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3658-77-3

Basic Information
CAS No.: 3658-77-3
Name: 4-Hydroxy-2,5-dimethyl-3(2H)furanone
Article Data: 10
Molecular Structure:
Molecular Structure of 3658-77-3 (4-Hydroxy-2,5-dimethyl-3(2H)furanone)
Formula: C6H8O3
Molecular Weight: 128.128
Synonyms: 2,5-Dimethyl-3-hydroxy-4-oxo-4,5-dihydrofuran;2,5-Dimethyl-4,5-dihydrofuran-3-ol-4-one;2,5-Dimethyl-4-hydroxy-2,3-dihydrofuran-3-one;2,5-Dimethyl-4-hydroxy-3(2H)-furanone;4-Hydroxy-2,5-Dimethyl-3-oxo-2,3-dihydrofuran;4-Hydroxy-2,5-dimethyl-2,3-dihydrofuran-3-one;4-Hydroxy-2,5-dimethyl-2H-furan-3-one;Alletone;Furaneol;Pineapple ketone;3(2H)-Furanone,4-hydroxy-2,5-dimethyl-;
EINECS: 222-908-8
Density: 1.249 g/cm3
Melting Point: 73-77 °C(lit.)
Boiling Point: 215.5 °C at 760 mmHg
Flash Point: 90.5 °C
Solubility: 176g/L at 20℃
Appearance: white to light yellow crystal powder
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 36-24/25
PSA: 46.53000
LogP: 0.76370
Synthetic route

sodium 2,5-dimethyl-2,5-dihydrofuran-2,3,4-triolate

3658-77-3

furaneol

Conditions
ConditionsYield
With sulfuric acid at 10 - 20℃; for 1h; Reagent/catalyst;96.3%
121063-57-8

glucofuraneol tetraacetate

A

3658-77-3

furaneol

B

121063-56-7

2,5-dimethyl-4-hydroxy-3<2H>-furanone β-D-glucopyranoside

Conditions
ConditionsYield
With sodium methylate In methanol for 4h; Ambient temperature;A 8%
B 92%
25566-16-9

hexane-3,4-cis-diol-2,5-dione

3658-77-3

furaneol

Conditions
ConditionsYield
With sodium phosphate dibasic dodecahydrate; phosphoric acid In acetic acid butyl ester; water at 70 - 80℃; for 0.833333h; Reagent/catalyst; Flow reactor;86%
With disodium hydrogenphosphate; sodium hydrogencarbonate In water; ethyl acetate at 75℃; for 36h; pH=7; pH-value; Solvent; Temperature; Inert atmosphere;6.8 g
488-79-9

6-deoxy-D-glucose

3658-77-3

furaneol

Conditions
ConditionsYield
With piperidine; acetic acid In ethanol at 80℃; for 24h;85%
Multi-step reaction with 3 steps
1: 90 percent / NaBH4 / H2O / 0.5 h / Ambient temperature
2: 95 percent / sorbitol dehydrogenase (SDH), NAD, α-ketoglutarate monosodium salt, (NH4)2SO4, GluDH / H2O / 10 h / pH 8.2
3: piperidine, glacial acetic acid / ethanol / 20 h / 80 °C
View Scheme

3,4-hexanedione-2,5-diyl bis(tert-butyl carbonate)

3658-77-3

furaneol

Conditions
ConditionsYield
With oxalic acid for 5h; Heating;85%
74-83-9

methyl bromide

68786-17-4

ethyl 3,4-dihydroxy-5-methyl-2-furancarboxylate

3658-77-3

furaneol

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In water81.4%
68786-17-4

ethyl 3,4-dihydroxy-5-methyl-2-furancarboxylate

methyl 5-methyl-3,4-dihydroxy-2-furoate

3658-77-3

furaneol

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In water; dimethyl sulfate76.6%
111480-79-6

2,5-bisacetoxyhexane-3,4-dione

3658-77-3

furaneol

Conditions
ConditionsYield
With oxalic acid In water for 3.2h; Heating;66%
80037-18-9

2,2'-Dimethoxy-3,3'-dimethyl-[2,2']bioxiranyl

3658-77-3

furaneol

Conditions
ConditionsYield
With sulfuric acid In methanol for 2h; Heating;59%
3615-41-6

L-Rhamnose

3658-77-3

furaneol

Conditions
ConditionsYield
With sodium dihydrogenphosphate; L-Lysine hydrochloride; sodium hydroxide In water at 110℃; for 0.75h; pH=6.5; Temperature; Concentration;56.7%
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    Product name:4-Hydroxy-2,5-Dimethyl-3(2H)Furanone CAS No.: 3658-77-3 Molecule Formula:C6H8O3 Molecule Weight:128.13 Purity: 99.0% Package: 25kg/drum Description:Whiteto light yellow crystalline powder Manufacture Standards:Enterprise

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Chemistry

Molecular Structure of 4-Hydroxy-2,5-dimethyl-3(2H)furanone (CAS NO.3658-77-3):

IUPAC Name: 4-Hydroxy-2,5-dimethylfuran-3-one
Canonical SMILES: CC1C(=O)C(=C(O1)C)O
InChI: InChI=1S/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3
InChIKey: INAXVXBDKKUCGI-UHFFFAOYSA-N
Molecular Weight: 128.12592 [g/mol]
Molecular Formula: C6H8O3
XLogP3-AA: 0.7
H-Bond Donor: 1
H-Bond Acceptor: 3 
EINECS: 222-908-8 
storage temp.: 2-8 °C 
Index of Refraction: 1.512
Molar Refractivity: 30.78 cm3
Molar Volume: 102.5 cm3
Surface Tension: 42.2 dyne/cm
Density: 1.249 g/cm3
Flash Point: 90.5 °C
Enthalpy of Vaporization: 52.55 kJ/mol
Boiling Point: 215.5 °C at 760 mmHg
Vapour Pressure: 0.032 mmHg at 25 °C
Appearance: white to light yellow crystal powder
Melting Point: 73-77 °C(lit.)
Classification Code: Mutation data 
Product Categories: Furan&Benzofuran; API intermediates; Alphabetical Listings; C-D; Flavors and Fragrances; Furan flavors

Uses

 4-Hydroxy-2,5-dimethyl-3(2H)furanone (CAS NO.3658-77-3) is used as flavorant in the lields of food,beverage and daily-use chemical industry.

Toxicity Data With Reference

1.    

mmo-sat 2 mg/plate

    CHYCDW    Zhonghua Yufangyixue Zazhi. Chinese Journal of Preventive Medicine. 22 (1988),85.
2.    

sce-mus-ipr 186 mg/kg

    CHYCDW    Zhonghua Yufangyixue Zazhi. Chinese Journal of Preventive Medicine. 22 (1988),85.
3.    

orl-mus LD50:1608 mg/kg

    CHYCDW    Zhonghua Yufangyixue Zazhi. Chinese Journal of Preventive Medicine. 22 (1988),85.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Safety Information of 4-Hydroxy-2,5-dimethyl-3(2H)furanone (CAS NO.3658-77-3):
Hazard Codes:Xn 
Risk Statements:22
22:Harmful if swallowed 
Safety Statements:36-24/25
36:Wear suitable protective clothing
24/25:Avoid contact with skin and eyes   
WGK Germany:3
RTECS:LU3990000
F:10-23
Moderately toxic by ingestion. Mutation data reported. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating vapors.

Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid

Specification

 4-Hydroxy-2,5-dimethyl-3(2H)furanone (CAS NO.3658-77-3), its Synonyms are 2,5-Dimethyl-3-hydroxy-4-oxo-4,5-dihydrofuran ; 2,5-Dimethyl-4-hydroxy-2,3-dihydrofuran-3-one ; 2,5-Dimethyl-4-hydroxy-3(2H)-furanone ; 3(2H)-Furanone, 4-hydroxy-2,5-dimethyl- ; Alletone ; FEMA No. 3174 ; Furaneol ; Pineapple ketone ; 3(2H)-Furanone, 2,5-dimethyl-4-hydroxy- ; 4-Hydroxy-2,5-dimethylfuran-2(3H)-one .