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ethyl alpha-ethyl-beta-methyl-beta-phenyl glycidate

Ethyl alpha-ethyl-beta-methyl-beta-phenyl glycidate is a synthetic fruity flavor and fragrance agent characterized by a sweet berry aroma and used in food and cosmetic formulations.

General Material Description

Ethyl alpha-ethyl-beta-methyl-beta-phenyl glycidate is a synthetic organic ester classified chemically as an oxirane carboxylate with molecular formula C14H18O3. It appears as a liquid substance with a characteristic sweet fruity berry and jammy aroma, making it valuable in flavor and fragrance formulations. Known also by several synonyms such as ethyl (E)-2-ethyl-3-methyl-3-phenyl oxirane-2-carboxylate, this compound is referenced under FEMA (Flavor and Extract Manufacturers Association) number 4653 and JECFA (Joint FAO/WHO Expert Committee on Food Additives) number 2143. It is typically obtained via chemical synthesis and is not naturally occurring, widely used to impart fruity notes in various consumer goods. Its entry in public chemical databases like PubChem provides detailed chemical and safety information.

Occurrence, Applicability & Potential Uses

This compound is not found naturally but is manufactured specifically for use as a flavor and fragrance agent. Its fruity and berry-like sensory properties allow it to enhance or impart sweet, vibrant notes in foods, beverages, and personal care products. It is utilized in formulations for chewing gum, nonalcoholic beverages, confections, and gelatins, with typical concentration limits established by FEMA (US) to ensure safety and consistency. The substance complies with standards such as IFRA (International Fragrance Association) (Global) guidelines, governing use levels in perfumes and cosmetic applications. Its incorporation in flavor systems delivers complex fruity nuances, complementing other aroma chemicals in diverse product categories.

Physico-Chemical Properties Summary

Ethyl alpha-ethyl-beta-methyl-beta-phenyl glycidate exhibits melting points ranging from 37 to 42°C and boiling points between 295 and 297°C at standard atmospheric pressure (760 mm Hg). Its vapor pressure is very low, about 0.001 mmHg at 25°C, indicating low volatility under ambient conditions. The estimated partition coefficient (log P) is approximately 3.5, reflecting moderate hydrophobicity. It is soluble in alcohol solvents but has limited solubility in water, with an estimated aqueous solubility of 12.33 mg/L at 25°C. The compound’s flash point is reported at 248°F (approximately 120°C), consistent with its use as a stable ingredient in fragrant and flavor formulations. These properties affect its evaporation rate, blending behavior, and compatibility in various media.

FAQ

What is ethyl alpha-ethyl-beta-methyl-beta-phenyl glycidate and what are its primary uses?
Ethyl alpha-ethyl-beta-methyl-beta-phenyl glycidate is a synthetic organic compound used primarily as a flavor and fragrance agent. It imparts fruity, sweet berry, and jammy aroma notes, making it valuable in the flavoring and perfumery industries. Common applications include incorporation in chewing gum, beverages, confections, and personal care products where these sensory profiles are desirable.
How is ethyl alpha-ethyl-beta-methyl-beta-phenyl glycidate produced and where does it occur naturally?
This compound is produced via chemical synthesis; it does not occur naturally in any significant biological sources. Its manufacture involves esterification and epoxidation processes to form the oxirane carboxylate ester structure. Synthetic origin ensures controlled purity and consistency for industrial applications in flavors and fragrances.
What regulatory standards apply to ethyl alpha-ethyl-beta-methyl-beta-phenyl glycidate and are there safety considerations?
Ethyl alpha-ethyl-beta-methyl-beta-phenyl glycidate is recognized under FEMA (US) number 4653 and JECFA (FAO/WHO) number 2143 for use as a flavoring substance. It is evaluated as Generally Recognized As Safe (GRAS) when used within established use levels. IFRA (Global) provides guidelines for fragrance use, defining concentration limits to ensure consumer safety. Hazard classifications according to OSHA HCS standards show no significant hazards identified. Safety assessments recommend adherence to usage limits specified in these codes to avoid adverse effects.

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
ChemSpider:View

General Material Information

Trivial Name ethyl alpha-ethyl-beta-methyl-beta-phenyl glycidate
Short Description ethyl alpha-ethyl-beta-methyl-beta-phenylglycidate
Formula C14 H18 O3
CAS Number 19464-94-9
FEMA Number 4653
FDA UNII 150T1N4DFJ
Nikkaji Number J104.291B
xLogP3-AA 2.60 (est)
NMR Predictor External link
JECFA Food Flavoring 2143 ethyl alpha-ethyl-beta-methyl-beta-phenylglycidate
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 56630-76-3 ; ETHYL ALPHA-ETHYL-BETA-METHYL-BETA-PHENYLGLYCIDATE
Synonyms
  • alpha,beta- epoxy-alpha-ethyl-beta-methyl hydrocinnamic acid ethyl ester
  • ethyl (E)-2-ethyl-3-methyl-3-phenyl oxirane-2-carboxylate
  • ethyl (E)-2-ethyl-3-methyl-3-phenyloxirane-2-carboxylate
  • ethyl 2-ethyl-3-methyl-3-phenyl-2-oxiranecarboxylate
  • ethyl 2-ethyl-3-methyl-3-phenyloxirane-2-carboxylate
  • ethyl a-ethyl-b-methyl-b-phenylglycidate
  • ethyl alpha-ethyl-beta-methyl-beta-phenylglycidate
  • ethyl trans-2-ethyl-3-methyl-3-phenyloxirane-2-carboxylate
  • (E)-2-ethyl-3-methyl-3-phenyl oxiranecarboxylic acid ethyl ester
  • trans-2-ethyl-3-methyl-3-phenyl oxiranecarboxylic acid ethyl ester
  • oxiranecarboxylic acid, 2-ethyl-3-methyl-3-phenyl-, ethyl ester

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 234.2950592041
Melting Point 37 to 42°C @ 760 mm Hg
Boiling Point 295 to 297°C @ 760 mm Hg
Vapor Pressure 0.001 mmHg @ 25 °C
Flash Point TCC Value 120 °C TCC
logP (o/w) 3.5 est
Solubility
alcohol Yes
water, 12.33 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Fruity
fruity, berry, jammy, raspberry, strawberry
General comment At 100.00 %. sweet fruity berry jammy
Flavor Type: Fruity
fruity, berry, tutti frutti
General comment Fruity berry tutti frutti

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:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
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): 0.100005.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: 5.0000050.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: --
fruit ices: --
gelatins / puddings: 0.300005.00000
granulated sugar: --
gravies: --
hard candy: 1.0000020.00000
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 ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :569008
National Institute of Allergy and Infectious Diseases:Data
ethyl 2-ethyl-3-methyl-3-phenyloxirane-2-carboxylate
Chemidplus:0019464949