EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

ethyl crotonate

Supplier Sponsors

Name:ethyl but-2-enoate
CAS Number: 10544-63-5Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:234-125-9
Beilstein Number:1720418
CoE Number:2244
XlogP3-AA:1.30 (est)
Molecular Weight:114.14410000
Formula:C6 H10 O2
NMR Predictor:Predict (works with chrome or firefox)
Also(can) Contains:ethyl (E)-2-crotonate
Category:flavor and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
JECFA Food Flavoring:1806 ethyl trans-2-butenoate
FEMA Number:3486 ethyl trans-2-butenoate
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Regulation:
FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION
Subpart F--Flavoring Agents and Related Substances
Sec. 172.515 Synthetic flavoring substances and adjuvants.
 
Physical Properties:
Appearance:colorless clear liquid (est)
Assay: 98.00 to 100.00
Food Chemicals Codex Listed: Yes
Specific Gravity:0.91400 to 0.92000 @ 20.00 °C.
Pounds per Gallon - (est).: 7.614 to 7.664
Refractive Index:1.42300 to 1.42800 @ 20.00 °C.
Boiling Point: 136.00 to 137.00 °C. @ 760.00 mm Hg
Acid Value: 2.00 max. KOH/g
Vapor Pressure:6.866000 mm/Hg @ 25.00 °C. (est)
Flash Point: 36.00 °F. TCC ( 2.22 °C. )
logP (o/w): 1.806 (est)
Soluble in:
 alcohol
 water, slightly
 water, 4259 mg/L @ 25 °C (est)
Insoluble in:
 water
Similar Items:note
allyl crotonate
isoamyl crotonate
apple crotonate
benzyl crotonate
butyl (E)-2-crotonate
citronellyl crotonate
cyclohexyl crotonate
dimethyl benzyl carbinyl crotonate
ethyl (E)-2-crotonate
fig crotonate
geranyl crotonate
heptyl crotonate
(Z)-3-hexen-1-yl (E)-crotonate
(E)-3-hexen-1-yl crotonate
hexyl (E)-crotonate
octyl crotonate
phenethyl crotonate
3-phenyl propyl crotonate
plum crotonate
isopropyl (E)-crotonate
propyl crotonate
isopropyl 3-methyl thiocrotonate
 
Organoleptic Properties:
Odor Type: fermented
Odor Strength:medium ,
recommend smelling in a 10.00 % solution or less
pungent fruity acidic estery
Odor Description:at 10.00 % in dipropylene glycol. pungent fruity acrid ester
pungent sharp rummy cognac pineapple fruity meaty
Odor Description:Pungent, sharp, rum- and cognac-Iike, wth tinny, pineapple, fruity and meaty nuances
Mosciano, Gerard P&F 20, No. 6, 49, (1995)
Flavor Type: rummy
rummy cognac pungent caramellic fruity
Taste Description: at 10.00 ppm. Rum, cognac and pungent with caramellic and fruity nuances
Mosciano, Gerard P&F 20, No. 6, 49, (1995)
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: perfuming agents
 
Suppliers:
Apple Flavor & Fragrance
Ethyl crotonate
Diffusions Aromatiques
ETHYL CROTONATE
Ernesto Ventós
ETHYL CROTONATE
Godavari Biorefineries
Ethyl Crotonate
Grau Aromatics
ETHYL-CROTONATE FCC
NI, Kosher
Indukern F&F
ETHYL CROTONATE
Odor: ETHEREAL, POWERFUL, FRUITY
Inoue Perfumery
ETHYL CROTONATE
Kingchem Laboratories
ETHYL CROTONATE (T2 BUTENOATE)
Odor: Sweet, ethereal
Lluch Essence
ETHYL CROTONATE
Odor: FRUITY, GASSY
SRS Aromatics
ETHYL CROTONATE FCC
WholeChem
Ethyl crotonate
 
Safety Information:
European information :
Most important hazard(s):
Xi - Irritant
R 11 - Highly flammable.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 16 - Keep away from sources of ignition - No Smoking.
S 23 - Do not breath vapour.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
 
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 LD50 3000 mg/kg
Nippon Eiseigaku Zasshi. Japanese Journal of Hygiene. Vol. 34, Pg. 183, 1979.

Dermal Toxicity:
skin-guinea pig LD50 > 10 mL/kg
Journal of Industrial Hygiene and Toxicology. Vol. 26, Pg. 269, 1944.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: flavor and fragrance agents
Recommendation for ethyl crotonate usage levels up to:
  6.0000 % in the fragrance concentrate.
 
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: 10
 average usual ppmaverage maximum ppm
baked goods: -20.70000
beverages(nonalcoholic): -3.00000
beverages(alcoholic): -4.00000
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: -16.10000
egg products: --
fats / oils: --
fish products: --
frozen dairy: -8.40000
fruit ices: -8.40000
gelatins / puddings: -5.71000
granulated sugar: --
gravies: --
hard candy: --
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
Env. Mutagen Info. Center:Search
EPA Substance Registry Services (TSCA):10544-63-5
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :12191
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
ethyl but-2-enoate
Chemidplus:0010544635
EPA/NOAA CAMEO:hazardous materials
 
References:
 ethyl but-2-enoate
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:10544-63-5
Pubchem (cid):12191
Pubchem (sid):135018036
Pherobase:View
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Everything Added to Food in the United States (EAFUS):View
HMDB (The Human Metabolome Database):HMDB39581
FooDB:FDB019204
YMDB (Yeast Metabolome Database):YMDB01379
Export Tariff Code:2916.19.7000
Haz-Map:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
For Odor
alcoholic
fusel oil
FL/FR
balsamic
iso
amyl pyruvate
FL/FR
buttery
iso
butyl lactate
FL/FR
caramellic
maltyl propionate
FL/FR
strawberry furanone
FL/FR
cheesy
heptanoic acid
FL/FR
citrus
bitter
orange peel oil brazil
FL/FR
creamy
butyl lactate
FL/FR
ethereal
decyl propionate
FL/FR
ethyl formate
FL/FR
ethyl pyruvate
FL/FR
propyl formate
FL/FR
fermented
iso
butyl decanoate
FL/FR
butyl laevo-lactate
FL/FR
hexanal diethyl acetal
FL/FR
3-
methyl-1-pentanol
FL/FR
floral
ethyl hydrocinnamate
FL/FR
papaya isobutyrate
FL/FR
fruity
iso
amyl nonanoate
FL/FR
iso
butyl acetoacetate
FL/FR
cyclohexanone diethyl acetal
FL/FR
diethyl laevo-tartrate
FL/FR
ethyl (E)-3-hexenoate
FL/FR
ethyl 2-hexenoate
FL/FR
ethyl butyrate
FL/FR
ethyl heptanoate
FL/FR
ethyl propionate
FL/FR
farnesyl acetone
FL/FR
fruity carboxylate
FR
geranyl acetoacetate
FL/FR
4-
heptanone
FL/FR
methyl propionate
FL/FR
2-
phenyl propyl butyrate
FL/FR
prenyl formate
FL/FR
sorbyl butyrate
FL/FR
styryl acetate
FL/FR
green
(E)-2-
hexen-1-yl formate
FL/FR
(E)-2-
hexen-1-yl valerate
FL/FR
herbal
6-
acetoxydihydrotheaspirane
FL/FR
anthemis nobilis flower oil roman
FL/FR
clary sage concrete
FL/FR
white
cognac oil
FL/FR
honey
allyl phenyl acetate
FL/FR
soapy
ethyl undecanoate
FL/FR
sulfurous
grapefruit menthane
FL/FR
waxy
iso
amyl laurate
FL/FR
butyl laurate
FL/FR
ethyl nonanoate
FL/FR
ethyl octanoate
FL/FR
winey
butyl angelate
FL/FR
2-
hexanol
FL/FR
For Flavor
No flavor group found for these
6-
acetoxydihydrotheaspirane
FL/FR
iso
amyl pyruvate
FL/FR
2-
amyl-5 or 6-keto-1,4-dioxane
FL
butyl angelate
FL/FR
iso
butyl decanoate
FL/FR
iso
butyraldehyde propylene glycol acetal
FL
cyclohexanone diethyl acetal
FL/FR
decyl propionate
FL/FR
diethyl laevo-tartrate
FL/FR
ethyl 2-hexenoate
FL/FR
ethyl aconitate
FL
ethyl hydrocinnamate
FL/FR
farnesyl acetone
FL/FR
geranyl acetoacetate
FL/FR
hexanal diethyl acetal
FL/FR
2-
hexanol
FL/FR
prenyl formate
FL/FR
styryl acetate
FL/FR
buttery
buttery
iso
butyl lactate
FL/FR
butyl laevo-lactate
FL/FR
caramellic
5-
ethyl-3,4,5,6-tetramethyl cyclohexen-2-one
FL
maltyl propionate
FL/FR
strawberry furanone
FL/FR
coffee
2-iso
propyl pyrazine
FL
dairy
butyl lactate
FL/FR
earthy
1-
hexen-3-yl acetate
FL
ethereal
ethyl formate
FL/FR
fatty
iso
amyl laurate
FL/FR
fruity
iso
butyl acetoacetate
FL/FR
ethyl (E)-3-hexenoate
FL/FR
ethyl butyrate
FL/FR
ethyl heptanoate
FL/FR
ethyl propionate
FL/FR
fusel oil
FL/FR
4-
heptanone
FL/FR
methyl propionate
FL/FR
bitter
orange peel oil brazil
FL/FR
propyl formate
FL/FR
sorbyl butyrate
FL/FR
fusel
white
cognac oil
FL/FR
green
(E)-2-
hexen-1-yl valerate
FL/FR
4-
methyl-2-pentenal
FL
papaya isobutyrate
FL/FR
herbal
anthemis nobilis flower oil roman
FL/FR
clary sage concrete
FL/FR
honey
allyl phenyl acetate
FL/FR
rummy
ethyl pyruvate
FL/FR
(E)-2-
hexen-1-yl formate
FL/FR
spicy
2-
phenyl propyl butyrate
FL/FR
sulfurous
grapefruit menthane
FL/FR
waxy
butyl laurate
FL/FR
ethyl nonanoate
FL/FR
ethyl octanoate
FL/FR
ethyl undecanoate
FL/FR
heptanoic acid
FL/FR
whiskey
3-
methyl-1-pentanol
FL/FR
winey
iso
amyl nonanoate
FL/FR
 
Potential Uses:
FRblueberry
FRcherry
FRcitrus
FRcucumber
FRguava
FRorange
FRraspberry
FRstrawberry
 
Occurrence (nature, food, other):note
 guava fruit
Search Trop Picture
 michelia figo
Search Trop Picture
 passion fruit yellow
Search Trop Picture
 strawberry wild strawberry fruit
Search Trop Picture
 wine white wine
Search Picture
 
Synonyms:
2-butenoic acid ethyl ester
2-butenoic acid, ethyl ester
 crotonic acid ethyl ester
 ethyl 2-butenoate
 ethyl but-2-enoate
 ethyl crotonate (T2 butenoate)
 ethyl-2-butenoate
 ethyl-crotonate FCC
 

Articles:

PubMed:Isolation and identification of host cues from mango, Mangifera indica, that attract gravid female oriental fruit fly, Bactrocera dorsalis.
PubMed:Gas-phase oxidation of methyl crotonate and ethyl crotonate. kinetic study of their reactions toward OH radicals and Cl atoms.
PubMed:Phospha-Michael additions to activated internal alkenes: steric and electronic effects.
PubMed:Aroma volatiles recovered in the water phase of cashew apple (Anacardium occidentale L.) juice during concentration.
PubMed:Effects of methanogenic inhibitors on methane production and abundances of methanogens and cellulolytic bacteria in in vitro ruminal cultures.
PubMed:The role of an aromatic group in remote chiral induction during conjugate addition of alpha-sulfonylallylic carbanions to ethyl crotonate.
PubMed:Enantioselective organocatalytic double Michael addition reactions.
PubMed:Synthesis and characterization of zinc AP-MOCVD precursors and their utility in the growth of ZnO.
PubMed:Gas-phase reactivity of the O=P(OCH3)2 + phosphonium ion towards alpha,beta-unsaturated esters in a quadrupole ion trap.
PubMed:Synthesis of a novel plant growth promoter from gallic acid.
PubMed:A modular and concise total synthesis of (+/-)-daurichromenic acid and analogues.
PubMed:Synthesis of enantiomerically pure 2,2,3,4,5-pentasubstituted pyrrolidines by phenylsulfanyl migration.
PubMed:Stereospecific substitution of enantiomerically pure 1-(2-pyridinyl)ethyl methanesulfonate with beta-dicarbony compounds.
PubMed:Metabolism of ethyl tiglate in apple fruits leads to the formation of small amounts of (R)-ethyl 2-methylbutanoate.
PubMed:Synthesis of 4-methoxy-2,3,5-trimethylpyridine: a specific building block for compounds with gastric-acid inhibiting activity.
PubMed:Fluorinated retinoic acids and their analogues. 3. Synthesis and biological activity of aromatic 6-fluoro analogues.
PubMed:[On the specifity and stereospecificity of the conversion of different 2,3-unsaturated acids by Clostridium kluyveri (author's transl)].
PubMed:Substrate stereochemistry of the enoyl-CoA hydratase reaction.
 
Notes:
Component of strawberry aroma, guava fruit and peel (Psidium guajava), pineapple, yellow passion fruit and other fruits. Also present in white wine and mussels. Flavouring ingredient
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