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1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one

1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one is a synthetic flavoring compound known for its sweet savory odor and salty umami flavor notes, used mainly as a food flavoring agent.

General Material Description

1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one is a synthetic organic compound recognized for its distinctive flavor and aroma profile. It appears as a compound containing carbon (C15), hydrogen (H15), nitrogen (N), and oxygen (O3) atoms, with a molecular weight of approximately 257.29 g/mol. The structure combines a hydroxy-methoxy-substituted phenyl group linked to a 2-pyridinyl moiety via a propanone bridge. This compound exhibits a sweet, savory odor and imparts salty and umami taste notes, which makes it valuable in flavoring applications. Synonyms include 1-(2-hydroxy-4-methoxyphenyl)-3-(2-pyridyl)propan-1-one and 1-propanone, 1-(2-hydroxy-4-methoxyphenyl)-3-(2-pyridinyl)-. PubChem provides comprehensive chemical data under CID 49869549. The compound is synthetically derived and utilized primarily in the food industry as a flavor ingredient, rather than sourced naturally.

Occurrence, Applicability & Potential Uses

This compound does not naturally occur but is synthetically produced for use as a flavoring agent in food products. It is particularly effective in enhancing savory, salty, and umami flavor profiles, making it suitable for applications in baked goods, cheeses, meat products, gravies, seasonings, and snack foods. The United States FEMA Expert Panel classifies it under FEMA GRAS standards, supporting its use within regulated levels in food formulations (FEMA (US)). Typical usage concentrations vary by product type, generally ranging from low single parts per million up to 50 ppm in seasonings and flavorings. Due to its unique sensory characteristics, it is incorporated to augment palatability and flavor complexity without contributing fragrance attributes.

Physico-Chemical Properties Summary

1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one exhibits a melting point between 65 and 66°C at standard pressure and a boiling point range of 456 to 457°C at 760 mm Hg, indicating notable thermal stability. Its estimated logP value of approximately 2.8 suggests moderate lipophilicity, enabling solubility in organic solvents such as alcohols, while showing limited water solubility around 3969 mg/L at 25°C. The compound's high flash point (~446°F) indicates relatively low volatility under normal handling conditions. These physicochemical properties are critical for formulation scientists aiming to balance flavor release and stability in complex food matrices.

FAQ

What is 1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one?
1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one is a synthetic organic flavor compound characterized by a sweet savory odor and salty, umami taste notes. It is chemically composed of a substituted phenyl group connected to a pyridine ring via a propanone linker. This compound functions predominantly as a flavoring agent in various food products, enhancing savory and salty flavor profiles.
How is this compound used and where does it typically occur?
This compound is not found in nature but is manufactured synthetically for use in the food industry to impart savory and umami flavors. It is applied in baked goods, cheeses, meat products, gravies, seasonings, and snack foods, among others. Its incorporation is regulated by organizations such as the FEMA Expert Panel in the United States, which provides guidelines for safe usage levels in different food categories.
What regulations and safety information apply to 1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one?
The flavor compound is recognized as Generally Recognized as Safe (GRAS) by the FEMA Expert Panel (US) for use as a flavoring agent within prescribed concentration limits. It is not intended for fragrance applications. Safety data indicate no classified hazards under OSHA's Hazard Communication Standard, with limited toxicity data available. Regulatory compliance involves adhering to maximum usage levels in food products, and references to authoritative sources such as JECFA and FDA databases provide further guidance.

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

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Literature & References

1-(2-hydroxy-4-methoxyphenyl)-3-(2-pyridyl)propan-1-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):49869549
Pubchem (sid):342527123
Publications by WIPO Patents
PYRIDINE DERIVATIVES WITH UMAMI FLAVOUR
Publications by Leffingwell & Associates
Flavor Properties of FEMA GRAS List 25 flavor chemicals

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
FDA Listing of Food Additive Status:View
ChemSpider:View

General Material Information

Preferred name 1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one
Trivial Name 1-(2-hydroxy-4-methoxyphenyl)-3-(2-pyridyl)propan-1-one
Formula C15 H15 N O3
CAS Number 1190229-37-8
FEMA Number 4723
FDA UNII EJ17MZ1LNZ
xLogP3-AA 2.60 (est)
NMR Predictor External link
JECFA Food Flavoring 2160 1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 1190229-37-8 ; 1-(2-HYDROXY-4-METHOXYPHENYL)-3-(PYRIDIN-2-YL)PROPAN-1-ONE
Synonyms
  • 1-(2-hydroxy-4-methoxyphenyl)-3-(2-pyridyl)propan-1-one
  • 1-propanone, 1-(2-hydroxy-4-methoxyphenyl)-3-(2-pyridinyl)-

Suppliers

Parchem

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 257.28915405273
Melting Point 65 to 66°C @ 760 mm Hg
Boiling Point 456 to 457°C @ 760 mm Hg
Flash Point TCC Value 230.1 °C TCC
logP (o/w) 2.833 est
Solubility
alcohol Yes
water, 3969 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Savory
General comment Sweet savory
Flavor Type: Salty
umami, sweet, salty, savory
General comment At 2.00 ppm in 0.3% salt solution. umami sweet salty savory

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 1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one 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: 25
Click here to view publication 25
average usual ppmaverage maximum ppm
baked goods: 2.0000025.00000
beverages(nonalcoholic): --
beverages(alcoholic): --
breakfast cereal: --
cheese: 5.0000025.00000
chewing gum: --
condiments / relishes: 2.0000025.00000
confectionery froastings: --
egg products: --
fats / oils: --
fish products: 2.000002.00000
frozen dairy: --
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: 5.0000025.00000
hard candy: --
imitation dairy: 5.0000025.00000
instant coffee / tea: --
jams / jellies: --
meat products: 5.0000025.00000
milk products: --
nut products: --
other grains: --
poultry: 5.000005.00000
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: 5.0000050.00000
snack foods: 5.0000025.00000
soft candy: --
soups: --
sugar substitutes: 5.0000025.00000
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 :49869549
National Institute of Allergy and Infectious Diseases:Data
1-(2-hydroxy-4-methoxyphenyl)-3-(2-pyridyl)propan-1-one
Chemidplus:1190229378