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Merck

40703

Sigma-Aldrich

4-Hydroxy-2,5-dimethyl-3(2H)-furanon

≥99.0% (GC)

Synonym(e):

2,5-Dimethyl-4-hydroxy-3(2H)-furanon, Erdbeerfuranon, Furaneol

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About This Item

Empirische Formel (Hill-System):
C6H8O3
CAS-Nummer:
Molekulargewicht:
128.13
Beilstein:
1281357
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352100
PubChem Substanz-ID:
NACRES:
NA.22

Qualitätsniveau

Assay

≥99.0% (GC)

mp (Schmelzpunkt)

73-77 °C (lit.)
74-83 °C

Lagertemp.

2-8°C

SMILES String

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

InChI

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

InChIKey

INAXVXBDKKUCGI-UHFFFAOYSA-N

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Allgemeine Beschreibung

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.

Piktogramme

CorrosionExclamation mark

Signalwort

Danger

Gefahreneinstufungen

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

Lagerklassenschlüssel

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves


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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
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)
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)
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)

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