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118-71-8

Basic Information
CAS No.: 118-71-8
Name: 3-Hydroxy-2-methyl-4-pyrone
Article Data: 49
Cas Database
Molecular Structure:
Molecular Structure of 118-71-8 (3-Hydroxy-2-methyl-4-pyrone)
Formula: C6H6O3
Molecular Weight: 126.112
Synonyms: 4H-Pyran-4-one,3-hydroxy-2-methyl-;2-Methyl-3-hydroxy-4-pyranone;2-Methyl-3-hydroxy-4-pyrone;2-Methyl-3-hydroxypyran-4-one;2-Methyl-3-hydroxypyrone;3-Hydroxy-2-methyl-1,4-pyrone;3-Hydroxy-2-methyl-4-pyranone;3-Hydroxy-2-methyl-4H-pyran-4-one;3-Hydroxy-2-methyl-g-pyrone;E 636;Larixic acid;Larixin (plant growth regulator);Larixinic acid;NSC 2829;NSC 404458;Palatone;Veltol;3-Hydroxy-2-methyl-4H-pyran-4-on;Maltol;
EINECS: 204-271-8
Density: 1.348 g/cm3
Melting Point: 160-164 °C(lit.)
Boiling Point: 284.7 °C at 760 mmHg
Flash Point: 127.32 °C
Solubility: 1.2 g/100 mL (25 °C) in water
Appearance: white crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 22-36/37/38
Safety: 26-37/39
Transport Information: N/A
PSA: 50.44000
LogP: 0.65380
Synthetic route

methyl maltol barium

A

118-71-8

Maltol

B

barium sulfate

Conditions
ConditionsYield
With sodium sulfate In water at 26℃; for 3h; Temperature; Time; Concentration;A 88.5%
B 99.8%
1198597-46-4

C15H26O3Si

118-71-8

Maltol

Conditions
ConditionsYield
With potassium acetate In water; N,N-dimethyl-formamide at 25℃; for 20h;92%
152547-41-6

3-((tert-butyldimethylsilyl)oxy)-2-methyl-4H-pyran-4-one

118-71-8

Maltol

Conditions
ConditionsYield
With lithium acetate In water; N,N-dimethyl-formamide at 25℃; for 8h; Inert atmosphere;90%

C6H8O4

118-71-8

Maltol

Conditions
ConditionsYield
With sodium hydroxide In water at -5 - 30℃; pH=2 - 3;80.5%
4208-64-4

1-(2-furyl)ethanol

118-71-8

Maltol

Conditions
ConditionsYield
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%
63493-69-6

4,6-dimethoxy-2-methyl-2H-pyran-3(6H)-one

118-71-8

Maltol

Conditions
ConditionsYield
With sulfuric acid at 25℃; for 0.333333h;74%
67171-01-1

2-(1-hydroxyethyl)-2,3,5-trimethoxy-2,5-dihydrofuran

118-71-8

Maltol

Conditions
ConditionsYield
With sulfuric acid at 25℃; for 4h;67%
In sulfuric acid67%
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
72690-06-3

trans-4-chloro-6-methoxy-2-methyl-2H-pyran-3(6H)-one

118-71-8

Maltol

Conditions
ConditionsYield
With acetic acid for 1.5h; Heating;66%
66212-70-2

4-chloro-6-methoxy-2-methyl-2H-pyran-3(6H)-one

118-71-8

Maltol

Conditions
ConditionsYield
With acetic acid65%
41728-10-3

6-methoxy-2-methyl-2H-pyran-3(6H)-one

118-71-8

Maltol

Conditions
ConditionsYield
With chlorine In acetic acid 1.) 10 deg C, 30 min; 2.) reflux 1.5 h;56%
With sodium hydroxide; chlorine In water; acetic acid56%
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
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Specification

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.