Conditions | Yield |
---|---|
With sodium sulfate In water at 26℃; for 3h; Temperature; Time; Concentration; | A 88.5% B 99.8% |
C15H26O3Si
Maltol
Conditions | Yield |
---|---|
With potassium acetate In water; N,N-dimethyl-formamide at 25℃; for 20h; | 92% |
3-((tert-butyldimethylsilyl)oxy)-2-methyl-4H-pyran-4-one
Maltol
Conditions | Yield |
---|---|
With lithium acetate In water; N,N-dimethyl-formamide at 25℃; for 8h; Inert atmosphere; | 90% |
Maltol
Conditions | Yield |
---|---|
With sodium hydroxide In water at -5 - 30℃; pH=2 - 3; | 80.5% |
Conditions | Yield |
---|---|
With tert-butylhypochlorite In acetic acid 1.) 25 deg C, 2 h, 2.) 90 deg C, 4 h; | 75% |
With chlorine In methanol; water 1.) -5 deg C; 2.) 90-95 deg C, 3.5 h; | 71% |
With chlorine In methanol; water at 90 - 95℃; for 3.5h; Rearrangement; | 71% |
4,6-dimethoxy-2-methyl-2H-pyran-3(6H)-one
Maltol
Conditions | Yield |
---|---|
With sulfuric acid at 25℃; for 0.333333h; | 74% |
2-(1-hydroxyethyl)-2,3,5-trimethoxy-2,5-dihydrofuran
Maltol
Conditions | Yield |
---|---|
With sulfuric acid at 25℃; for 4h; | 67% |
In sulfuric acid | 67% |
Multi-step reaction with 2 steps 1: 77 percent / formic acid / methanol / 0.17 h / 20 °C 2: 74 percent / 2M aq. H2SO4 / 0.33 h / 25 °C View Scheme |
trans-4-chloro-6-methoxy-2-methyl-2H-pyran-3(6H)-one
Maltol
Conditions | Yield |
---|---|
With acetic acid for 1.5h; Heating; | 66% |
4-chloro-6-methoxy-2-methyl-2H-pyran-3(6H)-one
Maltol
Conditions | Yield |
---|---|
With acetic acid | 65% |
6-methoxy-2-methyl-2H-pyran-3(6H)-one
Maltol
Conditions | Yield |
---|---|
With chlorine In acetic acid 1.) 10 deg C, 30 min; 2.) reflux 1.5 h; | 56% |
With sodium hydroxide; chlorine In water; acetic acid | 56% |
Multi-step reaction with 2 steps 1: Cl2, triethylamine / CH2Cl2 / 1.) -10 deg C, 30 min; 2.) 10 deg C, 25 min 2: 66 percent / acetic acid / 1.5 h / Heating View Scheme |
Conditions | Yield |
---|---|
With sodium bromide; chlorine In tetrahydrofuran; water | A 55% B n/a |
4-bromo-6-hydroxy-2-methyl-2H-pyran-3(6H)-one
Maltol
Conditions | Yield |
---|---|
In phosphoric acid | 34% |
6-ethoxy-4,5-epoxy-3-oxo-2-methyltetrahydropyran
Maltol
Conditions | Yield |
---|---|
In water | 9.5% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 1h; Ambient temperature; | 60 mg |
3-(β-D-glucopyranosyloxy)-2-methyl-4H-pyran-4-one
Maltol
Conditions | Yield |
---|---|
With hydrogenchloride | 6 mg |
With almond β-glucosidase at 37℃; for 1h; pH=7.5; aq. buffer; Enzymatic reaction; |
Conditions | Yield |
---|---|
With hydrogenchloride for 1h; Heating; |
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; water at 4℃; | A 4.4 mg B 57.4 mg |
4-(α-D-glocopyranosyloxy)-2-hydroxy-2-methyl-2H-pyran-3(6H)-one
A
Maltol
B
β-D-glucose
Conditions | Yield |
---|---|
enzymic hydrolysis; |
1-(N-L-triptophanyl)-1-deoxy-D-fructose
A
5-hydroxymethyl-2-furfuraldehyde
B
Maltol
C
isomaltol
D
α-carboline
E
L-Tryptophan
Conditions | Yield |
---|---|
In water at 95℃; under 750.06 - 450036 Torr; Rate constant; Product distribution; various pressure; ΔV*; |
thymidine diphosphate 4-keto-6-deoxy-α-D-glucose
Maltol
Conditions | Yield |
---|---|
With potassium phosphate buffer for 0.333333h; pH=3.6; Decomposition; |
Conditions | Yield |
---|---|
With air at 400 - 450℃; Oxidation; Formation of xenobiotics; |
Maltol
Conditions | Yield |
---|---|
Decomposition; Formation of xenobiotics; pyrolysis; |
Maltol
Conditions | Yield |
---|---|
With lithium perchlorate; potassium carbonate In acetonitrile for 1.5h; Electrolysis; Hg cathode, Pt anode, -1.0 V (vs SCE); |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 75 percent / NaHCO3, Br2 / methanol / 1.) -30 deg C; 2.) room temp., 2 h 2: 100 percent / NaBH4 / methanol / 15 - 25 °C 3: 67 percent / H2SO4 / 4 h / 25 °C View Scheme | |
Multi-step reaction with 4 steps 1: 75 percent / NaHCO3, Br2 / methanol / 1.) -30 deg C; 2.) room temp., 2 h 2: 100 percent / NaBH4 / methanol / 15 - 25 °C 3: 77 percent / formic acid / methanol / 0.17 h / 20 °C 4: 74 percent / 2M aq. H2SO4 / 0.33 h / 25 °C View Scheme |
2-acetyl-2,3,5-trimethoxy-2,5-dihydrofuran
Maltol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 100 percent / NaBH4 / methanol / 15 - 25 °C 2: 67 percent / H2SO4 / 4 h / 25 °C View Scheme | |
Multi-step reaction with 3 steps 1: 100 percent / NaBH4 / methanol / 15 - 25 °C 2: 77 percent / formic acid / methanol / 0.17 h / 20 °C 3: 74 percent / 2M aq. H2SO4 / 0.33 h / 25 °C View Scheme |
2-methoxy-3,4-dichloro-6-methyl tetrahydropyran-5-one
Maltol
Conditions | Yield |
---|---|
With sodium hydroxide In sulfuric acid |
Conditions | Yield |
---|---|
In tetrahydrofuran; BrCl; water |
Conditions | Yield |
---|---|
In tetrahydrofuran; water; chlorine |
Maltol
Conditions | Yield |
---|---|
With chlorine In methanol; water |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1.25h; Inert atmosphere; | 100% |
Stage #1: Maltol; benzyl bromide In N,N-dimethyl-formamide at 80℃; for 0.25h; Stage #2: With potassium carbonate In N,N-dimethyl-formamide for 1h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 5h; Reflux; | 99.4% |
With potassium carbonate In methanol for 1h; Reflux; | 98% |
With sodium hydroxide In methanol Heating / reflux; | 95% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 3h; Reflux; | 99.4% |
With potassium carbonate In acetone for 6h; Reflux; | 99% |
With potassium carbonate In acetone for 3h; Reflux; | 99.4% |
Maltol
tert-butyldimethylsilyl chloride
3-((tert-butyldimethylsilyl)oxy)-2-methyl-4H-pyran-4-one
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0℃; Inert atmosphere; | 99% |
With 1H-imidazole In dichloromethane at 23℃; for 2h; Inert atmosphere; | 99% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
In dichloromethane suspn. Ru colmplex and maltol in CH2Cl2 was refluxed for 4 h; soln. was kept at -15°C for 7 days, ppt. was filtered off, washedwith n-hexane and dried in vacuo; elem. anal.; | 99% |
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 23℃; for 1.5h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 12h; Reflux; | 99% |
With potassium carbonate In acetone for 6h; Reflux; | 97% |
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 5h; | 65% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 6h; Reflux; | 99% |
Conditions | Yield |
---|---|
at 90℃; for 6h; | 98% |
With acetic acid at 80℃; for 18h; Inert atmosphere; | 84% |
With sodium acetate In chloroform at 125℃; under 2250.2 Torr; for 0.25h; Irradiation; | 75% |
at 80℃; for 6h; |
Maltol
Conditions | Yield |
---|---|
With (C2H5)3N In methanol; dichloromethane (C2H5)3N added to a soln. of Co complex, a soln. of ligand in MeOH added, stirred at room temp. under N2; evapd. (vac.), dissolved in C6H6, filtered, crystd. by diffusion of the soln. with pentane; elem. anal.; | 98% |
Maltol
vanadium(V) oxytriisopropoxide
(malt)2V(V)(O)(O(i)Pr)
Conditions | Yield |
---|---|
In acetonitrile at -20 - 20℃; | 98% |
Conditions | Yield |
---|---|
In ethanol at 100℃; for 6h; Temperature; | 97.02% |
Conditions | Yield |
---|---|
With triethylamine In ethanol; triethylamine; acetonitrile byproducts: NEt3*HNO3; a soln. of γ-pyranone in Et3N and EtOH were added dropwise under N2 to a soln. of AgNO3 in MeCN-EtOH in the dark at 25°C, the mixt.was stirred for 2 h; filtd., ppt. was washed with cold EtOH, filtrate evapd. under vac.; elem. anal.; | 97% |
Conditions | Yield |
---|---|
In methanol at 64℃; for 1h; | 97% |
Maltol
salicylic acid
3-hydroxy-2-methyl-4-pyrone/salicylic acid 1:1 cocrystals
Conditions | Yield |
---|---|
In methanol at 64℃; for 1h; | 97% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 0.166667h; | 97% |
Maltol
oxotribromobis(triphenylphosphine)rhenium(V)
Conditions | Yield |
---|---|
In dichloromethane suspn. Ru colmplex and maltol in CH2Cl2 was refluxed for 4 h; soln. was kept at -15°C for 7 days, ppt. was filtered off, washedwith n-hexane and dried in vacuo; elem. anal.; | 96% |
Conditions | Yield |
---|---|
In methanol at 64℃; for 1h; | 96% |
Conditions | Yield |
---|---|
In methanol for 1h; Reflux; | 96% |
Maltol
3-hydroxy-2-methylpyrid-4-one
Conditions | Yield |
---|---|
Stage #1: Maltol With ammonium hydroxide at 40℃; for 2h; Stage #2: With ammonium carbonate at 40℃; for 10h; Reagent/catalyst; Temperature; Reflux; | 95.7% |
With ammonia In water for 10h; Reflux; | 85% |
With ammonia In water for 10h; Reflux; | 79% |
Maltol
3-O-benzylmaltol
Conditions | Yield |
---|---|
by a literature procedure; | 95% |
Maltol
Conditions | Yield |
---|---|
Stage #1: Maltol With sodium hydroxide In water pH=11.6 - 13.5; Stage #2: With iron(III) chloride In water pH=7.1; Product distribution / selectivity; | 95% |
With ferric citrate; sodium carbonate In water at 20℃; pH=~ 9 - 11.6; Product distribution / selectivity; | |
With iron(II) gluconate; potassium hydroxide In water at 20℃; pH=~ 9 - 11.6; Product distribution / selectivity; Heating / reflux; | |
With sodium hydroxide; sodium iron(II) citrate In water Product distribution / selectivity; | |
With sodium hydroxide; sodium ferric citrate In water at 20℃; pH=~ 9 - 11.6; Product distribution / selectivity; |
Conditions | Yield |
---|---|
In toluene; acetonitrile Electrolysis; electrochemical oxidation of Sn (anode metal) in a CH3CN:toluene (1:1) soln. containing Et4NClO4 of 3-hydroxy-2-methyl-4-pyrone over a period of 1-2 h under N2; filtn., reducing of volume of soln., cooling, drying in vac., washing of yellow solid (EtOH), elem. anal.; | 95% |
Maltol
LACTIC ACID
3-hydroxy-2-methyl-4-pyrone/lactic acid 1:1 cocrystals
Conditions | Yield |
---|---|
In methanol at 64℃; for 1h; | 95% |
Conditions | Yield |
---|---|
In dichloromethane for 4h; Reflux; Inert atmosphere; | 95% |
In dichloromethane for 4h; Reflux; | 54% |
Maltol
chloromethyl methyl ether
3-Methoxymethoxy-2-methyl-pyran-4-one
Conditions | Yield |
---|---|
With diisopropylamine Ambient temperature; | 94% |
Conditions | Yield |
---|---|
tetra(n-butyl)ammonium hydroxide In dichloromethane; water Etherification; Heating; | 94% |
Stage #1: Maltol With tetra(n-butyl)ammonium hydroxide In water at 20℃; for 1h; Stage #2: 5-(chloromethyl)-1,2,3-trimethoxybenzene In dichloromethane for 24h; Heating; |
Conditions | Yield |
---|---|
In methanol for 1h; Reflux; | 94% |
Conditions | Yield |
---|---|
In methanol at 64℃; for 1h; | 93% |
The 3-Hydroxy-2-methyl-4-pyrone, with the CAS registry number 118-71-8 and EINECS registry number 204-271-8, has the systematic name of 3-hydroxy-2-methyl-4H-pyran-4-one. It is a kind of White crystalline powder with a fragrant caramel-butterscotch odor, and belongs to following the proudct categories: Food & Feed Additives; Heterocycles; Food & Flavor Additives. It can be found in the bark of larch tree, in pine needles, and in roasted malt and so on.isolated from Passiflora incarnata; possesses depressant properties in mice; potentiates hexobarbital-induced narcosis & inhibits spontaneous motor activity. It is soluble in hot water, chloroform, and other polar solvents. And the molecular formula of this chemical is C6H6O3.
The physical properties of 3-Hydroxy-2-methyl-4-pyrone are as followings:
(1)ACD/LogP: 0.07; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.07; (4)ACD/LogD (pH 7.4): 0.029; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 25.982; (8)ACD/KOC (pH 7.4): 23.677; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 46.53 Å2; (13)Index of Refraction: 1.561; (14)Molar Refractivity: 30.292 cm3; (15)Molar Volume: 93.546 cm3; (16)Polarizability: 12.009×10-24cm3; (17)Surface Tension: 51.792 dyne/cm; (18)Density: 1.348 g/cm3; (19)Flash Point: 127.32 °C; (20)Enthalpy of Vaporization: 60.778 kJ/mol; (21)Boiling Point: 284.7 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
Preparation of 3-Hydroxy-2-methyl-4-pyrone:
(1) It can be extracted from natural products, because it is a naturally occurring organic compound; (2)It can be prepared by pyromucic aldehyde; (3)Semi-synthesis: It can be prepared by kojic acid, and after a series of oxidation, decarboxylation, formaldehyde reaction, reduction, distillation and recrystallization, you can get the product.
Uses of 3-Hydroxy-2-methyl-4-pyrone:
It is a fragrance molecule used in flavor enhancers and fragrances.usually used as a flavor enhancer. It is also used to impart a sweet aroma to fragrances because of its odor of cotton candy and caramel.
Safety Information of 3-Hydroxy-2-methyl-4-pyrone:
You should be cautious while dealing with 3-Hydroxy-2-methyl-4-pyrone. It irritates to eyes, respiratory system and skin, and it is also harmful if swallowed. Therefore, you had better take the following instructions: Wear suitable gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: Cc1c(c(=O)cco1)O;
(2)InChI: InChI=1/C6H6O3/c1-4-6(8)5(7)2-3-9-4/h2-3,8H,1H3;
(3)InChIKey: XPCTZQVDEJYUGT-UHFFFAOYAH.
The toxicity data of 3-Hydroxy-2-methyl-4-pyrone is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
chicken | LD50 | oral | 3720mg/kg (3720mg/kg) | Toxicology and Applied Pharmacology. Vol. 15, Pg. 604, 1969. | |
guinea pig | LD50 | oral | 1410mg/kg (1410mg/kg) | Dow Chemical Company Reports. Vol. -, Pg. -, 1967. | |
mouse | LD16 | intraperitoneal | 1400mg/kg (1400mg/kg) | Russian Pharmacology and Toxicology Vol. 38, Pg. 213, 1975. | |
mouse | LD50 | oral | 550mg/kg (550mg/kg) | FAO Nutrition Meetings Report Series. Vol. 44A, Pg. 56, 1967. | |
mouse | LD50 | subcutaneous | 820mg/kg (820mg/kg) | Chemical and Pharmaceutical Bulletin. Vol. 22, Pg. 1008, 1974. | |
rabbit | LD | skin | > 5gm/kg (5000mg/kg) | Food and Cosmetics Toxicology. Vol. 13, Pg. 841, 1975. | |
rabbit | LD50 | oral | 1620mg/kg (1620mg/kg) | Dow Chemical Company Reports. Vol. -, Pg. -, 1967. | |
rat | LD50 | oral | 1410mg/kg (1410mg/kg) | FAO Nutrition Meetings Report Series. Vol. 44A, Pg. 56, 1967. |
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