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2-hexyl pyridine

2-hexyl pyridine is a pyridine derivative with green fatty and nutty flavor notes, used as a flavoring agent primarily in meat and lamb products.
Chemical Structure

General Material Description

2-hexyl pyridine is an organic compound classified as a pyridine derivative, with the molecular formula C11H17N. It appears as a chemical substance identified primarily by its position of the hexyl substituent on the pyridine ring at the 2-position. This compound exhibits distinctive green, fatty, and nutty sensory notes, characteristic of its use in flavor formulation. Known synonyms include 2-hexylpyridine, 2-(N-hexyl)pyridine, and pyridine, 2-hexyl-. The compound is registered under several chemical databases such as PubChem (CID 70797). It is predominantly derived synthetically but also occurs naturally in certain food sources like lamb fat and cooked mutton. 2-hexyl pyridine is utilized mainly in flavoring applications to impart green and fatty notes, especially in meat and vegetable flavor profiles.

Occurrence, Applicability & Potential Uses

2-hexyl pyridine naturally occurs in lamb fat and heated mutton, contributing green, fatty, and nutty flavor impressions characteristic of these foodstuffs. Its role as a flavoring agent is recognized in various meat-related and vegetable flavor formulations. Usage concentrations typically range up to 1 ppm in flavor blends. Regulatory evaluation by FEMA (US) includes its designation under FEMA number 4948, where it is considered safe for use within specified levels. The compound enhances the sensory profile of lamb, meat, and vegetable flavors by adding green and fatty notes, which makes it valuable in flavor development and reformulation. Its physicochemical properties support incorporation in various food matrices where such sensory qualities are desired.

Physico-Chemical Properties Summary

2-hexyl pyridine has a molecular weight of approximately 163.26 g/mol and a molecular formula C11H17N. It exhibits a boiling point range near 225 to 227 °C at atmospheric pressure. The compound’s refractive index lies between 1.48 and 1.49 at 20 °C, while its specific gravity ranges from 0.892 to 0.902 at 25 °C. The estimated partition coefficient logP is 3.766, indicating moderate hydrophobicity. Vapor pressure is low at 0.112 mmHg at 25 °C, suggesting limited volatility under ambient conditions. Solubility is reported as soluble in alcohol and partially in water (~739 mg/L at 25 °C estimated), but it is not fully miscible with water. These physical properties facilitate formulation in flavor matrices, typically at low concentrations where its green and fatty aroma notes are perceptible. The flash point is 164 °C, enhancing considerations for safe handling and processing.

FAQ

What is 2-hexyl pyridine and what are its main characteristics?
2-hexyl pyridine is an organic compound from the pyridine family, marked by a hexyl group at the 2-position on the pyridine ring. It is characterized by a green, fatty, and nutty odor profile and mainly serves as a flavoring agent in various food products. The compound is naturally present in lamb fat and heated mutton and is synthesized for use in flavor applications most often related to meat and vegetable flavors.
How is 2-hexyl pyridine used and where does it naturally occur?
This compound is primarily employed as a flavoring ingredient to impart green fatty notes, typically at levels up to 1 ppm in formulations. It naturally occurs in lamb fat and in mutton when heated, contributing to the characteristic aroma of these meats. Its physicochemical properties allow it to be incorporated effectively into various flavor systems including those for meats, vegetables, and nuts.
What regulations govern the use and safety of 2-hexyl pyridine in flavorings?
2-hexyl pyridine is evaluated under flavoring regulatory frameworks such as FEMA (US), where it is registered under FEMA number 4948 and considered acceptable within certain use levels. Safety assessments include references from agencies like the European Food Safety Authority (EFSA) and its use complies with regulations including Commission Regulation (EC) No. 1565/2000 (EU). Recommended usage levels are established to ensure consumer safety, and it is not intended for fragrance use. Toxicological data indicate no significant hazard classification under OSHA standards.

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
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2933.39.9050
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

General Material Information

Preferred name 2-hexyl pyridine
Trivial Name 2-Hexylpyridine
Short Description pyridine, 2-hexyl-
Formula C11 H17 N
CAS Number 1129-69-7
FEMA Number 4948
Flavis Number 14.117
ECHA Number 214-454-4
FDA UNII Search
Nikkaji Number J45.677B
Beilstein Number 0114710
NMR Predictor External link
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
Synonyms
  • 2-hexylpyridine
  • 2-(N-hexyl) pyridine
  • 2-(N-hexyl)pyridine
  • 2-(n-Hexyl)pyridine
  • 2-Hexylpyridine
  • 2-N-hexylpyridine
  • pyridine, 2-hexyl-

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 163.26348876953
Specific gravity @ 25 °C
Pounds per Gallon 7.422 to 7.506
Refractive Index 1.48 to 1.49 @ 20 °C
Boiling Point 225 to 227°C @ 760 mm Hg
Vapor Pressure 0.112 mmHg @ 25 °C
Flash Point TCC Value 73.33 °C TCC
logP (o/w) 3.766 est
Solubility
alcohol Yes
water, 739.4 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Green
green, fatty, mutton
General comment At 0.10 % in propylene glycol. green fatty mutton
Flavor Type: Green
green, vegetable, nutty
General comment Green vegetable nutty
Used in vegetable, meat and nut flavours, up to 1ppm. Green

Occurrences

Potential Uses

Applications
Flavoring purposes Lamb , Lamb , Meat

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:
oral-rat LDLo > 500 mg/kg
National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 23, 1953.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavoring agents
Recommendation for 2-hexyl pyridine usage levels up to:
not for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.012 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 400 (μg/person/day)
Threshold of Concern:540 (μg/person/day)
Structure Class: II
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: 30
Click here to view publication 30
average usual ppmaverage maximum ppm
baked goods: 1.000005.00000
beverages(nonalcoholic): 1.000005.00000
beverages(alcoholic): 1.000005.00000
breakfast cereal: --
cheese: 1.000005.00000
chewing gum: --
condiments / relishes: 1.000005.00000
confectionery froastings: --
egg products: 1.000005.00000
fats / oils: 1.000005.00000
fish products: 1.000005.00000
frozen dairy: --
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: 1.000005.00000
hard candy: --
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: 1.000005.00000
milk products: --
nut products: --
other grains: --
poultry: 1.000005.00000
processed fruits: --
processed vegetables: 1.000005.00000
reconstituted vegetables: 1.000005.00000
seasonings / flavors: 1.000005.00000
snack foods: 1.000005.00000
soft candy: --
soups: 1.000005.00000
sugar substitutes: --
sweet sauces: --
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 0.400002.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 0.100000.50000
Edible ices, including sherbet and sorbet (03.0): 0.400002.00000
Processed fruit (04.1): 0.400002.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 1.000005.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 0.200001.00000
Bakery wares (07.0): 2.0000010.00000
Meat and meat products, including poultry and game (08.0): 0.200001.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 0.200001.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 0.100000.50000
Foodstuffs intended for particular nutritional uses (13.0): 0.200001.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 0.200001.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): --
Ready-to-eat savouries (15.0): 1.000005.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 0.200001.00000

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 24 (FGE.24): Pyridine, pyrrole, indole and quinoline derivatives from chemical group 28 (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
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Pyridine, pyrrole, indole and quinoline derivatives from chemical group 28 Flavouring Group Evaluation 24, Revision 1 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
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Flavouring Group Evaluation 77 (FGE77) [1] - Consideration of Pyridine, Pyrrole and Quinoline Derivatives evaluated by JECFA (63rd meeting) structurally related to Pyridine, Pyrrole, Indole and Quinoline Derivatives evaluated by EFSA in FGE.24Rev1 (2008)
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Scientific opinion on Flavouring Group Evaluation 24, Revision 2 (FGE.24Rev2): Pyridine, pyrrole, indole and quinoline derivatives from chemical group 28
View page or View pdf

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EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :70797
National Institute of Allergy and Infectious Diseases:Data
2-hexylpyridine
Chemidplus:0001129697