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2-acetyl-4-isopropyl pyridine

2-acetyl-4-isopropyl pyridine is a flavoring agent with a green, grassy odor, found naturally in peppermint and spearmint oils and used in flavor formulations.

General Material Description

2-acetyl-4-isopropyl pyridine is an organic compound classified as a pyridine derivative with the molecular formula C10H13NO. It appears as a colorless to pale liquid and is distinguished by a green, grassy odor with herbal and violet undertones when diluted in solvents like dipropylene glycol. This compound is also known by synonyms such as 1-(4-propan-2-ylpyridin-2-yl)ethanone and contains a pyridine ring substituted with an acetyl group and an isopropyl group. Its chemical structure and properties are documented in controlled-vocabulary databases such as PubChem. The compound naturally occurs in essential oils like peppermint and spearmint and is commonly synthesized for use as a flavoring agent in food products.

Occurrence, Applicability & Potential Uses

2-acetyl-4-isopropyl pyridine is found biologically in Mentha gentilis f. cardiaca, peppermint oil, and spearmint oil, contributing characteristic green and herbal notes to these plants. It is applied primarily as a flavoring agent in food and beverage formulations, imparting a distinctive green odor profile. The compound's use conforms to the standards set by FEMA (US), with a FEMA number of 4638. This ensures its evaluation and acceptance for flavor use under regulated conditions. Typical application areas include chewing gum, confectionery frostings, hard candy, and soft candy, where it provides nuanced green and grassy flavor notes without use in fragrance products.

Physico-Chemical Properties Summary

This compound exhibits moderate volatility, with a boiling point ranging between 245 and 247 °C at standard atmospheric pressure. Its specific gravity at 25 °C lies between 0.992 and 0.994, indicating a density near that of water but slightly less. The refractive index at 20 °C ranges from 1.502 to 1.505, consistent with typical organic aromatic compounds. Its logP of approximately 2.45 suggests moderate lipophilicity, affecting its solubility and partitioning behavior. Solubility properties indicate limited aqueous solubility (approximately 1455 mg/L at 25 °C, estimated) but good solubility in alcohol solvents. The vapor pressure of 0.028 mmHg at 25 °C reflects low volatility under ambient conditions, traits important for flavor formulation stability and volatility control.

FAQ

What is 2-acetyl-4-isopropyl pyridine, and what are its characteristics?
2-acetyl-4-isopropyl pyridine is a pyridine derivative used primarily as a flavoring agent. It has a molecular weight of approximately 163.22 and features a green, grassy, and herbal odor profile. This compound naturally occurs in peppermint and spearmint oils. Chemically, it contains an acetyl group at the 2-position and an isopropyl group at the 4-position of the pyridine ring. Its sensory profile makes it valuable in imparting fresh green notes to food products.
Where does 2-acetyl-4-isopropyl pyridine occur naturally, and how is it applied industrially?
This compound is found naturally in essential oils such as peppermint oil, spearmint oil, and Mentha gentilis f. cardiaca. Industrially, it is utilized as a flavoring agent in various food categories, including chewing gum, confectionery frostings, and soft and hard candies. Its inclusion in formulations enhances green, leafy, and herbal aroma qualities. Usage guidelines are defined by regulatory authorities to ensure safe concentrations in food products.
What regulations and safety considerations apply to 2-acetyl-4-isopropyl pyridine in flavor usage?
2-acetyl-4-isopropyl pyridine holds FEMA number 4638 and is recognized under FEMA (US) guidelines for flavor use. The compound is recommended for use only as a flavoring agent and not for fragrance applications. Safety assessments indicate no significant hazard classifications based on OSHA criteria, and precautionary statements are not mandated. Usage levels vary across food categories, with typical maximum concentrations of 0.5 parts per million in some confectionery items. Regulatory compliance ensures controlled and safe application in food products.

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 2-acetyl-4-isopropyl pyridine
Trivial Name 1-(4-propan-2-ylpyridin-2-yl)ethanone
Formula C10 H13 N O
CAS Number 142896-09-1
FEMA Number 4638
FDA UNII JRF96H7XWL
xLogP3-AA 2.00 (est)
NMR Predictor External link
JECFA Food Flavoring 2155 2-acetyl-4-isopropylpyridine
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 142896-09-1 ; 2-ACETYL-4-ISOPROPYLPYRIDINE
Synonyms
  • 2-acetyl-4-isopropylpyridine
  • ethanone, 1-[4-(1-methylethyl)-2-pyridinyl]-
  • ethanone, 1-[4-(1-methylethyl)-2-pyridinyl]- (9CI)
  • ethanone,1-[4-(1-methylethyl)-2-pyridinyl]-
  • ethanone,1-[4-(isopropyl)-pyridin-2-yl]-
  • (4-(1-methyl ethyl)-2-pyridinyl) ethanone
  • (4-(1-methylethyl)-2-pyridinyl) ethanone
  • (4-(1-methylethyl)-2-pyridinyl)ethanone
  • 1-[4-(1-methylethyl)-2-pyridinyl]ethanone
  • 1-(4-propan-2-ylpyridin-2-yl)ethanone
  • 1-(4-iso propylpyridin-2-yl)ethanone
  • pyridine, 2-acetyl-4-(1-methylethyl)

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 163.21980285645
Specific gravity @ 25 °C
Pounds per Gallon 8.254 to 8.271
Refractive Index 1.502 to 1.505 @ 20 °C
Boiling Point 245 to 247°C @ 760 mm Hg
Vapor Pressure 0.028 mmHg @ 25 °C
Flash Point TCC Value 108.8 °C TCC
logP (o/w) 2.45 est
Solubility
alcohol Yes
water, 1455 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Green
grassy, green, leafy, herbal, violet
General comment At 0.10 % in dipropylene glycol. grassy green leafy herbal violet

Occurrences

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 2-acetyl-4-isopropyl 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 :529345
National Institute of Allergy and Infectious Diseases:Data
1-(4-propan-2-ylpyridin-2-yl)ethanone
Chemidplus:0142896091