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FEMA 3148, also known as Ethyl (2E,4Z)-2,4-Decadienoate, is a natural aroma compound that has a characteristic pear-like flavor and a light fruity aroma. It is a clear colorless to yellowish liquid that is found in various fruits such as apple, pear, grape, pear brandy, and quince. It is synthesized from (Z)-1-heptenyl bromide, which is converted into a 1-heptenyllithium cuprate complex with lithium and copper iodide, and then reacted with ethyl propiolate to yield a mixture of ethyl (2E,4Z)and ethyl (2E,4E)-2,4-decadienoate. Pure Ethyl (2E,4Z)-2,4-Decadienoate is obtained by fractional distillation, and a biotechnological process for its preparation has also been developed.

3025-30-7

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3025-30-7 Usage

Uses

Used in Flavor and Fragrance Industry:
FEMA 3148 is used as a flavoring agent for enhancing the profile of various fruits such as guava, melon, pear, apple, banana, kiwi, grape, golden delicious apple, fruit cocktail juices, fruit nectar, mamey, and other tropical backgrounds. It imparts a sweet ripe pear, creamy, and slightly fatty aroma with fruity, green, waxy apple, and fleshy nuances.
Used in Food and Beverage Industry:
FEMA 3148 is used as a flavor enhancer in food and beverage products to impart a natural fruity aroma and taste. It is particularly useful in products that require a ripe pear or apple flavor, such as fruit juices, nectars, and other fruit-based beverages.
Used in Cosmetic and Personal Care Industry:
FEMA 3148 is used as a fragrance ingredient in cosmetic and personal care products to provide a fresh, fruity, and slightly fatty scent. It can be used in products such as perfumes, body lotions, and shower gels to create a pleasant and natural aroma experience.
Aroma Threshold Values:
Detection: 100 ppb
Aroma characteristics at 1.0%: sweet ripe pear, creamy and slightly fatty with fruity, green, waxy apple, fleshy nuances.

Synthesis Reference(s)

Tetrahedron, 36, p. 1961, 1980 DOI: 10.1016/0040-4020(80)80209-2

Biochem/physiol Actions

Odor at 1.0%

Synthesis

Synthetically via the lithium vinyl cuprates.

Check Digit Verification of cas no

The CAS Registry Mumber 3025-30-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,0,2 and 5 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 3025-30:
(6*3)+(5*0)+(4*2)+(3*5)+(2*3)+(1*0)=47
47 % 10 = 7
So 3025-30-7 is a valid CAS Registry Number.
InChI:InChI=1/C12H20O2/c1-3-5-6-7-8-9-10-11-12(13)14-4-2/h8-11H,3-7H2,1-2H3/b9-8-,11-10+

3025-30-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name ethyl (2E,4Z)-deca-2,4-dienoate

1.2 Other means of identification

Product number -
Other names EINECS 221-178-8

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3025-30-7 SDS

3025-30-7Relevant articles and documents

Stereoselective synthesis of pear ester

Shakhmaev,Sunagatullina, A. Sh,Akimova,Zorin

, p. 1017 - 1019 (2017)

A simple two-step synthesis of ethyl-(2E,4Z)-deca-2,4-dienoate based on Fe-catalyzed cross-coupling of ethyl-(2E,4Z)-5-chloropenta-2,4-dienoate, which was obtained via one-pot oxidation and olefination of readily available (2Z)-3-chloroprop-2-en-1-ol by n-pentylmagnesiumbromide, was developed.

Preparation method of (E, Z)-2, 4-ethyl decadienoate

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Paragraph 0046; 0047, (2019/05/15)

The invention provides a preparation method of (E, Z)-2, 4-ethyl decadienoate. According to the preparation method, n-hexyl aldehyde is taken as an initial raw material, and three step chemical conversion is adopted to prepare a key intermediate 1-bromo heptene; 1-bromo heptene and ethyl acrylate are subjected to coupling reaction under the catalytic effect of a metal catalyst so as to obtain (E,Z)-2, 4-ethyl decadienoate. According to the preparation method, metal catalytic coupling reaction is adopted to replace a step in the prior art that (E, Z)-2, 4-ethyl decadienoate is prepared throughpreparation of an organic copper lithium reagent, water-free oxygen-free harsh conditions are avoided, operation is simplified, reaction efficiency is increased, generation of waste water and waste salt is reduced greatly, equipment investment is reduced, and the preparation method is convenient for industrialization production.

Bisexual attractants, aggregants and arrestants for adults and larvae of codling moth and other species of lepidoptera

-

, (2008/06/13)

Novel bisexual attractants for lepidopterous insect pests isolated from pears or apples. A method for monitoring and control of codling moth and other species of Lepidoptera comprising a lure and kill, mating disruption or mass trapping strategy. A method of using a formulation containing the bisexual attractants with or without an insecticide and/or pheromone for control of the insect pests.

Stereoselective synthesis of methyl and ethyl (2E,4Z)-2,4-decadienoates from (E)-4,4-dimethoxy-2-butenal

Ovanesyan,Garibyan,Badanyan

, p. 951 - 954 (2007/10/03)

Methyl and ethyl (2E,4Z)-2,4-decadienoates were synthesized starting from (E)-4,4-dimethoxy-2-butenal.

Highly cis-selective Wittig reactions employing α-heterosubstituted ylids

Zhang, Xin-Ping,Schlosser, Manfred

, p. 1925 - 1928 (2007/10/02)

1-Alkenyl chlorides, bromides or iodides can be obtained with very high cis selectivities through Wittig reaction employing α-chloro, α-bromo α-iodo ylids derive from tris(2-methoxymethoxyphenyl)phospine. The corresponding α-methoxy substituted ylid produces enethers with again remarkably high cis/trans ratios. Palladium(II) catalyzed coupling of (Z)-1-iodo-1-heptene with ethyl acrylate affords ethyl (2E,4Z)-2-4-decadienoate, the Bartlett pear fragrance, with almost quantitative yield.

A Stereoselective Synthesis of Ethyl (2E,4Z)-2,4-Decadienoate: Pear Ester

Sharma, G.V.M.,Rajagopal, D.

, p. 633 - 636 (2007/10/02)

A stereoselective synthesis of ethyl (2E,4Z)-2,4-decadienoate (1) is reported from E-pent-2-en-4-yn-1-ol in five steps.

A STEREOSELECTIVE SYNTHESIS OF PEAR ESTER VIA ARSENIC YLIDE

Zhengming, Li,Tiansheng, Wang,Diankun, Zhang,Zhengheng, Gao

, p. 91 - 96 (2007/10/02)

The paper describes a four-step synthesis of ethyl (2E,4Z)-2,4-decadienoate (pear ester) from propargyl alcohol with a 50percent total yield.It also gives the synthesis of ethyl (2E,4E)-2,4-decadienoate.In both cases arsenic ylides were used to give the satisfactory results.

SYNTHESE STEREOSELECTIVE DU DECADIENE-2(E), 4(Z)OATE D'ETHYLE. A PARTIR D'UN MONOACETAL DU GLYOXAL

Stambouli, A.,Amouroux, R.,Chastrette, M.

, p. 5301 - 5302 (2007/10/02)

The glyoxal monoacetal 2, now readily available in bulk quantity, is a very useful synthon for the dienes-1,3 synthesis, as illustrated in the stereoselective preparation of ethyl 2E,4Z-decadienoate using two Wittig-type olefination reactions.

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