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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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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)
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)
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)
Etsuko Sugawara et al.
Bioscience, biotechnology, and biochemistry, 71(7), 1761-1763 (2007-07-10)
The formation of HEMF[2(or 5)-ethyl-5(or 2)-methyl-4-hydroxy-3(2H)-furanone], the aroma component specific to miso and soy sauce, was promoted by cultivating the halo-tolerant yeast, Zygosaccharomyces rouxii, in a medium including the amino-carbonyl reaction products based on ribose and glycine. The glucose concentration
Hyo Jung Kim et al.
Journal of cosmetic science, 59(2), 117-125 (2008-04-15)
In previous studies, 4-hydroxy-5-methyl-3[2H]-furanone (HMF) was shown to have potent antioxidative and antimelanogenic effects, suggesting its potential use as a depigmenting agent. The present study investigated its mechanism of action on murine melanoma B16F10 cells stimulated by theophylline, an activator
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