4-dihyroxyfuran-2,5-dicarboxylate.
Chemical Properties Furaneol has a sweet, fruity, strawberry, hot sugar, fruity caramel or “burnt pineapple” aroma.
Chemical Properties Furaneol is a constituent of pineapple and strawberry aroma and is also found in other foods. It forms colorless crystals (mp 77–79°C) with a relatively weak, nonspecific odor. Dilute solutions develop a pineapple, strawberrylike odor.
Chemical Properties white to light yellow crystal powde
Occurrence Reported found in guava, grapes, pineapple, raspberry, strawberry fruit and jam, rye bread, Swiss cheese, boiled beef, beer, cocoa, coffee, tea, filberts, almonds, oatmeal, Arctic bramble, yellow passion fruit, mango, shoyu, fermented soy sauce, litchi, malt and Cape gooseberry.
Uses 2,5-Dimethyl-4-hydroxy-3(2H)-furanone is a component of meat essence composition. 2,5-Dimethyl-4-hydroxy-3(2H)-furanone is used in the flavor and perfume industry due to its sweet strawberry aroma.
Preparation Furaneol can be prepared by cyclization of hexane-2,5-diol-3,4-dione in the presence of an acidic catalyst.The dione is the ozonization product of 2,5- hexynediol, which is obtained by ethynylation of acetaldehyde.
In another process, a dialkyl ??-methyldiglycolate (formed from an alkyl lactate and an alkyl monochloroacetate) is reacted with dialkyl oxalate in the presence of a sodium alkoxide and dimethylformamide. The reaction product is cyclized, alkylated, hydrolyzed, and decarboxylated.In another process, a dialkyl ??-methyldiglycolate (formed from an alkyl lactate and an alkyl monochloroacetate) is reacted with dialkyl oxalate in the presence of a sodium alkoxide and dimethylformamide. The reaction product is cyclized, alkylated, hydrolyzed, and decarboxylated .
Definition ChEBI: A member of the class of furans that is 2,5-dimethylfuran carrying additional oxo and hydroxy groups at positions 3 and 4 respectively. It has been found particularly in strawberries and other such fruits.
Aroma threshold values Detection: 0.03 to 60 ppb; aroma characteristics at 0.1%: sweet, slightly burnt brown caramellic, cotton candy with a savory nuance
Taste threshold values Taste characteristics at 0.10 to 1.0 ppm: sweet caramellic cooked meaty and fruity nuances
Synthesis Reference(s) The Journal of Organic Chemistry, 57, p. 5023, 1992 DOI: 10.1021/jo00044a047
Synthesis, p. 377, 1987
General Description 4-Hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF, DMHF) is a caramel-like smelling compound, identified in Maillard reaction systems based on pentoses by GC-MS and GCMS/MS. Solubility data of DMHF in six different solvents over the temperature range from 283.15K to 313.15K under atmospheric pressure of 0.10 MPa has been examined by dynamic method. Separation of the enantiomers of DMHF by capillary electrophoretic method has been reported. Commercially it is synthesized from L-rhamnose. DMHF has been identified as acidic odorant in Thai premium fish sauce samples by aroma extract dilution analysis (AEDA). It is identified as key aroma compound in the distiller′s grains (DG) from wheat. It is reported as the main flavor compound in strawberries and its biosynthesis has been reported. HDMF has been found in various fruits such as pineapples strawberries and grapes, as well as in beef broth , roasted coffee, bread crust, roasted beef, roasted sesame seeds and stewed beef.
Flammability and Explosibility Not classified
Trade name Furaneol® (Firmenich).
Biochem/physiol Actions Taste at 0.10 to 1.0 ppm
Synthesis From dimethyl-3,4-dihydroxyfuran-2,5-dicarboxylate
References Pickenhagen, Wilhelm, et al. "Estimation of 2,5-dimethyl-4-hydroxy-3(2H)-furanone (FURANEOLA®) in cultivated and wild strawberries, pineapples and mangoes." Journal of the Science of Food & Agriculture 32.11(2010):1132-1134.
Farine, Jean Pierre, et al. "4-Hydroxy-5-methyl-3(2H)-furanone and 4-Hydroxy-2,5-dimethyl-3(2H)-furanone, Two Components of the Male Sex Pheromone of Eurycotis floridana (Walker) (Insecta, Blattidae, Polyzosteriinae)." Bioscience Biotechnology & Biochemistry 57.12(2014):2026-2030.
Schwab, W. "Natural 4-hydroxy-2,5-dimethyl-3(2H)-furanone (Furaneol®). " Molecules 18.6(2013):6936-51.