High quality Methyl cyclopentenolone CAS 80-71-7

Methyl Cyclopentenolone

(MCP), scientific name 2 hydroxy 3 armour ring pentene 2 ketones. The molecular formula C6H8O2. The structure has three tautomers, the structural formula (1) is more representative.

MCP is a natural material. In Acer, (the Department for one operation), and the Coffee in tobacco baking. L912 years.Meyerfeld first from skim dry distillation are pyroligneous acid separated and identified is 3 methyl cyclo pentane Dione [1, 2]. Occurrence of tautomerism formation of methyl Cyclopentenolone can normally.

The MCP structure with double functional group, molecular is a proton groups (OH) and a receiving proton groups (- O), and center distance of the two groups is less than 3 x 10 m, can form hydrogen bonds, causing electronic vibration. Resulting in MCP can improve the sensitivity of human taste and olfactory cells on the aroma, this is the so-called Maillard effect. Therefore, not only the MCP itself has a pleasant sweet smell, and the food and tobacco products with good increase effect of perfume.

Physical property

Appearance: white crystalline powder.

Sensory characteristics: nuts like sweet fragrance, with maple or lovage like smell. A flavor of maple sugar likelicorice in dilute solution. Sweet taste and flavor, aftertaste, enjoyable and exciting.

Melting point: 104 ~ 108 degrees

Solubility: soluble in water, ethanol, acetone, benzene alcohol, ethylene glycol, glycerol and chloroform, slightly soluble in ether. To elevate, atmospheric distillation will break down.

Chemical property

Oxidation: long term exposed in the air, it becomes yellow, was recrystallized with appropriate solvent, can remove yellow. But even if the oxidation of yellow, also do not affect its application effect.

Chemical reaction: the MCP both carbonyl and hydroxyl groups in the two groups of cyclic olefin. So it has olefin and carbonyl and hydroxyl stage multiple chemical properties, met three iron oxide formed complexes show blue purple, can participate in esterification, addition, substitution and ring opening reaction, prone to allyl alcohol tautomerism.

Preparation

Synthesis of such sweeteners, by the early 21st century, foreign nearly 20 kinds of methods. But there is worth industrialization only isoprene, oxalate and 5 methyl furfuryl alcohol method.

China generally used by glutaric acid ethyl ester two and two ethyl oxalate by Kelaixun condensation,methylation and decarboxylation reaction system:

Adipate ester in alkaline catalyst, such as the presence of alcohol, such as sodium sodium hydride, the first Lickman (Dieckman) coupling and ring of for 2 ethyl cyclopentanone and then with methyl chemical reagent Jiyou generation of alkanes, such as methyl iodide and methyl bromide or chloride methane occurred substitution reaction to generate 2 methyl 2 methyl radical ring cyclopentanone. The resultant intermediates substituted cyclopentanone after purification, and chlorine for oxychlorination reaction, generate 5, 5 - dichloro 2 methyl 2 methyl radical cyclopentanone. Finally, after acidic hydrolysis, decarboxylation, objective product MCP.

Application

Sensory properties of MCP, widely used in pastry, beverage, candy, tobacco, toothpaste and pharmaceutical industry, especially on the coffee food and tobacco aroma and flavour is particularly significant. Hygienic standard Chinese "food additives" (GB2760-2003) provisions to allow the use of edible spices. In the use of food additives, the implementation of standards for food additives "methyl Cyclopentenolone" (QB/T 2641-2004).

In post production, alone or dissolved in dilute solution dissolved into other flavors added to foods to use.

Can also be used in detergents, cosmetics and other products.

Safety

The dangerous nature: the toxicity of GRAS (FEMA).

The median lethal dose (LD50): 1400mg/kg (dove, oral).

Using a limited (mg / kg): soft drinks 11; cold 5.6; candy 18; baking food 13. Pudding 14; chewing gum 8.0 ~ 15; syrup 10. Per kilogram of food allowed to add methyl Cyclopentenolone cap to 5-18 mg.