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menthyl pyrrolidone carboxylate

Menthyl pyrrolidone carboxylate is a synthetic cooling flavoring agent with a mentholic minty profile used primarily in food and flavor applications.

General Material Description

Menthyl pyrrolidone carboxylate is a synthetic organic compound characterized by the molecular formula C15H25NO3. It appears as a solid with a melting point ranging approximately from 68 to 72°C. Known by several synonyms including (-)-menthyl (+)-2-pyrrolidone-5-carboxylate and the trivial name (5-methyl-2-propan-2-ylcyclohexyl) 5-oxopyrrolidine-2-carboxylate, this compound imparts a cooling, mentholic minty sensation. It is closely associated with the controlled vocabulary entry available on PubChem for further structural and chemical data. Derived through synthetic chemistry methods, menthyl pyrrolidone carboxylate is utilized primarily for its distinctive organoleptic properties in flavor formulations.

Occurrence, Applicability & Potential Uses

While not naturally widespread in biological sources, menthyl pyrrolidone carboxylate functions predominantly as a flavoring compound in the food industry. It delivers cooling and minty sensations similar to menthol but with distinct sensory profiles. The compound finds application in various flavored products, notably in chewing gum, where FEMA (US) regulation supports usage up to 3000 ppm, and in hard candies with authorized levels up to 500 ppm, reflecting its approval and safety assessment by the Flavor and Extract Manufacturers Association. Its structural characteristics and sensory effects make it suitable for inclusion in flavoring blends to enhance freshness and cooling attributes.

Physico-Chemical Properties Summary

Menthyl pyrrolidone carboxylate exhibits a moderate molecular weight of approximately 267.37 g/mol and a melting point between 68 and 72°C at atmospheric pressure. It has a high boiling point around 409 to 410°C under standard pressure, indicating thermal stability suitable for processing conditions typical in flavor manufacturing. The estimated log P of about 3.2 suggests moderate lipophilicity, supporting solubility in alcohols and limited water solubility near 14 mg/L at 25°C. These properties influence its solubility profile and interaction within flavor formulations, favoring dissolution in organic solvents over aqueous media. The flash point is high, around 394°F (201°C), reducing flammability risks under normal handling conditions.

FAQ

What is menthyl pyrrolidone carboxylate and what is its primary application?
Menthyl pyrrolidone carboxylate is a synthetic chemical compound used primarily as a flavoring agent. It provides a cooling and mentholic minty taste that enhances sensory profiles in food products. This compound is valued especially in chewing gums and candies for its distinctive cooling effect that mimics menthol but with subtle differences in olfactory perception.
How is menthyl pyrrolidone carboxylate used in food products and what sensory properties does it impart?
This compound is incorporated into flavor formulations for products such as chewing gum and hard candies. It contributes a pronounced cooling sensation along with fresh minty notes that intensify flavor freshness and perception. Its moderate solubility in alcohols facilitates its blending into flavor concentrates while partial water solubility permits controlled release in aqueous food matrices. Documented usage levels by FEMA (US) confirm its role as a recognized flavor constituent within regulated limits.
What are the regulatory considerations and sourcing for menthyl pyrrolidone carboxylate?
Menthyl pyrrolidone carboxylate is listed under FEMA number 4155 and has been evaluated by the FEMA Expert Panel (US), which supports its designation as Generally Recognized As Safe (GRAS) for flavor use within specified limits. It is not intended for fragrance applications. The compound is synthesized chemically and available from flavor ingredient suppliers, including special trade names like questice from Givaudan. Regulatory documents and chemical safety databases provide detailed chemical and toxicological profiles for compliance purposes.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
KEGG (GenomeNet):C03962
HMDB (The Human Metabolome Database):HMDB32368
FooDB:FDB009781
ChemSpider:View

General Material Information

Preferred name menthyl pyrrolidone carboxylate
Trivial Name (5-methyl-2-propan-2-ylcyclohexyl) 5-oxopyrrolidine-2-carboxylate
Formula C15 H25 N O3
CAS Number 68127-22-0
CAS Number 64519-44-4
Deleted CAS Number 52528-10-6
FEMA Number 4155
ECHA Number 268-568-4
FDA UNII Y27B4585KO
Nikkaji Number J307.247I
xLogP3-AA 3.00 (est)
NMR Predictor External link
JECFA Food Flavoring 1858 menthyl pyrrolidone carboxylate
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 52528-10-6 ; MENTHYL PYRROLIDONECARBOXYLATE
Synonyms
  • (-)- menthyl (+)-2-pyrrolidone-5-carboxylate
  • menthyl PCA
  • (5-methyl-2-propan-2-ylcyclohexyl) 5-oxopyrrolidine-2-carboxylate
  • [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (2S)-5-oxopyrrolidine-2-carboxylate
  • (1R-(1alpha,2beta,5alpha))-2-iso propyl-5-methyl cyclohexyl 5-oxo-dextro-prolinate
  • (1R-(1alpha,2beta,5alpha))-2-iso propyl-5-methylcyclohexyl 5-oxo-D-prolinate
  • questice (Givaudan)

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 267.36883544922
Melting Point 68 to 72°C @ 760 mm Hg
Boiling Point 409 to 410°C @ 760 mm Hg
Flash Point TCC Value 201.11 °C TCC
logP (o/w) 3.195 est
Solubility
alcohol Yes
water, slightly Yes
water, 14.07 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Flavor Type: Cooling
cooling, mentholic, minty
General comment Cooling mentholic minty

Safety Information

Safety information

Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavoring agents
Recommendation for menthyl pyrrolidone carboxylate usage levels up to:
not for fragrance use.
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 22
Click here to view publication 22
average usual ppmaverage maximum ppm
baked goods: --
beverages(nonalcoholic): --
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: 3000.000003000.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: --
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: 500.00000500.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):68127-22-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :109140
National Institute of Allergy and Infectious Diseases:Data
(5-methyl-2-propan-2-ylcyclohexyl) 5-oxopyrrolidine-2-carboxylate
Chemidplus:0068127220
[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (2S)-5-oxopyrrolidine-2-carboxylate
Chemidplus:0064519444