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W363501

Sigma-Aldrich

4-Hydroxy-5-methyl-3-furanone

97%, FG

Synonym(s):

toffee furanone

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About This Item

Linear Formula:
C4OH2OCH3OH
CAS Number:
19322-27-1
Molecular Weight:
114.10
FEMA Number:
3635
EC Number:
242-961-0
MDL number:
MFCD02752619
UNSPSC Code:
12164502
PubChem Substance ID:
24901822
Flavis number:
13.085
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

FG
Halal
Kosher

reg. compliance

EU Regulation 1334/2008 & 872/2012
FDA 21 CFR 110

Assay

97%

mp

129-133 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

Organoleptic

caramel; coffee; brown; sweet

SMILES string

CC1=C(O)C(=O)CO1

InChI

1S/C5H6O3/c1-3-5(7)4(6)2-8-3/h7H,2H2,1H3

InChI key

DLVYTANECMRFGX-UHFFFAOYSA-N

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General description

4-Hydroxy-5-methyl-3-furanone is the key flavor component of beef broth and shoyu (soy sauce).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Components contributing to beef flavor. Isolation of 4-hydroxy-5-methyl-3 (2H)-furanone and its 2, 5-dimethyl homolog from beef broth
Tonsbeek CH, et al.
Journal of Agricultural and Food Chemistry, 16(6), 1016-1021 (1968)
Mechanism of formation of 4-hydroxy-5-methyl-3 (2H)-furanone, a component of beef flavor, from Amadori products.
Hicks KB & Feather MS.
Journal of Agricultural and Food Chemistry, 23(5), 957-960 (1975)
Production of 4-hydroxy-5-methyl-3 (2H)-furanone, a component of beef flavor, from a 1-amino-1-deoxy-D-fructuronic acid
Hicks KB, et al.
Journal of Agricultural and Food Chemistry, 22(4), 724-725 (1974)
Isolation of 4-hydroxy-5-methyl-3 (2H)-furanone, a flavor component in shoyu (soy sauce).
Nunomura N, et al.
Agricultural and Biological Chemistry, 43(6), 1361-1363 (1979)
F B Whitfield et al.
Journal of agricultural and food chemistry, 47(4), 1626-1634 (1999-11-24)
Reaction of 4-hydroxy-5-methyl-3(2H)-furanone (HMF) with cysteine or hydrogen sulfide at pH 4.5 for 60 min at 140 degrees C produced complex mixtures of volatile compounds, the majority of which contained sulfur. Sixty-nine compounds were identified, some tentatively, by GC/MS. These
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