| Identification | More | [Name]
Methyl cyclopentenolone | [CAS]
80-71-7 | [Synonyms]
2-HYDROXY-3-METHYL-2-CYCLOPENTEN-1-ONE
2-HYDROXY-3-METHYL-2-CYCLOPENTENE-1-ONE
2-HYDROXY-3-METHYL-2-CYCLOPENTENONE
2-HYDROXY-3-METHYLCYCLOPENT-2-ENONE
3-METHYL-1,2-CYCLOPENTANEDIONE
3-METHYL-2-CYCLOPENTENON-2-OL
3-METHYL-2-HYDROXY-2-CYCLOPENTENONE
CYCLOTENE
FEMA 2700
METHYL CYCLOPENTENOLONE
RARECHEM AQ C5 0001
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
3-Methyl-1,2-cyclopentanedione (cyclotene)
3-Methyl-2-cyclopenten-2-ol-1-one
3-Methyl-2-cyclopentene-2-ol-1-one
3-Methyl-2-cyclopentene-2-olone | [EINECS(EC#)]
201-303-2 | [Molecular Formula]
C6H8O2 | [MDL Number]
MFCD00013747 | [Molecular Weight]
112.13 | [MOL File]
80-71-7.mol |
| Chemical Properties | Back Directory | [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 | [refractive index ]
1.4532 (estimate) | [Fp ]
100°C | [storage temp. ]
Store at +2°C to +8°C. | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
neat | [pka]
9.21±0.20(Predicted) | [color ]
White crystalline powder or fine crystals | [Odor]
at 1.00 % in dipropylene glycol. caramel maple syrup | [Odor Type]
caramellic | [Detection Methods]
HPLC.NMR | [JECFA Number]
418 | [LogP]
0.4 at 25℃ | [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. | [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]
80-71-7(EPA Substance) |
| Hazard Information | Back Directory | [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). | [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. |
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