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40703

Sigma-Aldrich

4-Hydroxy-2,5-diméthyl-3(2H)-furanone

≥99.0% (GC)

Synonyme(s) :

2,5-Diméthyl-4-hydroxy-3(2H)-furanone, Furanone de fraise, Furanéol

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About This Item

Formule empirique (notation de Hill):
C6H8O3
Numéro CAS:
3658-77-3
Poids moléculaire :
128.13
Numéro Beilstein :
1281357
Numéro CE :
222-908-8
Numéro MDL:
MFCD00010706
Code UNSPSC :
12352100
ID de substance PubChem :
57650013
Nomenclature NACRES :
NA.22

Pureté

≥99.0% (GC)

Pf

73-77 °C (lit.)
74-83 °C

Température de stockage

2-8°C

Chaîne SMILES 

CC1OC(C)=C(O)C1=O

InChI

1S/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3

Clé InChI

INAXVXBDKKUCGI-UHFFFAOYSA-N

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Catégories apparentées

Description générale

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.

Pictogrammes

CorrosionExclamation mark
GHS05,GHS07

Mention d'avertissement

Danger

Mentions de danger

H302,H314,H317

Classification des risques

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1

Code de la classe de stockage

8A - Combustible corrosive hazardous materials

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
BCBT0290
BCBH1651V
BCBC1549V
BCBC1549
1360923

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Consulter la Bibliothèque de documents

Capillary electrophoretic resolution of the enantiomers of 2,5-dimethyl-4-hydroxy-3(2H)-furanone, the key flavor compounds in strawberry fruit.
Raab T, et al.
Chromatographia, 57(7-8), 501-504 (2003)
Formation of 4-hydroxy-2, 5-dimethyl-3 (2 H)-furanone and 4-hydroxy-2 (or 5)-ethyl-5 (or 2)-methyl-3 (2 H)-furanone through Maillard reaction based on pentose sugars.
Blank I and Fay LB.
Journal of Agricultural and Food Chemistry, 44(2), 531-536 (1996)
Experimental determination and correlation of the solubility of 4-hydroxy-2, 5-dimethyl-3(2H)-furanone (DMHF) in six different solvents.
Zhu L, et al.
The Journal of Chemical Thermodynamics, 91, 369-377 (2015)
M Roth et al.
Journal of agricultural and food chemistry, 62(45), 10873-10880 (2014-09-23)
The limited use of distiller's grains (DG) in the food industry depends occasionally on the characteristic odor of DG. For a better understanding of this typical odor, a sensory evaluation was performed first. The impressions seasoninglike, roasty/breadlike, and malty/caramellike were
Tobias Hauck et al.
Carbohydrate research, 337(13), 1185-1191 (2002-07-12)
The selective chemical formation of 4-hydroxy-2,5-dimethyl-3[2H]-furanone (HDF) from D-fructose 1,6-diphosphate in the presence of reduced nicotinamide-adenine-dinucleotides (NAD(P)H) was investigated by means of HPLC-DAD and HPLC-UV-MS/MS. The temperature optimum for HDF formation was 30 degrees C, whereas the pH value (pH
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