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Methyl cyclopentenolone

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Methyl cyclopentenolone

EINECS 201-303-2
CAS No. 80-71-7 Density 1.225 g/cm3
PSA 37.30000 LogP 1.18130
Solubility easily soluble in boiling water Melting Point 104-108 °C
Formula C6H8O2 Boiling Point 245.2 °C at 760 mmHg
Molecular Weight 112.128 Flash Point 100.7 °C
Transport Information N/A Appearance White crystalline powder
Safety 26-36/37-24/25-22 Risk Codes 36/37/38-43
Molecular Structure Molecular Structure of 80-71-7 (Methyl cyclopentenolone) Hazard Symbols Xi
Synonyms

2-Hydroxy-1-methylcyclopenten-3-one;2-Hydroxy-3-methyl-2-cyclopenten-1-one;2-Hydroxy-3-methyl-2-cyclopentene-1-one;2-Hydroxy-3-methyl-2-cyclopentenone;3-Methyl-2-hydroxy-2-cyclopentenone;3-Methylcyclopent-2-en-2-ol-1-one;Corylon;Corylone;Cycloten;Cyclotene;Cyclotene (odorant);Maple lactone;NSC133445;NSC 84226;

Article Data 51

Methyl cyclopentenolone Consensus Reports

Reported in EPA TSCA Inventory.

Methyl cyclopentenolone Specification

The IUPAC name of 2-Hydroxy-3-methyl-2-cyclopenten-1-one is 2-hydroxy-3-methylcyclopent-2-en-1-one. With the CAS registry number 80-71-7, it is also named as Cyclotene. The product's category is Clcohol Flavor. It is white crystalline powder which is easily soluble in boiling water, soluble in ethanol, acetone and propylene glycol, and slightly soluble in most non-volatile oil. Besides, this chemical can be obtained by methyl furan and dimethylamine. When heated to decomposition it emits acrid smoke and fumes.

The other characteristics of 2-Hydroxy-3-methyl-2-cyclopenten-1-one can be summarized as: (1)ACD/LogP: 0.30; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.3; (4)ACD/LogD (pH 7.4): 0.29; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 34.75; (8)ACD/KOC (pH 7.4): 34.22; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.548; (13)Molar Refractivity: 29.08 cm3; (14)Molar Volume: 91.4 cm3; (15)Polarizability: 11.52×10-24 cm3; (16)Surface Tension: 49.8 dyne/cm; (17)Enthalpy of Vaporization: 56.04 kJ/mol; (18)Vapour Pressure: 0.00484 mmHg at 25°C; (19)Tautomer Count: 16; (20)Exact Mass: 112.05243; (21)MonoIsotopic Mass: 112.05243; (22)Topological Polar Surface Area: 37.3; (23)Heavy Atom Count: 8; (24)Complexity: 156.

Uses of 2-Hydroxy-3-methyl-2-cyclopenten-1-one: It is used as synergist of flavor and sweetness. It is mainly used for the preparation of essence such as maple, fumigation, cream hard candy and apricot. In addition, this chemical can react with chloro-trimethyl-silane to get 1-methyl-2,3-bis(trimethylsilyloxy)-1,3-cyclopentadiene. This reaction needs reagent triethylamine, LiBr and solvent tetrahydrofuran. The yield is 93%. 

People can use the following data to convert to the molecule structure.
1. SMILES:O=C1C(/O)=C(/C)CC1
2. InChI:InChI=1/C6H8O2/c1-4-2-3-5(7)6(4)8/h8H,2-3H2,1H3 
3. InChIKey:CFAKWWQIUFSQFU-UHFFFAOYAU

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 1400mg/kg (1400mg/kg)   Food and Cosmetics Toxicology. Vol. 14, Pg. 809, 1976.
mouse LDLo intraperitoneal 500mg/kg (500mg/kg)   Food and Cosmetics Toxicology. Vol. 14, Pg. 809, 1976.
rat LDLo intraperitoneal 500mg/kg (500mg/kg)   Food and Cosmetics Toxicology. Vol. 14, Pg. 809, 1976.

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