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W317403

Sigma-Aldrich

4-Hydroxy-2,5-dimethyl-3(2H)-furanone

≥98%, FCC, FG

Synonym(s):

2,5-Dimethyl-4-hydroxy-3(2H)-furanone, Furaneol, Strawberry furanone

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About This Item

Empirical Formula (Hill Notation):
C6H8O3
CAS Number:
3658-77-3
Molecular Weight:
128.13
FEMA Number:
3174
Beilstein:
1281357
EC Number:
222-908-8
Council of Europe no.:
536
MDL number:
MFCD00010706
UNSPSC Code:
12164502
PubChem Substance ID:
24901514
Flavis number:
13.010
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

FG
Fragrance grade
Halal
Kosher

Agency

follows IFRA guidelines
meets purity specifications of JECFA

reg. compliance

EU Regulation 1223/2009
EU Regulation 1334/2008 & 178/2002
FCC

Assay

≥98%

mp

73-77 °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; strawberry; sweet

storage temp.

2-8°C

SMILES string

CC1OC(C)=C(O)C1=O

InChI

1S/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3

InChI key

INAXVXBDKKUCGI-UHFFFAOYSA-N

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General description

4-Hydroxy-2,5-dimethyl-3(2H)-furanone is a flavor compound that occurs in fruits such as pineapple, strawberry and mango.

Application


  • FaQR, required for the biosynthesis of the strawberry flavor compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone, encodes an enone oxidoreductase.: This study identifies the FaQR gene as essential for the biosynthesis of the key strawberry flavor compound, 4-hydroxy-2,5-dimethyl-3(2H)-furanone. The research highlights the enzymatic pathway involved and its potential applications in biotechnology for flavor enhancement in food products (Raab et al., 2006).

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314,H317

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Estimation of 2, 5?dimethyl?4?hydroxy?3 (2H)?furanone (FURANEOLA?) in cultivated and wild strawberries, pineapples and mangoes
Pickenhagen W, et al.
Journal of the Science of Food and Agriculture, 32(11), 1132-1134 (1981)
A rational synthesis of 4-hydroxy-2, 5-dimethyl-3 (2H)-furanone, a flavor component of pineapple
Henry DW & Silverstein RM.
The Journal of Organic Chemistry, 31(7), 2391-2394 (1966)
Woo Sang Sung et al.
Life sciences, 80(6), 586-591 (2006-11-14)
2,5-Dimethyl-4-hydroxy-3(2H)-furanone (DMHF), an aroma compound found in a number of fruits and foods, has shown various biological properties in animal models, but its antimicrobial effect remains poorly understood. The current study investigated the antimicrobial effect of DMHF using human pathogenic
Xiaofen Du et al.
Journal of chromatography. A, 1208(1-2), 197-201 (2008-09-09)
A GC-MS method for the determination of furaneol in fruit juice was developed using Lichrolut-EN solid-phase extraction (SPE) coupled to microvial insert thermal desorption. Lichrolut-EN can effectively extract furaneol from juice, and had much less retention for pigments and other
Markus Verginer et al.
FEMS microbiology ecology, 74(1), 136-145 (2010-07-29)
Besides its influence on plant growth and health, plant-associated bacteria exert an impact on fruit quality. Methylotrophic bacteria can enhance the biosynthesis of strawberry flavor compounds, especially the two furanoid compounds 2,5-dimethyl-4-hydroxy-2H-furanone (DMHF) and 2,5-dimethyl-4-methoxy-2H-furanone in vitro. Here, we report
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