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Ethyl 2-trans-4-cis-decadienoate

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CAS:3025-30-7
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Products Intro: Product Name:Ethyl (2E,4Z)-deca-2,4-dienoate
CAS:3025-30-7
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Ethyl 2-trans-4-cis-decadienoate Basic information
Product Name:Ethyl 2-trans-4-cis-decadienoate
Synonyms:ethyltrans-2-cis-4-decandienoate,mixtureofisomers;trans,cis-deca-2,4-dienoicacidethylester;(2E,4Z)-PEAR ESTER;ETHYL 2,4-DECADIENOATE;ETHYL (2E,4Z)-DECADIENOATE;ETHYL 2-TRANS-4-CIS-DECADIENOATE;FEMA 3148;ETHYL TRANS-2,CIS-4-DECADIENOATE
CAS:3025-30-7
MF:C12H20O2
MW:196.29
EINECS:221-178-8
Product Categories:Building Blocks;C12 to C63;Carbonyl Compounds;Chemical Synthesis;Esters;Organic Building Blocks;Alphabetical Listings;Certified Natural ProductsFlavors and Fragrances;E-F;Flavors and Fragrances
Mol File:3025-30-7.mol
Ethyl 2-trans-4-cis-decadienoate Structure
Ethyl 2-trans-4-cis-decadienoate Chemical Properties
Melting point -60 °C
Boiling point 70-72 °C0.05 mm Hg(lit.)
density 0.905 g/mL at 25 °C(lit.)
vapor pressure 1.6hPa at 21.1℃
FEMA 3148 | ETHYL TRANS-2,CIS-4-DECADIENOATE
refractive index n20/D 1.486(lit.)
Fp >230 °F
storage temp. 2-8°C
solubility Chloroform (Slightly), Methanol (Slightly)
color Colourless
Odorat 10.00 % in dipropylene glycol. green waxy pear apple sweet fruity tropical
Odor Typegreen
JECFA Number1192
BRN 1724176
LogP4.1-4.7 at 35℃ and pH7
EPA Substance Registry System2,4-Decadienoic acid, ethyl ester, (2E,4Z)- (3025-30-7)
Safety Information
Hazard Codes Xi,N
Risk Statements 38-50/53
Safety Statements 24/25-61-60
RIDADR UN 3082 9/PG 3
WGK Germany 1
RTECS HD3510900
10-23
HS Code 29161995
ToxicityLD50 oral in rat: > 5gm/kg
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
Ethyl 2-trans-4-cis-decadienoate Usage And Synthesis
Chemical PropertiesEthyl-trans-2, cis-4-decadienoate has a characteristic pear-like flavor and a light fruity aroma.
Chemical Properties Ethyl (2E,4Z)-2,4-Decadienoate (Ethyl 2-trans-4-cis-decadienoate) has been identified in pears and has the typical aroma of Williams pears. Synthesis of ethyl (2E,4Z)-2,4-decadienoate starts from (Z)-1-heptenyl bromide, which is converted into a 1-heptenyllithium cuprate complex with lithium and copper iodide. Reaction with ethyl propiolate yields a mixture of 95% ethyl (2E,4Z)- and 5% ethyl (2E,4E)-2,4-decadienoate. Pure ethyl (2E,4Z)-2,4-decadienoate is obtained by fractional distillation. A biotechnological process for its preparation has been developed.
Chemical Propertiesclear colorless to yellowish liquid
OccurrenceReported found in Bartlett pears, apple, grape, durian (Durio zibethinus), pear brandy, quince and spineless monkey orange (Strychnos madagasc).
Uses The potential applications of Ethyl 2-trans-4-cis-decadienoate include the profile enhancement of guava, melon, pear, apple, banana, kiwi, grape, golden delicious apple, fruit cocktail juices, fruit nectar, mamey and other tropical backgrounds.
Ethyl 2-trans-4-cis-decadienoate (DDSE) is a flavoring that is largely responsible for the aroma of Williams pears is responsible.
Definition Ethyl (2E,4Z)-deca-2,4-dienoate (Ethyl 2-trans-4-cis-decadienoate) is a fatty acid ethyl ester resulting from the formal condensation of the carboxy group of (2E,4E)-deca-2,4-dienoic acid with the hydroxy group of ethanol. It has a role as a plant metabolite, a flavouring agent, a fragrance and a kairomone. It is a natural product found in Euglena gracilis.
Production Methods Stillingia oil is one of the fruits of the tallow tree native to China (Stillingia sebifera or Sapium sepiferum, Euphorbiaceae) vegetable fat. It contains about 5% of DDS in the form of glycerides by weight. Ethyl 2-trans-4-cis-decadienoate (DDSE) can be obtained from this by base-catalyzed transesterification with ethanol; however, in food law, this is not a natural process, so the product obtained cannot be called a natural flavouring.
A mixture of Stillingia oil (5 kg), natural ethanol (1.0 kg) and Novozym 435 (1.0 kg) was overlaid with nitrogen in a 20-liter glass vessel at 45 ° C and slowly stirred. The vessel was fitted with a water cooler to prevent losses and minimize evaporation. The approach was cancelled after an incubation period of 2 to 3 each Day. The filtered enzyme was added with fresh Stillingia oil and natural ethanol, and stirring was continued. All 10 cycles were performed, the content of Ethyl 2-trans-4-cis-decadienoate from the individual filtrates varied between 4.0 and 4.7% by weight.
Aroma threshold valuesDetection: 100 ppb. Aroma characteristics at 1.0%: sweet ripe pear, creamy and slightly fatty with fruity, green, waxy apple, fleshy nuances
Taste threshold valuesTaste characteristics at 5 ppm: ripe pear, green fruity, waxy apple, tropical notes, fatty golden delicious apple fleshy. Taste characteristics at 20 ppm: green, fruity, apple and pear with waxy tropical nuances.
Synthesis Reference(s)Tetrahedron, 36, p. 1961, 1980 DOI: 10.1016/0040-4020(80)80209-2
General DescriptionNatural occurrence: Apple, pear, grape, pear brandy and quince.
Biochem/physiol ActionsOdor at 1.0%
SynthesisSynthetically via the lithium vinyl cuprates.
Ethyl 2-trans-4-cis-decadienoate Preparation Products And Raw materials
Raw materialsLithium carbonate
Preparation Productsdecadienal,(E,Z)-2,4-decadienal
Tag:Ethyl 2-trans-4-cis-decadienoate(3025-30-7) Related Product Information
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