2-butyl-2-butenal

2-butyl-2-butenal, also known by its synonym 2-ethylidenehexanal, is an aliphatic aldehyde with the molecular formula C₈H₁₄O. This compound appears as a colorless liquid with a distinctive roasted and sweet nutty aroma, contributing to its use as a flavoring agent. Related synonyms include 2-butyl but-2-enal and (2Z)-2-ethylidenehexanal. It belongs to the class of unsaturated aldehydes and is found in natural and synthetic flavor formulations. Structural and chemical data for 2-butyl-2-butenal are documented in the PubChem database. The compound is primarily obtained through chemical synthesis to meet flavor industry standards.

2-butyl-2-butenal occurs in nature as part of complex flavor profiles and is synthesized for its application as a flavoring agent. It is predominantly used to impart roasted and nutty flavors in food products, with specific utility in meat and nut flavor formulations. The compound's use is evaluated and authorized under standards such as FEMA (US), which assigns it number 3392, confirming its status as a recognized flavoring substance. Its inclusion in various food categories is guided by usage limits based on safety assessments.

The compound is a colorless liquid with a molecular weight of approximately 126.2 g/mol and a molecular formula of C₈H₁₄O. It has a boiling point range between 182 and 183 °C at atmospheric pressure (760 mm Hg), which indicates moderate volatility appropriate for flavor applications requiring thermal stability. Its vapor pressure at 25 °C is about 0.805 mmHg, supporting controlled evaporation in formulations. The specific gravity is around 1.449 to 1.459 at 20 °C, and the refractive index falls between 1.447 and 1.453. The estimated log P value of approximately 2.7 suggests moderate lipophilicity, facilitating solubility in alcohol but limited solubility in water. These physico-chemical properties influence the compound's behavior in flavor mixtures and food matrices, affecting release and perception in sensory use.

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
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(IUPAC):	Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):	View
HMDB (The Human Metabolome Database):	HMDB37152
FooDB:	FDB016147
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:
flavoring agents
Recommendation for 2-butyl-2-butenal usage levels up to:
	not for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU):		0.02 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA):		0.01 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI):		1700 (μg/person/day)
Threshold of Concern:		90 (μg/person/day)
Structure Class:		III
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: 7
Click here to view publication 7
		average usual ppm	average maximum ppm
baked goods:		-	2.00000
beverages(nonalcoholic):		-	0.50000
beverages(alcoholic):		-	-
breakfast cereal:		-	-
cheese:		-	-
chewing gum:		-	-
condiments / relishes:		-	-
confectionery froastings:		-	-
egg products:		-	-
fats / oils:		-	-
fish products:		-	-
frozen dairy:		-	0.60000
fruit ices:		-	0.60000
gelatins / puddings:		-	1.50000
granulated sugar:		-	-
gravies:		-	-
hard candy:		-	1.50000
imitation dairy:		-	-
instant coffee / tea:		-	-
jams / jellies:		-	-
meat products:		-	-
milk products:		-	0.60000
nut products:		-	-
other grains:		-	-
poultry:		-	-
processed fruits:		-	-
processed vegetables:		-	-
reconstituted vegetables:		-	-
seasonings / flavors:		-	-
snack foods:		-	-
soft candy:		-	-
soups:		-	-
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/kg	maximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0):		5.03000	11.86000
Fats and oils, and fat emulsions (type water-in-oil) (02.0):		0.50000	4.00000
Edible ices, including sherbet and sorbet (03.0):		0.50000	2.75000
Processed fruit (04.1):		-	-
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2):		4.78000	5.00000
Confectionery (05.0):		5.00000	14.22000
Chewing gum (05.3):		2.20000	9.56000
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0):		3.79000	11.40000
Bakery wares (07.0):		6.20000	17.17000
Meat and meat products, including poultry and game (08.0):		0.79000	3.50000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0):		0.50000	1.75000
Eggs and egg products (10.0):		0.01000	3.00000
Sweeteners, including honey (11.0):		0.51000	4.38000
Salts, spices, soups, sauces, salads, protein products, etc. (12.0):		1.75000	5.00000
Foodstuffs intended for particular nutritional uses (13.0):		0.01000	5.01000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1):		2.00000	4.43000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2):		1.00000	2.00000
Ready-to-eat savouries (15.0):		2.00000	3.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0):		0.50000	0.50000

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 201: 2-Alkylated aliphatic acyclic alpha,beta-unsaturated aldehydes and precursors with or without additional double bonds from chemical subgroup 1.1.2 of FGE.19[1] View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 201 Revision 1 (FGE.201Rev1): 2-Alkylated, aliphatic, acyclic alpha,beta-unsaturated aldehydes and precursors, with or without additional double-bonds, from chemical subgroup 1.1.2 of FGE.19. View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 201 Revision 2 (FGE.201Rev2): 2-alkylated, aliphatic, acyclic alpha,beta-unsaturated aldehydes and precursors, with or without additional double-bonds, from chemical subgroup 1.1.2 of FGE.19 View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 72, Revision 2 (FGE.72Rev2): consideration of aliphatic, branched-chain saturated and unsaturated alcohols, aldehydes, acids and related esters evaluated by JECFA (61st, 68th and 69th meetings) and structurally related to flavouring substances in FGE.05Rev3 View page or View pdf

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EPA Substance Registry Services (TSCA):25409-08-9

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :53424302

National Institute of Allergy and Infectious Diseases:Data

2-ethylidenehexanal

Chemidplus:0025409089

(2E)-2-ethylidenehexanal

Chemidplus:0087745651

(2Z)-2-ethylidenehexanal