Methyl cyclopentenolone Property

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)

color 

White crystalline powder or fine crystals

Odor

at 1.00 % in dipropylene glycol. caramel maple syrup

Odor Type

caramellic

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)

Safety

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H317May cause an allergic skin reaction

H318Causes serious eye damage

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Methyl cyclopentenolone Chemical Properties,Usage,Production

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)

Application

Methyl cyclopentenolone is used sparingly in perfume compositions often in combination with Coumarin or Coumarin derivatives. It is an excellent fortifier for such materials in Lavender fragrances, New Mown Hay, "tabac" type fragrances, spicy bases, etc. It falls naturally into Celery seed oil, Lovage, Fenugreek, Tonka, Liatris, Flouve, etc. It is, however, in flavor compositions that Methyl cyclopentenolone has found its truly extensive application.

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.