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80-71-7

Basic Information
CAS No.: 80-71-7
Name: 2-Cyclopenten-1-one,2-hydroxy-3-methyl-
Molecular Structure:
Molecular Structure of 80-71-7 (2-Cyclopenten-1-one,2-hydroxy-3-methyl-)
Formula: C6H8O2
Molecular Weight: 112.14
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;
EINECS: 201-303-2
Density: 1.225 g/cm3
Melting Point: 104-108 °C
Boiling Point: 245.2 °C at 760 mmHg
Flash Point: 100.7 °C
Solubility: easily soluble in boiling water
Appearance: White crystalline powder
Hazard Symbols: Xi
Risk Codes: 36/37/38-43
Safety: 26-36/37-24/25-22
Transport Information:
PSA: 37.30000
LogP: 1.18130
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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.