3658-77-3 Usage
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
Different sources of media describe the Chemical Properties of 3658-77-3 differently. You can refer to the following data:
1. 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.
2. white to light yellow crystal powde
3. 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.
4. Furaneol has a sweet, fruity, strawberry, hot sugar, fruity caramel or “burnt pineapple” aroma.
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.
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.
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 .
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/jo00044a047Synthesis, 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
Notclassified
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.
Check Digit Verification of cas no
The CAS Registry Mumber 3658-77-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,6,5 and 8 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 3658-77:
(6*3)+(5*6)+(4*5)+(3*8)+(2*7)+(1*7)=113
113 % 10 = 3
So 3658-77-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3-4H,1-2H3/t3-,4?/m1/s1
3658-77-3Relevant articles and documents
Comparison of 2-acetylfuran formation between ribose and glucose in the Maillard reaction
Wang, Yu,Ho, Chi-Tang
body text, p. 11997 - 12001 (2010/03/25)
Sugar type is a major factor regulating the reaction rates and pathways in Maillard reaction. Ribose and glucose were used to compare their reactivities and pathways of 2-acetylfuran formation. A stable isotope labeling method was used to study their reactivity. A 1:1 mixture of [13C 6]glucose and unlabeled ribose (or other unlabeled sugar) was reacted with proline at 145 °C for 40 min. The reactivity of each sugar was revealed by the ratio of isotopomers. The reactivity of sugars in 2-acetylfuran formation decreased in the order ribose, fructose, glucose, rhamnose, and sucrose. This method simplified the reaction system and the calculation process and gave a direct comparison of reactivity as seen via mass spectrum. The difference between glucose and ribose in 2-acetylfuran formation was that glucose could form 2-acetylfuran directly from cyclization of its intact carbon skeleton, whereas ribose first underwent degradation into fragments before forming a six-carbon unit leading to 2-acetylfuran. In the presence of cysteine, ribose could not generate 2-acetylfuran at a detectable level. When ribose was reacted with glycine, formaldehyde generated from glycine combined with ribose to form 2-acetylfuran. In other amino acids, a symmetric structure of the ribose intermediate was formed, making fragmentation more complicated.
Potential of gas chromatography-orthogonal acceleration time-of-flight mass spectrometry (GC-oaTOFMS) in flavor research
Fay, Laurent B.,Newton, Anthony,Simian, Herve,Robert, Fabien,Douce, David,Hancock, Peter,Green, Martin,Blank, Imre
, p. 2708 - 2713 (2007/10/03)
Gas chromatography-orthogonal acceleration time-of-flight mass spectrometry (GC-oaTOFMS) is an emerging technique offering a straightforward access to a resolving power up to 7000. This paper deals with the use of GC-oaTOFMS to identify the flavor components of a complex seafood flavor extract and to quantify furanones formed in model Maillard reactions. A seafood extract was selected as a representative example for complex food flavors and was previously analyzed using GC-quadrupole MS, leaving several molecules unidentified. GC-oaTOFMS analysis was focused on these unknowns to evaluate its potential in flavor research, particularly for determining exact masses, N-Methyldithiodimethylamine, 6-methyl-5-hepten-2-one, and tetrahydro-2,4-dimethyl-4H-pyrrolo- [2,1-d]-1,3,5-dithiazine were successfully identified on the basis of the precise mass determination of their molecular ions and their major fragments. A second set of experiments was performed to test the capabilities of the GC-oaTOFMS for quantification. Calibration curves were found to be linear over a dynamic range of 103 for the quantification of furanones. The quantitative data obtained using GC-oaTOFMS confirmed earlier results that the formation of 4-hydroxy-2,5-dimethyl-3(2H)-furanone was favored in the xylose/glycine model reaction and 2(or 5) -ethyl-4-hydroxy-5(or2)-methyl-3(2H)-furanone in the xylose/alanine model reaction. It was concluded that GC-oaTOFMS may become a powerful analytical tool for the flavor chemist for both identification and quantification purposes, the latter in particular when combined with stable isotope dilution assay.
Formation of Hydroxyfuranone and Hydroxypyranone Derivatives with DNA-Breaking Activity in the Maillard Reaction of Glucose and Albumin under Physiological Conditions
Hiramoto, Kazuyuki,Ishihara, Akira,Sakui, Norihiro,Daishima, Shigeki,Kikugawa, Kiyomi
, p. 101 - 104 (2007/10/03)
Formation of DNA breaking hydroxyfuranone and hydroxypyranone derivatives in the Maillard reaction of glucose and bovine serum albumin (BSA) under physiological conditions was investigated. A mixture of glucose and BSA was incubated at 37 deg C in water or in 1 M phosphate buffer (pH 7.4). The ethyl acetate/2-propanol extract of the reaction mixtures showed significant DNA breaking activity against supercoiled DNA especially in the presence of Fe(III) ion. Gas chromatography/mass spectrometry analysis of the mixture revelaed the formation of DNA breaking hydroxyfuranones (HMF and DMHF) and hydroxypyranone (DDMP).
