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Methyl cyclopentenolone

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Methyl cyclopentenolone Basic information

Product Name:
Methyl cyclopentenolone
Synonyms:
  • 2-HYDROXY-3-METHYLCYCLOPENT-2-ENONE
  • 2-HYDROXY-3-METHYL-2-CYCLOPENTENE-1-ONE
  • 2-HYDROXY-3-METHYL-2-CYCLOPENTENONE
  • 2-Hydroxy-1-methylcyclopenten-3-one
  • 2-hydroxy-3-methyl-2-cyclopenten-1-on
  • 2-hydroxy-3-methyl-2-cyclopenten1-one (cycloten)
  • 2-Hydroxy-3-methyl-2-cyclopenten-1-one (cyclotene)
  • 2-Hydroxy-3-methylcyclopent-2-en-1-one
CAS:
80-71-7
MF:
C6H8O2
MW:
112.13
EINECS:
201-303-2
Product Categories:
  • insect pheromone
  • alcohol Flavor
Mol File:
80-71-7.mol
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Methyl cyclopentenolone Chemical Properties

Melting point:
104-108°C
Boiling point:
170.05°C (rough estimate)
Density 
1.0795 (rough estimate)
vapor pressure 
2.1hPa at 20℃
FEMA 
2700 | METHYLCYCLOPENTENOLONE
refractive index 
1.4532 (estimate)
Flash point:
100°C
storage temp. 
Store at +2°C to +8°C.
solubility 
Chloroform (Slightly), Methanol (Slightly)
pka
9.21±0.20(Predicted)
form 
neat
color 
White crystalline powder or fine crystals
JECFA Number
418
LogP
0.4 at 25℃
CAS DataBase Reference
80-71-7(CAS DataBase Reference)
NIST Chemistry Reference
2-Cyclopenten-1-one, 2-hydroxy-3-methyl-(80-71-7)
EPA Substance Registry System
Maple lactone (80-71-7)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38-43
Safety Statements 
26-36/37-24/25-22
WGK Germany 
3
RTECS 
GY7298000
HS Code 
29144090

MSDS

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Methyl cyclopentenolone Usage And Synthesis

Chemical Properties

Methyl cyclopentenolone occurs in beechwood tar and has a caramel-like (burnt sugar) odor. It has been identified as a flavor component in food. Crystals of the compound usually contain 1 mol of water. Synthetic routes of production are of limited importance in comparison with isolation from beechwood tar. Homologs of cyclotene such as 3-ethyl-2-hydroxy-2-cyclopenten-1-one, C7H10O2, Mr 126.16, 2-hydroxy-3,4-dimethyl-2-cyclopenten-1-one, C7H10O2, Mr 126.16, and 2-hydroxy-3,5-dimethyl-2-cyclopenten-1-one, C7H10O2, Mr 126.16, are also used as flavor ingredients and have similar caramel-like properties.
Cyclotene and its homologs are frequently used in flavor compositions for its caramel note, for example, in beverages and in confectionery.

Chemical Properties

Off-white solid

Occurrence

Reported to be found during the dry distillation of wood and in the corresponding tar oil. It has also been identified in fenugreek (FenaroWs Handbook of Flavor Ingredients, 1975).

Uses

Methyl Cyclopentenolone is a flavoring agent that is a white crys- talline powder. it has a nutty odor suggesting a maple-licorice aroma when diluted. it is soluble in alcohol and propylene glycol, slightly soluble in most fixed oils, and sparingly soluble in water. it is obtained by synthesis. it is also termed 3-methyl-cyclopentane-1,2-dione.

Uses

Methyl cyclopentenolone may be used as an analytical reference standard for the quantification of the analyte in commercial products using different chromatography techniques.

Preparation

By ketonic hydrolysis of the corresponding dicarboxylic ester (Arctander, 1969)

Toxicity evaluation

The acute oral LD50 value in guinea-pigs was reported as 1.4 g/kg (Dow Chemical Company, 1953) and that in rats as > 1.85 g/kg, while the acute dermal LD50 value in guinea-pigs exceeded 2 g/kg (Moreno, 1976). Methylcyclopentenolone was lethal to mice and rats at ip doses of 0.5-1 g/kg (Shugaev, 1959), and at a concentration of 7 χ 10-4 m was toxic to cultured human leucocytes (Withers, 1966).

General Description

Methyl cyclopentenolone is one of the flavor compounds of maple syrup, coffee oil and wood smoke. It is reported to be one the key aroma compounds in Wasanbon sugar, contributing to the maple-like flavor. Methyl cyclopentenolone is also one of the major volatile compound formed during the thermal degradation of glucose.

Methyl cyclopentenolone Preparation Products And Raw materials

Raw materials

Methyl cyclopentenoloneSupplier

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