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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

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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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
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)
F Podebrad et al.
Journal of inherited metabolic disease, 22(2), 107-114 (1999-05-11)
Maple syrup urine disease is an autosomal recessive inherited disorder of branched-chain amino acid metabolism due to deficiency of the branched-chain alpha-keto acid dehydrogenase complex. The disease was originally named after the characteristic sweet aroma, reminiscent of maple syrup, present
Claudine Charpentier et al.
Antonie van Leeuwenhoek, 95(3), 263-273 (2009-02-18)
Fifty-four Saccharomyces cerevisiae strains were isolated from Jura "Vin Jaune" velum and characterized by conventional physiological and molecular tests including ITS RFLP and sequence analysis, karyotyping and inter delta typing. ITS RFLP and sequence revealed a specific group of related
F Peraza-Luna et al.
Journal of agricultural and food chemistry, 49(12), 6012-6019 (2001-12-18)
3-Hydroxy-4,5-dimethyl-2(5H)-furanone (sotolone) and 3-amino-4,5-dimethyl-2(5H)-furanone, the postulated precursor of sotolone, were detected in hairy root cultures of Trigonella foenum-graecum (fenugreek) by GC-MS. The hairy root cultures in both conical flasks and airlift with mesh bioreactors were achieved from hypocotyl of seedling
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