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

Name
4-Hydroxy-2,5-dimethyl-3(2H)furanone
EINECS 222-908-8
CAS No. 3658-77-3
Article Data10
CAS DataBase
Density 1.249 g/cm³
Solubility 176g/L at 20℃
Melting Point 73-77 °C(lit.)
Formula C₆H₈O₃
Boiling Point 215.5 °C at 760 mmHg
Molecular Weight 128.128
Flash Point 90.5 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 36-24/25
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
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-;
PSA 46.53000
LogP 0.76370

Synthetic route

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

: 3658-77-3
furaneol

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With hydrogenchloride; sodium hydroxide In water	81.4%

: 68786-17-4
ethyl 3,4-dihydroxy-5-methyl-2-furancarboxylate

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

: 3658-77-3
furaneol

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide In water; dimethyl sulfate	76.6%

: 111480-79-6
2,5-bisacetoxyhexane-3,4-dione

: 3658-77-3
furaneol

Conditions

Conditions	Yield
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

Conditions	Yield
With sulfuric acid In methanol for 2h; Heating;	59%

: 3615-41-6
L-Rhamnose

: 3658-77-3
furaneol

Conditions

Conditions	Yield
With sodium dihydrogenphosphate; L-Lysine hydrochloride; sodium hydroxide In water at 110℃; for 0.75h; pH=6.5; Temperature; Concentration;	56.7%

: 137142-62-2
2,5-dihydroxy-4,4,-dibromo-3-hexanone

: 3658-77-3
furaneol

Conditions

Conditions	Yield
With triethylamine In ethanol for 2h; Heating;	49%

: 97805-19-1
(3R,4R)-3,4-dihydroxyhexane-2,5-dione

: 3658-77-3
furaneol

Conditions

Conditions	Yield
With piperidine; acetic acid In water for 168h; Heating;	48%

: 73-34-7, 87-96-7, 488-79-9, 551-63-3, 609-01-8, 643-17-4, 643-18-5, 4164-09-4, 6014-42-2, 6155-36-8, 6189-71-5, 6696-41-9, 6736-43-2, 13224-93-6, 22611-09-2, 28161-49-1, 28161-50-4, 28161-52-6, 45864-36-6, 63814-64-2, 71116-59-1, 71116-61-5, 72598-05-1, 87936-88-7, 87936-89-8, 97466-79-0, 116908-82-8, 120442-60-6, 123484-22-0, 133576-32-6
6-deoxy-L-galactose

: 3658-77-3
furaneol

Conditions

Conditions	Yield
With piperidine; acetic acid In ethanol at 80℃; for 2h;	43%

: rhamnose monohydrate

: 3658-77-3
furaneol

Conditions

Conditions	Yield
With disodium hydrogenphosphate; sodium dihydrogenphosphate; GLUTATHIONE In acetic acid butyl ester at 100℃; for 3h; Reagent/catalyst; Time; Inert atmosphere;	36%

: 34693-15-7
fructose 1,6-diphosphate

: 3658-77-3
furaneol

Conditions

Conditions	Yield
With potassium hydroxide; hydrogen; sodium iodide; palladium on activated charcoal In methanol; water at 90℃; under 3102.9 Torr; for 24h;	28.7%
Multi-step reaction with 3 steps 1: D-lactaldehyde, Aldolase, Triosephosphate isomerase / 60 h / Ambient temperature; pH 7.0, PAN-800 gel 2: 85 percent / H2O / 8 h / 90 °C / pH 1.0 3: piperidine, glacial acetic acid / ethanol / 20 h / 80 °C View Scheme

: 60537-23-7
β-6-deoxy-L-sorbose

: 3658-77-3
furaneol

Conditions

Conditions	Yield
With piperidine; acetic acid In ethanol at 80℃; for 20h; Yield given;

: 470-21-3
6-Deoxy-D-fructose (β form)

: 3658-77-3
furaneol

Conditions

Conditions	Yield
With piperidine; acetic acid In ethanol at 80℃; for 20h; Yield given;

: 50-99-7
D-glucose

: 56-40-6
glycine

A: 67-47-0
5-hydroxymethyl-2-furfuraldehyde

B: 3658-77-3
furaneol

C: 1073-96-7
5-hydroxymaltol

D: 3857-25-8
2-hydroxymethyl-5-methylfuran

Conditions

Conditions	Yield
In water at 95℃; for 120h; Product distribution; other reaction time, other temperature;

...Expand

: 87-72-9, 608-45-7, 608-46-8, 608-47-9, 2460-44-8, 6748-95-4, 6763-34-4, 7261-26-9, 7283-06-9, 7283-07-0, 7296-55-1, 7296-56-2, 7296-58-4, 7296-59-5, 7296-60-8, 7296-61-9, 7296-62-0, 7322-30-7, 10257-31-5, 10257-32-6, 10257-33-7, 10257-34-8, 10257-35-9, 19982-83-3, 20242-88-0, 28697-53-2, 36562-42-2, 41546-41-2, 89299-64-9, 107655-34-5, 115794-06-4, 115794-07-5, 130550-15-1, 130606-21-2
D-Xylose

: 56-41-7
L-alanin

A: 3658-77-3
furaneol

B: 27538-10-9
homofuraneol

Conditions

Conditions	Yield
With phosphate buffer pH 6.0 at 90℃; for 1h;

...Expand

: 87-72-9, 608-45-7, 608-46-8, 608-47-9, 2460-44-8, 6748-95-4, 6763-34-4, 7261-26-9, 7283-06-9, 7283-07-0, 7296-55-1, 7296-56-2, 7296-58-4, 7296-59-5, 7296-60-8, 7296-61-9, 7296-62-0, 7322-30-7, 10257-31-5, 10257-32-6, 10257-33-7, 10257-34-8, 10257-35-9, 19982-83-3, 20242-88-0, 28697-53-2, 36562-42-2, 41546-41-2, 89299-64-9, 107655-34-5, 115794-06-4, 115794-07-5, 130550-15-1, 130606-21-2
D-Xylose

: 3658-77-3
furaneol

Conditions

Conditions	Yield
With phosphate buffer pH 6.0 at 90℃; for 1h;

: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

A: 3658-77-3
furaneol

B: 1073-96-7
5-hydroxymaltol

C: 3188-00-9
2-methyltetrahydrofuran-3-one

D: 600-14-6
2,3-Pentanedione

E: 80-71-7
2-hydroxy-3-methylcyclopent-2-en-1-one

F: 116-09-6
hydroxy-2-propanone

Conditions

Conditions	Yield
With water at 150℃; for 1h; also 2,3-dihydro-3,5-dihydroxy-6(13C)methyl-4(H)-pyran-4-one; var. temp., pH, and time; effect of 2,4-dihydroxy-2,5-dimethyl-3(2H)-furanone;

...Expand

: 87-72-9, 608-45-7, 608-46-8, 608-47-9, 2460-44-8, 6748-95-4, 6763-34-4, 7261-26-9, 7283-06-9, 7283-07-0, 7296-55-1, 7296-56-2, 7296-58-4, 7296-59-5, 7296-60-8, 7296-61-9, 7296-62-0, 7322-30-7, 10257-31-5, 10257-32-6, 10257-33-7, 10257-34-8, 10257-35-9, 19982-83-3, 20242-88-0, 28697-53-2, 36562-42-2, 41546-41-2, 89299-64-9, 107655-34-5, 115794-06-4, 115794-07-5, 130550-15-1, 130606-21-2
D-Xylose

: 56-40-6
glycine

: 3658-77-3
furaneol

Conditions

Conditions	Yield
With phosphate buffer pH 6.0 at 90℃; for 1h;

: 219867-18-2
2,5-dimethyl-4-propionyloxy-3(2H)-furanone

: 3658-77-3
furaneol

Conditions

Conditions	Yield
With Soerensen buffer In water at 30℃; Product distribution; time dependence;

: 2,5-dimethyl-3,4-di(propionyloxy)furan

A: 3658-77-3
furaneol

B: 219867-18-2
2,5-dimethyl-4-propionyloxy-3(2H)-furanone

Conditions

Conditions	Yield
With Soerensen buffer In water at 30℃; Product distribution; time dependence;

: 58-86-6
D-xylose

A: 109-08-0
2-Methylpyrazine

B: 3658-77-3
furaneol

C: 19322-27-1
4-hydroxy-5-methyl-3[2H]-furanone

D: 116-09-6
hydroxy-2-propanone

Conditions

Conditions	Yield
With sodium hydroxide; 2,6-diaminohexanoic acid hydrochloride; potassium hydrogencarbonate In water at 100℃; under 750.06 Torr; for 5h; pH=10; Product distribution; Kinetics; Further Variations:; Reagents; pH-values; Pressures; Condensation; Maillard reaction; Amadori rearrangement;

...Expand

: 73-34-7
L-rhamnose

: 3658-77-3
furaneol

Conditions

Conditions	Yield
With citrate phosphate buffer at 70℃; for 48h; pH=3; Product distribution; Further Variations:; Reagents; pH-values; Reaction partners; effect of Cys and AcCys; degradation;

: 50-99-7
D-glucose

A: 17678-20-5
4-hydroxy-2-(hydroxymethyl)-5-methyl-3(2H)-furanone

B: 3658-77-3
furaneol

C: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

Conditions

Conditions	Yield
With glycine In water for 4h; Maillard reaction; Heating;	A n/a B n/a C 7.1 mg

...Expand

: 2280-44-6
D-Glucose

bovine serum albumin: bovine serum albumin

A: 3658-77-3
furaneol

B: 28564-83-2
2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

C: 19322-27-1
4-hydroxy-5-methyl-3[2H]-furanone

Conditions

Conditions	Yield
In phosphate buffer; water at 37℃; for 2191.5h; pH=7.4; Maillard reaction;

...Expand

: 488-69-7
fructose-1,6-bisphosphate

: 3658-77-3
furaneol

Conditions

Conditions	Yield
With NADPH In various solvent(s) at 30℃; for 30h; pH=7.5; Product distribution; Further Variations:; Reagents; pH-values; Temperatures; cofactor; substrate conc.; reaction time;

: 3658-77-3
furaneol

: 71-36-3
butan-1-ol

: 2,5-dimethyl-4-butoxy-3(2H)-furanone

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 16h; Heating;	90%

: 67-56-1
methanol

: 3658-77-3
furaneol

: 4077-47-8
2,5-dimethyl-4-methoxy-3(2H)-furanone

Conditions

Conditions	Yield
With toluene-4-sulfonic acid for 6h; Heating;	80%

: 3658-77-3
furaneol

: 64-17-5
ethanol

: 2,5-dimethyl-4-ethoxy-3(2H)-furanone

Conditions

Conditions	Yield
With toluene-4-sulfonic acid for 6h; Heating;	80%

: 3658-77-3
furaneol

: 109-92-2
ethyl vinyl ether

: 113190-55-9
2,5-dimethyl-4-[(1'-ethoxy)ethoxy]-3(2H)-furanone

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydrogencarbonate	78.9%

: 3658-77-3
furaneol

: 127-18-4
1,1,2,2-tetrachloroethylene

: 6,6,7,7-tetrachloro-5-hydroxy-1,3-dimethyl-2-oxabicyclo[3.2.0]heptan-4-one

Conditions

Conditions	Yield
In acetonitrile for 14h; Ambient temperature; Irradiation;	57%

: 3658-77-3
furaneol

: 79-01-6
Trichloroethylene

: 6,6,7-trichloro-5-hydroxy-1,3-dimethyl-2-oxabicyclo[3.2.0]heptan-4-one

Conditions

Conditions	Yield
In acetonitrile for 12h; Ambient temperature; Irradiation;	50%

: 3658-77-3
furaneol

: 57-50-1
Sucrose

: 2,5-dimethyl-3(2H)-furanone 4-O-α-D-glucopyranoside

Conditions

Conditions	Yield
With HEPES buffer; sucrose phosphorylase from Leuconostoc mesenteroides at 32℃; for 15h; pH=7.2; transglycosylation;	45%

: 3658-77-3
furaneol

: 920-37-6
2-Chloroacrylonitrile

: (1S,5S,6R)-6-Chloro-5-hydroxy-1,3-dimethyl-4-oxo-2-oxa-bicyclo[3.2.0]heptane-6-carbonitrile

: (1R,5R,6R)-6-Chloro-4,4,5-trihydroxy-1,3-dimethyl-2-oxa-bicyclo[3.2.0]heptane-6-carbonitrile

Conditions

Conditions	Yield
In acetonitrile Irradiation;	A 44% B 6%
With air In acetonitrile Irradiation;	A 44% B 6%

...Expand

: 3658-77-3
furaneol

: 126-98-7
methacrylonitrile

: (1S,5S,6S)-5-Hydroxy-1,3,6-trimethyl-4-oxo-2-oxa-bicyclo[3.2.0]heptane-6-carbonitrile

: (1R,5R,6S)-4,4,5-Trihydroxy-1,3,6-trimethyl-2-oxa-bicyclo[3.2.0]heptane-6-carbonitrile

Conditions

Conditions	Yield
In acetonitrile for 2.5h; Irradiation;	A 41% B 15%
With air In acetonitrile for 2.5h; Irradiation;	A 41% B 15%

...Expand

: 3658-77-3
furaneol

: 111-34-2
-butyl vinyl ether

: 2,5-dimethyl-4-[(1'-butoxy)ethoxy]-3(2H)-furanone

Conditions

Conditions	Yield
	37.8%

: 3658-77-3
furaneol

: 762-42-5
dimethyl acetylenedicarboxylate

: dimethyl 5-hydroxy-1,3-dimethyl-4-oxo-2-oxabicyclo[3.2.0]hept-6-ene-6,7-dicarboxylate

Conditions

Conditions	Yield
In acetonitrile for 6h; Irradiation;	25%

: 3658-77-3
furaneol

: 107-13-1
acrylonitrile

: (1R,5R,6S)-4,4,5-Trihydroxy-1,3-dimethyl-2-oxa-bicyclo[3.2.0]heptane-6-carbonitrile

Conditions

Conditions	Yield
With air In acetonitrile for 2h; Irradiation;	22%

: 3658-77-3
furaneol

: 4753-07-5, 5160-10-1, 14206-57-6, 14227-66-8, 14257-35-3, 42385-75-1, 67650-37-7, 68682-05-3, 69308-57-2, 69349-74-2, 70223-96-0, 70223-97-1, 71276-38-5, 85248-99-3, 118493-15-5, 120575-76-0
2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide

: Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(2,5-dimethyl-4-oxo-4,5-dihydro-furan-3-yloxy)-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

Conditions

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane at 35℃; for 0.75h;	22%

: 3658-77-3
furaneol

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: 121063-57-8
glucofuraneol tetraacetate

Conditions

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane at 35℃; for 0.75h;	19%
With calcium sulfate; silver(l) oxide In dichloromethane

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

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

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

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

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

Reported in EPA TSCA Inventory.

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

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

DOT Classification: 3; Label: Flammable Liquid

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

Product Name

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

Synthetic route

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

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

4-Hydroxy-2,5-dimethyl-3(2H)furanone Toxicity Data With Reference

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

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

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

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

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