eugenyl benzoate

Eugenyl benzoate is an organic ester classified chemically as phenol, 4-allyl-2-methoxy-, benzoate, with the molecular formula C₁₇H₁₆O₃. It appears as a solid with a characteristic spicy odor reminiscent of mild balsam clove. Among its many synonyms are benzoyl eugenol and 4-allyl-2-methoxyphenyl benzoate. This compound is referenced in controlled-vocabulary resources such as PubChem Compound 62362. Eugenyl benzoate is typically derived by esterification of eugenol with benzoic acid or corresponding derivatives, often sourced from natural oils containing eugenol. This compound is valued in the flavor and fragrance industry for its distinct odor and fixative properties.

Eugenyl benzoate naturally occurs in essential oils including cascarilla oil, perilla, and sage. It is utilized primarily as a flavor and fragrance agent. Its sensory applications include imparting balsam, banana, croton eluteria bark, date, and pear notes. Additionally, it serves as a fixative to enhance fragrance stability and longevity. Regulatory evaluation by FEMA (US) recognizes it with FEMA number 2471 in flavor use, and it features on JECFA (International) as flavoring substance 1533. These assessments guide its safe inclusion levels in consumer products, reflecting its applicability in food flavorings and perfumery formulations.

Eugenyl benzoate exhibits a molecular weight of approximately 268.3 g/mol and a melting point range between 69 and 70°C at atmospheric pressure. It has an estimated octanol-water partition coefficient (log P) of 3.447, indicating moderate lipophilicity. The compound demonstrates very low vapor pressure, around 2.2×10⁻⁵ mmHg at 25°C, suggesting low volatility under ambient conditions. It is soluble in alcohol and shows minimal solubility in water, measured approximately 2.583 mg/L at 25°C. The flash point is relatively high at about 358°F (182°C), contributing to its stability during typical handling and formulation processes. These properties influence its behavior and compatibility in fragrance and flavor preparations.

	(2-methoxy-4-prop-2-enylphenyl) benzoate
NIST Chemistry WebBook:	Search Inchi
Canada Domestic Sub. List:	531-26-0
Pubchem (cid):	62362
Pubchem (sid):	135020175

(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
CHEMBL:	View
HMDB (The Human Metabolome Database):	HMDB32056
FooDB:	FDB008763
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View

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
Recommendation for eugenyl benzoate usage levels up to:
	0.8000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU):		0.0024 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA):		0.90 (μg/capita/day)
Threshold of Concern:		1800 (μg/person/day)
Structure Class:		I
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: 3
Click here to view publication 3
		average usual ppm	average maximum ppm
baked goods:		0.13000	10.00000
beverages(nonalcoholic):		0.03000	0.13000
beverages(alcoholic):		-	-
breakfast cereal:		-	-
cheese:		-	-
chewing gum:		-	-
condiments / relishes:		-	-
confectionery froastings:		-	-
egg products:		-	-
fats / oils:		-	-
fish products:		-	-
frozen dairy:		0.25000	2.00000
fruit ices:		0.25000	2.00000
gelatins / puddings:		-	-
granulated sugar:		-	-
gravies:		-	-
hard candy:		0.25000	10.00000
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

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):

Flavouring Group Evaluation 60 (FGE.60): Consideration of eugenol and related hydroxyallylbenzene derivatives evaluated by JECFA (65th meeting) structurally related to ring- substituted phenolic substances evaluated by EFSA in FGE.22 (2006) View page or View pdf

EPI System: View

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA Substance Registry Services (TSCA):531-26-0

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :62362

National Institute of Allergy and Infectious Diseases:Data

(2-methoxy-4-prop-2-enylphenyl) benzoate

Chemidplus:0000531260