4493-42-9 Usage
Description
2,4-Decadienoic Acid Methyl Ester, also known as (2E,4Z)-2,4-Decadienoic Acid Methyl Ester, is an organic compound with a fruity, waxy, pear-like odor and a slight lemon connotation. It is characterized by its unique chemical structure, featuring two double bonds at the 2nd and 4th carbon positions, which contribute to its distinct properties and applications.
Uses
Used in Chemical Synthesis:
2,4-Decadienoic Acid Methyl Ester is used as a key intermediate in the syntheses of various compounds, such as Methyl (R,E)-2,4,5-tetradecatrienoate and Methyl (2E,4Z)-2,4-decadienoate. These compounds are known to be pheromone components of the male dried bean beetle, Acanthoscelides obtectus (Say), making it an essential component in the study and manipulation of these insects' behaviors.
Used in Flavor and Fragrance Industry:
Due to its fruity, waxy, pear-like odor with a slight lemon connotation, 2,4-Decadienoic Acid Methyl Ester can be used as a flavoring agent or a fragrance ingredient in the food, beverage, and cosmetic industries. Its unique scent profile can be utilized to enhance or create new flavor and fragrance combinations.
Used in Agriculture:
In the agricultural sector, 2,4-Decadienoic Acid Methyl Ester can be employed as a semiochemical to attract or repel specific insect species, such as the dried bean beetle. This application can help in the development of more targeted and environmentally friendly pest control strategies.
Occurrence:
2,4-Decadienoic Acid Methyl Ester has been reported to be found in various natural sources, including pears, pear brandy, and spineless monkey orange. This indicates its potential use in the food and beverage industry as a natural flavoring agent or in the creation of natural fragrances.
Synthesis Reference(s)
Synthetic Communications, 18, p. 77, 1988 DOI: 10.1080/00397918808057822Tetrahedron Letters, 27, p. 603, 1986 DOI: 10.1016/S0040-4039(00)84052-6
Check Digit Verification of cas no
The CAS Registry Mumber 4493-42-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,4,9 and 3 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 4493-42:
(6*4)+(5*4)+(4*9)+(3*3)+(2*4)+(1*2)=99
99 % 10 = 9
So 4493-42-9 is a valid CAS Registry Number.
InChI:InChI=1/C11H18O2/c1-3-4-5-6-7-8-9-10-11(12)13-2/h7-10H,3-6H2,1-2H3/b8-7-,10-9+
4493-42-9Relevant articles and documents
Fe-catalyzed synthesis of methyl-(2E,4Z)-deca-2,4-dienoate, a component of sex pheromones of Pityogenes chalcographus and Acanthoscelides obtectus
Shakhmaev,Sunagatullina, A. Sh.,Akimova,Zorin
, p. 1638 - 1640 (2017)
Stereoselective synthesis of methyl-(2E,4Z)-deca-2,4-dienoate, a component of sex pheromones of Pityogenes chalcographus and Acanthoscelides obtectus, was performed on the basis of Fe-catalyzed cross-coupling of methyl-(2E,4Z)-5-chloropenta-2,4-dienoate with n-pentylmagnesium bromide.
Pheromone synthesis. Part 249: Syntheses of methyl (R,E)-2,4,5- tetradecatrienoate and methyl (2E,4Z)-2,4-decadienoate, the pheromone components of the male dried bean beetle, Acanthoscelides obtectus (Say)
Mori, Kenji
experimental part, p. 1936 - 1946 (2012/04/10)
The enantiomers of methyl (E)-2,4,5-tetradecatrienoate (1), a component of the male pheromone of Acanthoscelides obtectus, were synthesized from the enantiomers of 1-undecyn-3-ol (6), which were obtained via asymmetric acetylation of (±)-1-trimethylsilyl-1-undecyn-3-ol (4) with vinyl acetate as catalyzed by lipase PS (Amano). The ortho ester Claisen rearrangement of 6 with triethyl orthoacetate was the key-step to generate the chiral allenic system. A new synthesis of (±)-1 was also executed starting from (±)-6. Three different syntheses of methyl (2E,4Z)-2,4-decadienoate (2), another component of the male pheromone of A. obtectus, were achieved by means of either palladium-catalyzed Heck reaction or a Claisen and an Al 2O3 catalyzed thermal rearrangements.
EXO- and endohormones. XXII1: Synthesis of methyl (2E,4Z)-2,4-decadienoate, the pheromone synergist of the bark beetle Pityogenes chalcographus
Maxim, Sanda,Ganscǎ, Lucia,Oprean, Ioan,Budae, Iuliana
, p. 543 - 544 (2007/10/03)
The synthesis of methyl (2E,4Z)-2,4-decadienoate was based on a C 4 + C6 scheme. The coupling reaction took place between the 1-hexanale and phosphonium salt of methyl 1-bromocrotonate in a Wittig condensation. Methyl (2E,4Z)-2,4-decadienoate is a minor component of the sex pheromone of the bark beetle Pityogenes chalcographus.
