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4-acetyl-2-isopropenyl pyridine

4-acetyl-2-isopropenyl pyridine is a pyridine-derived compound used as a flavoring agent with a herbal, green, and spearmint aroma found naturally in spearmint oil.

General Material Description

4-acetyl-2-isopropenyl pyridine, known also by its IUPAC name 1-(2-prop-1-en-2-ylpyridin-4-yl)ethanone, is a heterocyclic aromatic ketone compound belonging to the pyridine chemical class. It appears as a liquid with a characteristic herbal, green, fermented, and roasted aroma profile, demonstrating strong sensory notes reminiscent of spearmint. The molecular formula is C10H11NO, and the compound has a molecular weight of approximately 161.2 g/mol. It is found naturally in essential oils such as spearmint oil, highlighting its origin in natural plant-derived materials. This compound is linked to the PubChem database under CID 529352, facilitating detailed chemical and spectral information access. Due to its distinct odor properties, it is commonly used as a flavoring agent in various products to impart herbal and minty sensory characteristics.

Occurrence, Applicability & Potential Uses

4-acetyl-2-isopropenyl pyridine occurs naturally in spearmint oil, contributing to its complex aroma profile. Its primary use is as a flavoring agent where it provides green, herbal, and mint-like notes, especially suitable for mimicking or enhancing spearmint flavors. This makes the compound valuable in formulations of chewing gums, confectionery frostings, and soft candies among other flavor applications. The compound’s use and safety evaluations are recognized under the FEMA (US) standard, where it is assigned FEMA number 4637. FEMA’s Expert Panel has reviewed this compound, establishing usage guidelines for various food types, including maximum concentration levels in flavor formulations. It is not intended for fragrance uses, focusing strictly on flavor enhancement in food products.

Physico-Chemical Properties Summary

4-acetyl-2-isopropenyl pyridine is a liquid at room temperature with a specific gravity ranging from approximately 1.007 to 1.009 at 25 °C, indicating it is slightly denser than water. It has a refractive index between 1.517 and 1.519 measured at 20 °C. The compound exhibits a boiling point between 277 and 279 °C at standard atmospheric pressure (760 mm Hg), reflecting relative thermal stability during flavor processing. Its vapor pressure at 25 °C is low, about 0.004 mm Hg, signifying limited volatility under ambient conditions. The estimated logP value of 1.894 suggests moderate lipophilicity, influencing solubility and partition behavior in flavor matrices. Solubility in water is around 1506 mg/L at 25 °C, supporting partial aqueous dispersibility. The flash point is approximately 129 °C (264 °F), emphasizing safety considerations during handling and formulation. These physicochemical parameters affect the compound’s stability, delivery, and efficacy in flavor systems.

FAQ

What is 4-acetyl-2-isopropenyl pyridine and what are its main sensory characteristics?
4-acetyl-2-isopropenyl pyridine is a chemical compound belonging to the pyridine class, specifically characterized by an acetyl and an isopropenyl substituent. It is used primarily as a flavoring agent due to its distinctive herbal, green, and spearmint-like odor profile. This sensory signature makes it valuable for adding fresh, herbal aromas to flavor formulations, often replicating natural spearmint nuances.
Where does 4-acetyl-2-isopropenyl pyridine naturally occur and in which products is it typically used?
This compound naturally occurs in spearmint oil, contributing to the characteristic scent of this essential oil. It is employed mainly as a flavoring substance in various food products, including chewing gum, soft candies, and confectionery frostings. Its use is governed by application-specific guidelines that define suitable concentration levels to achieve desired herbal and mint flavor notes.
What regulatory standards apply to the use and safety of 4-acetyl-2-isopropenyl pyridine in flavor applications?
4-acetyl-2-isopropenyl pyridine is regulated under the FEMA (US) guidelines, with FEMA number 4637 assigned to this flavoring agent. The FEMA Expert Panel has evaluated its safety and established recommended maximum usage levels for certain food categories. No classification as hazardous under OSHA's Hazard Communication Standard is identified, and its use is specifically intended for flavoring purposes rather than fragrance. Safety data and toxicological studies can be consulted via resources such as the EPA’s ACToR system and PubChem.

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
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

General Material Information

Preferred name 4-acetyl-2-isopropenyl pyridine
Trivial Name 1-(2-prop-1-en-2-ylpyridin-4-yl)ethanone
Formula C10 H11 N O
CAS Number 142896-12-6
FEMA Number 4637
FDA UNII B6R53E7DXB
xLogP3-AA 2.00 (est)
NMR Predictor External link
JECFA Food Flavoring 2154 4-acetyl-2-isopropenylpyridine
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 142896-12-6 ; 4-ACETYL-2-ISOPROPENYLPYRIDINE
Synonyms
  • 4-acetyl-2-isopropenylpyridine
  • ethanone, 1-[2-(1-methylethenyl)-4-pyridinyl]-
  • ethanone, 1-[2-(1-methylethenyl)-4-pyridinyl]- (9CI)
  • ethanone,1-[2-(1-methylethenyl)-4-pyridinyl]-
  • ethanone,1-[2-(1-methylvinyl)-pyridin-4-yl]-
  • (2-(1-methyl ethenyl)-4-pyridinyl) ethanone
  • (2-(1-methylethenyl)-4-pyridinyl)ethanone
  • 1-[2-(1-methylethenyl)-4-pyridinyl]ethanone
  • 1-[2-( prop-1-en-2-yl)pyridin-4-yl]ethanone
  • 1-(2-prop-1-en-2-ylpyridin-4-yl)ethanone
  • pyridine, 4-acetyl-2-(1-methylethenyl)

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 161.20387268066
Specific gravity @ 25 °C
Pounds per Gallon 8.379 to 8.396
Refractive Index 1.517 to 1.519 @ 20 °C
Boiling Point 277 to 279°C @ 760 mm Hg
Vapor Pressure 0.004 mmHg @ 25 °C
Flash Point TCC Value 128.89 °C TCC
logP (o/w) 1.894 est
Solubility
water, 1506 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Herbal
herbal, green, fermented, roasted
General comment At 0.10 % in dipropylene glycol. herbal green fermented roasted

Occurrences

Potential Uses

Applications
Odor purposes Green , Herbal , Mint , Spearmint

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 4-acetyl-2-isopropenyl pyridine 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: 24
Click here to view publication 24
average usual ppmaverage maximum ppm
baked goods: --
beverages(nonalcoholic): --
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: 0.100000.50000
condiments / relishes: --
confectionery froastings: 0.050000.30000
egg products: --
fats / oils: --
fish products: --
frozen dairy: --
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: 0.050000.30000
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: 0.100000.50000
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :529352
National Institute of Allergy and Infectious Diseases:Data
1-(2-prop-1-en-2-ylpyridin-4-yl)ethanone
Chemidplus:0142896126