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Merck

W363405

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
Council of Europe no.:
11834
UNSPSC Code:
12164502
PubChem Substance ID:
24901819
Flavis number:
10.030
EC Number:
249-136-4
NACRES:
NA.21
MDL number:
MFCD00059957
Organoleptic:
caramel; maple; sweet
Grade:
FG, Fragrance grade, Halal, Kosher
Biological source:
synthetic
Agency:
follows IFRA guidelines
Food allergen:
no known allergens

Key Documents

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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

biological source

synthetic

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

Quality Level

300, 400

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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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SHBT5906
SHBT0765
SHBQ3354
SHBP9545
SHBP1032

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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)
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
False diagnosis of maple syrup urine disease owing to ingestion of herbal tea.
A C Sewell et al.
The New England journal of medicine, 341(10), 769-769 (1999-09-04)
A F Pisarnitskiĭ et al.
Prikladnaia biokhimiia i mikrobiologiia, 23(5), 642-646 (1987-09-01)
The mechanism of formation of 4,5-dimethyl-3-hydroxy-2/5H/-furanone in some food-stuffs was investigated. The compound was found to result from condensation of acetaldehyde under oxidative conditions. The intermediate product of the condensation is 2-oxobutanoic acid.
Paula Vanessa Guerra et al.
Journal of agricultural and food chemistry, 59(9), 4699-4704 (2011-03-23)
4,5-Dimethyl-3-hydroxy-2(5H)-furanone (sotolone), a naturally occurring flavor impact compound, can be isolated from various sources, especially fenugreek seeds. It can also be thermally produced from intermediates generated from the Maillard reaction such as pyruvic and ketoglutaric acids, glyoxal, and 2,3-butanedione. A
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