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W363405

Sigma-Aldrich

4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-one

≥97%, FG

Synonym(s):

Caramel furanone, Sotolon, Sugar lactone

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About This Item

Empirical Formula (Hill Notation):
C6H8O3
CAS Number:
28664-35-9
Molecular Weight:
128.13
FEMA Number:
3634
EC Number:
249-136-4
Council of Europe no.:
11834
MDL number:
MFCD00059957
UNSPSC Code:
12164502
PubChem Substance ID:
24901819
Flavis number:
10.030
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

FG
Fragrance grade
Halal
Kosher

Agency

follows IFRA guidelines

reg. compliance

EU Regulation 1223/2009
EU Regulation 1334/2008 & 178/2002
FDA 21 CFR 117

Assay

≥97%

refractive index

n20/D 1.491 (lit.)

bp

184 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

fragrance allergen

no known allergens

Organoleptic

caramel; maple; sweet

SMILES string

CC1OC(=O)C(O)=C1C

InChI

1S/C6H8O3/c1-3-4(2)9-6(8)5(3)7/h4,7H,1-2H3

InChI key

UNYNVICDCJHOPO-UHFFFAOYSA-N

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General description

4,5-Dimethyl-3-hydroxy-2,5-dihydrofuran-2-one is the key aroma and flavor compound of fenugreek seeds. It also occurs wine and tobacco.

Biochem/physiol Actions

Odor at 1.0%
Taste at 5-25 ppm

Other Notes

Natural occurrence: Fenugreek seed, roasted Virginia tobacco and rice wine.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SHBP1032
STBK0744
STBJ9271
STBH5023
STBH3764

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Fenugreek lactone attenuates palmitate-induced apoptosis and dysfunction in pancreatic ?-cells
Gong J, et al.
Journal of the American Society of Brewing Chemists, 21(48), 13457-13457 (2015)
T König et al.
Journal of agricultural and food chemistry, 47(8), 3288-3291 (1999-12-20)
Gas chromatography/olfactometry (GCO) and gas chromatography-mass spectrometry (HRGC-MS) revealed 3-hydroxy-4, 5-dimethyl-2(5H)-furanone (sotolon) to be responsible for the "burnt" and "spicy" off-flavor observed in citrus soft drinks during storage. Among the ingredients of citrus soft drinks, ethanol and ascorbic acid were
An overview of the effects of tobacco ingredients on smoke chemistry and toxicity.
Baker RR, et al.
Food And Chemical Toxicology, 42, 53-83 (2004)
Alexandre Pons et al.
Journal of agricultural and food chemistry, 58(12), 7273-7279 (2010-05-22)
Sotolon (3-hydroxy-4,5-dimethyl-2(5H)-furanone) is a chiral furanone, an aroma compound known to be responsible for premature-aging flavor in dry white wines. Sotolon generally results from mild oxygenation during bottle aging, and until now, its formation pathways had not been elucidated. The
Raquel M Callejón et al.
Journal of agricultural and food chemistry, 56(15), 6631-6639 (2008-07-12)
Two gas chromatography-olfactometry (GC-O) techniques were used to screen targeting compounds with an impact on the perceived quality of Sherry vinegar: detection frequency and aroma extract dilution analysis (AEDA). The GC-O study revealed the presence of 108 aromatic notes, of
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