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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

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

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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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
José Sousa Câmara et al.
Journal of agricultural and food chemistry, 52(22), 6765-6769 (2004-10-28)
The maturation of Madeira wines usually involves exposure to relatively high temperatures and humidity levels >70%, which affect the aroma and flavor composition and lead to the formation of the typical and characteristic bouquet of these wines. To estimate the
Atsushi Taga et al.
Journal of oleo science, 61(1), 45-48 (2011-12-23)
A strongly aromatic compound, sotolon, was assessed by capillary zone electrophoresis within 9 min without specific pre-sample treatment. The calibration curve comprised a straight line with good linearity (R = 0.997) over a relatively wide range of 3.13 to 100
Valérie Lavigne et al.
Journal of agricultural and food chemistry, 56(8), 2688-2693 (2008-04-01)
GC-MS in electron ionization mode (EI) was used as a simple, sensitive method for assaying sotolon [4,5-dimethyl-3-hydroxy-2(5) H-furanone] in various dry white wines. The impact of barrel-aging conditions, that is, whether yeast lees were present or not, on the formation
Alexandre Pons et al.
Journal of agricultural and food chemistry, 56(5), 1606-1610 (2008-02-15)
The enantiomers of sotolon, a flavor compound typical of oxidized white wines, were separated by preparative HPLC to determine their perception thresholds and distribution in wines. The enantiomeric ratios of chiral sotolon were evaluated in several dry white wines using
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