5837-78-5 Usage
Description
Ethyl tiglate, an α,β-unsaturated ester, is a naturally occurring aroma compound found in various fruits such as apples, strawberries, Vitis species, durian, starfruit, and naranjilla. It is characterized by its liquid state and fruity, caramel odor, with a detection threshold of 65 ppb. Ethyl tiglate can be prepared by the esterification of tiglic acid and is also known as a male-specific pheromone in some Drosophila species, attracting both male and female flies. Additionally, it has been reported that Saprochaete suaveolens, when grown in a culture medium, can produce ethyl tiglate by metabolizing isoleucine.
Uses
Used in Flavor and Fragrance Industry:
Ethyl tiglate is used as a flavor and fragrance ingredient for its fruity, caramel odor. It is particularly valued in the creation of artificial fruit flavors and fragrances due to its natural occurrence in various fruits.
Used in Pheromone Research:
In the field of biological research, ethyl tiglate is used as a pheromone for studying the mating behavior and communication of certain Drosophila species. Its role as a male-specific pheromone makes it an important compound for understanding the chemical ecology and reproductive strategies of these insects.
Used in Chemical Synthesis:
Ethyl tiglate is also utilized in the synthesis of other compounds, such as grandisol and fraganol. These synthesized products have their own specific applications in various industries, further expanding the utility of ethyl tiglate as a starting material in chemical synthesis.
Used in the Study of Microbial Metabolism:
The production of ethyl tiglate by Saprochaete suaveolens through the metabolism of isoleucine provides an opportunity for researchers to study the metabolic pathways and capabilities of this microorganism. This knowledge can be applied to develop new biotechnological applications and improve our understanding of microbial processes.
Preparation
By direct esterification of tiglic acid with ethyl alcohol in the presence of concentrated H2SO4 or by reaction of bromomethylethyl acetic acid ethyl ester with dimethylaniline.
Check Digit Verification of cas no
The CAS Registry Mumber 5837-78-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,8,3 and 7 respectively; the second part has 2 digits, 7 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 5837-78:
(6*5)+(5*8)+(4*3)+(3*7)+(2*7)+(1*8)=125
125 % 10 = 5
So 5837-78-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H12O2/c1-4-6(3)7(8)9-5-2/h4H,5H2,1-3H3/b6-4+
5837-78-5Relevant articles and documents
Asymmetric synthesis of α,β-substituted γ-amino acids via conjugate addition
Sabala, Rocío,Assad, Salomon,Mendoza, ángel,Jiménez, Jacqueline,Sansinenea, Estibaliz,Ortiz, Aurelio
, p. 1741 - 1744 (2019/06/05)
The first conjugate addition reaction of organocuprates to N-enoyl oxazolidinone where a N-protected γ-nitrogen atom and an α-methyl group are present into α, β-unsaturated system is described. This reaction gave anti-products in moderate yields and high diastereomeric ratios. The anti-products have two contiguous stereogenic centers, one formed by the conjugate addition reaction and the other by a diastereoselective protonation reaction. The removal of chiral oxazolidinone moiety and N-deprotection of amino group furnished chiral α, β-disubstituted γ-amino acids.
Highly enantioselective iridium-catalyzed hydrogenation of α,β-unsaturated esters
Li, Jia-Qi,Quan, Xu,Andersson, Pher G.
supporting information, p. 10609 - 10616 (2012/11/07)
α,β-Unsaturated esters have been employed as substrates in iridium-catalyzed asymmetric hydrogenation. Full conversions and good to excellent enantioselectivities (up to 99 % ee) were obtained for a broad range of substrates with both aromatic- and aliphatic substituents on the prochiral carbon. The hydrogenated products are highly useful as building blocks in the synthesis of a variety of natural products and pharmaceuticals. Asymmetric hydrogenation: A variety of α,β-unsaturated esters were hydrogenated with high enantioselectivities (see scheme). The hydrogenated products have been used in synthetic transformations as well as in formal total syntheses. Copyright
Efficient preparation of α,α-dialkyl-α-(phenylselanyl) acetates and α,β-unsaturated esters from the corresponding α,α-dialkyl-α-cyanoacetates by a lithium naphthalenide induced reductive selenenylation process
Ko, Yen-Chun,Zhu, Jia-Liang
, p. 3659 - 3665 (2008/09/19)
An array of α,α-dialkyl-α-(phenylselanyl)acetates has been synthesized very efficiently from readily available α,α- dialkyl-α-cyanoacetates, by use of lithium naphthalenide induced reductive α-selenenylation as a key operation. Moreover, the selanyl esters thus generated in situ could be converted further, in a one-pot treatment with hydrogen peroxide and acetic acid, into the corresponding α,β- unsaturated esters in moderate to high yields. The C=C bond formation was highly regio- and/or diastereoselective in some cases. Georg Thieme Verlag Stuttgart.
