80-71-7 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 80-71-7 differently. You can refer to the following data:
1. 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.
2. 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
Different sources of media describe the Uses of 80-71-7 differently. You can refer to the following data:
1. 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.
2. 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.
Check Digit Verification of cas no
The CAS Registry Mumber 80-71-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 0 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 80-71:
(4*8)+(3*0)+(2*7)+(1*1)=47
47 % 10 = 7
So 80-71-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H8O2/c1-4-2-3-5(7)6(4)8/h4H,2-3H2,1H3/t4-/m1/s1
80-71-7Relevant articles and documents
Shiozaki,Hiraoka
, p. 4655 (1972)
Prostaglandins VI base-catalysed autoxidation of α-hydroxycyclopentanonesand the synthesis of 9,10-diketoprostanoic acids
Caton,Darnbrough,Parker
, p. 1685 - 1686 (1980)
-
Green synthesis method of methyl cyclopentenolone
-
Paragraph 0055-0066, (2020/12/05)
The invention relates to a green synthesis method of methyl cyclopentenolone, and belongs to the field of organic synthesis. The method comprises the following synthesis steps: A, carrying out Mannichreaction on 2-methyl furan serving as a raw material and piperidine hydrochloride to generate an aminated intermediate; B, adding a catalytic amount of sulfuric acid into the aminated intermediate for reflux reaction to obtain a hydrolysate; and C, adding the hydrolysate into methylbenzene, neutralizing to be neutral by using sodium hydroxide, adding piperidine and pyridine, refluxing and separating water until no water is separated out, and rectifying to obtain a cyclized product; and D, putting the cyclized product into an acetic acid-hydrochloric acid solution for reflux reaction, cooling,removing piperidine hydrochloride, removing acetic acid from the filtrate, adding water, and crystallizing to obtain methyl cyclopentenolone. According to the method, the generation of wastewater andwaste salt is greatly reduced, the generated piperidine hydrochloride can be recycled and reused, and the method is a green synthetic method for synthesizing methyl cyclopentenolone.
Cyclopentanone Derivatives from 5-Hydroxymethylfurfural via 1-Hydroxyhexane-2,5-dione as Intermediate
Wozniak, Bartosz,Spannenberg, Anke,Li, Yuehui,Hinze, Sandra,de Vries, Johannes G.
, p. 356 - 359 (2018/01/03)
An efficient strategy for the conversion of biomass derived 5-hydroxymethylfurfural (HMF) into 2-hydroxy-3-methylcyclopent-2-enone (MCP) by an intramolecular aldol condensation of 1-hydroxyhexane-2,5-dione (HHD) has been developed. Further transformations of MCP towards the diol, enol acetate, levulinic acid and N-heterocyclic compounds are also reported.
