123-66-0 Usage
Description
Ethyl caproate (also ethyl hexanoate) is naturally found in the fruits of Ananas sativus. It can be synthesized by the direct esterification of caproic acid with ethyl alcohol. It has strong, sweet-ethereal like pineapple odor, with nuances of banana and strawberry.
Ethyl caproate is approved by the FDA for food use (as a flavoring agent in desserts and beverages) without hazard to public health. Ethyl Caproate is used to synthesize novel EP2/EP4 dual agonist of γ-lactam prostaglandin E1 analogs. It is also used as a chemical reagent in the synthesis of PPARα antagonists in the treatment of metabolic diseases.
References
[1] D. L. J. Opdyke (1974) Monographs on Fragrance Raw Materials
[2] https://www.trc-canada.com
Chemical Properties
Different sources of media describe the Chemical Properties of 123-66-0 differently. You can refer to the following data:
1. CLEAR COLOURLESS LIQUID
2. Ethyl Hexanoate is a colorless liquid
with a strong fruity odor, reminiscent of pineapples. It occurs in many fruits and
is used in small amounts for floral, fruity notes in perfume compositions and in
larger quantities in fruit flavors.
3. Ethyl hexanoate has a powerful, fruity odor with a pineapple–banana note. It has been also reported to have a winy odor.
Occurrence
Reported found in strawberry, rum, bourbon, cocoa, kiwi fruit, black currant, apple, orange and grapefruit
juice, guava, Vitis vinifera, pineapple, strawberry jam, clove bud, cheeses, cognac, whiskies, grape wines, passion fruit juice, mango,
fruit brandies, figs, corn oil, mountain papaya, pawpaw and mastic gum leaf oil.
Uses
Different sources of media describe the Uses of 123-66-0 differently. You can refer to the following data:
1. Ethyl Caproate is used in the synthesis of novel EP2/EP4 dual agonist of γ-lactam prostaglandin E1 analogs. Also used as a chemical reagent in the synthesis of PPARα antagonists in the treatment of metabolic diseases.
2. Ethyl hexanoate may be used as an analytical reference standard for the determination of the analyte in wine and beer samples by chromatography based techniques.
3. manufacture of artificial fruit flavors.
Definition
ChEBI: A fatty acid ethyl ester obtained by the formal condensation of hexanoic acid with ethanol.
Preparation
By esterification of caproic acid with ethyl alcohol in the presence of concentrated H2SO4 or HCl
Aroma threshold values
Detection: 0.3 to 5 ppb
Taste threshold values
Taste characteristics at 10 ppm: fruity and waxy with a tropical nuance.
Synthesis Reference(s)
Journal of the American Chemical Society, 90, p. 818, 1968 DOI: 10.1021/ja01005a064Synthetic Communications, 14, p. 77, 1984 DOI: 10.1080/00397918408060867Synthesis, p. 929, 1978 DOI: 10.1055/s-1978-24945
General Description
Ethyl hexanoate is one of the odorants contributing to the typical guava aroma. It also contributes to the fresh strawberry aroma.
Safety Profile
A skin irritant.
Flammable liquid when exposed to heat or
flame; can react with oxidzing materials.
When heated to decomposition it emits
acrid smoke and irritating fumes. To fight
fire, use CO2, foam, dry chemical. See also
ESTERS.
Carcinogenicity
Not listed by ACGIH, California
Proposition 65, IARC, NTP, or OSHA.
Metabolism
Aliphatic esters, including ethyl caproate, are thought to be readily hydrolysed to the corresponding alcohol and acid, which are then further metabolized (Fassett, 1963). Ethyl caproate administered orally to rats produced a uniform ketonuria and it was considered probable that caproic acid was broken down chiefly by ?-oxidation (Deuel, Hallman, Butts & Murray, 1936). When 2 g ethyl caproate dissolved in aqueous ethanol was fed directly into the rumen of a cow, 0.003°/ was transferred to the milk, reaching a maximum level of 60 /fg/litre after 2-4 hr (Honkanen, Karvonen & Virtanen, 1964). The energy from ethyl caproate was 52% available when the ester was fed to four chicks at a level of 5% in the diet (Yoshida et al. 1970).
Check Digit Verification of cas no
The CAS Registry Mumber 123-66-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 3 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 123-66:
(5*1)+(4*2)+(3*3)+(2*6)+(1*6)=40
40 % 10 = 0
So 123-66-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H16O2/c1-3-5-6-7-8(9)10-4-2/h3-7H2,1-2H3
123-66-0Relevant articles and documents
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Adkins,Folkers,Kinsey
, p. 2714 (1931)
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Kinetic model for the esterification of ethyl caproate for reaction optimization
De Barros, Dragana P.C.,Pinto, Fatima,Fonseca, Luis P.,Cabral, Joaquim M.S.,Lemos
, p. 16 - 22 (2014)
The present work aims to achieve additional insight on a mechanism describing the fundamental steps involved in the esterification reactions catalyzed by cutinase. The synthesis of ethyl caproate has been used as a model system to obtain a suitable kinetic model to estimate the activation energies involved in the various steps of the reaction pathway. Kinetic measurements have been made for the enzymatic esterification of caproic acid with ethyl alcohol catalyzed by recombinant Fusarium solani pisi cutinase expressed in Saccharomyces cerevisiae SU50. Different temperature conditions, from 25 to 50 C, were tested for two different alcohol/acid molar ratios (R = 1 and R = 2). The third ordered Ping Pong Bi Bi mechanism with alcohol inhibition was shown to be able to describe the experimental results. The model shows that the productivity decreases as the reaction temperature increases.
Fully recyclable Br?nsted acid catalyst systems
Watson, Christopher B.,Kuechle, Adrianna,Bergbreiter, David E.
, p. 1266 - 1273 (2021/02/26)
Homogeneous and heterogeneous sulfonic acid catalysts are some of the most common catalysts used in organic chemistry. This work explores an alternative scheme using a fully recyclable polymeric solvent (a poly-α-olefin (PAO)) and soluble PAO-anchored polyisobutylene (PIB)-bound sulfonic acid catalysts. This PAO solvent is nonvolatile and helps to exclude water by its nonpolar nature which in turn drives reactions without the need for distillation of water, avoiding the need for excess reagents. This highly nonpolar solvent system uses polyisobutylene (PIB) bound sulfonic acid catalysts that are phase-anchored in solvents like PAO. The effectivenes of these catalysts was demonstrated by their use in esterifications, acetalizations, and multicomponent condensations. These catalysts and the PAO solvent phase show excellent recyclability in schemes where products are efficiently separated. For example, this non-volatile polymeric solvent and the PIB-bound catalyst can be recycled quantitatively when volatile products are separated and purified by distillation. In other cases, product purification can be effected by product self-separation or by extraction.
MOFs based on 1D structural sub-domains with Br?nsted acid and redox active sites as effective bi-functional catalysts
Díaz, Urbano,Moreno, José María,Velty, Alexandra
, p. 3572 - 3585 (2020/06/25)
A novel family of lamellar MOF-type materials, which contain Br?nsted acid sites together with redox active centers, based on assembled 1D organic-inorganic nanoribbons were obtained through direct solvothermal synthesis routes, using specific monotopic benzylcarboxylate spacers with thiol substituents in thepara-position like structural modulator compounds and effective post-synthesis oxidized treatments to generate accessible sulfonic groups. Low-dimensional aluminum metal-organic materials, containing free sulfonic pendant groups (Al-ITQ-SO3H), were successfully tested in several acid reactions, such as acetalization, esterification and ring opening of epoxides with a significant impact on fine chemistry processes. The direct introduction of stabilized Pd nanoparticles, cohabitating with pendant sulfonic groups, allowed the preparation of active bi-functional MOF-type hybrid materials (Al-ITQ-SO3H/Pd) capable of carrying out one-pot two-step oxidation-acetalization reactions, exhibiting high yield and high activity during consecutive catalytic cycles.
Selective hydrogenation of α,β-unsaturated carbonyl compounds on silica-supported copper nanoparticles
Mendes-Burak, Jorge,Ghaffari, Behnaz,Copéret, Christophe
supporting information, p. 179 - 181 (2019/01/04)
Silica-supported copper nanoparticles prepared via surface organometallic chemistry are highly efficient for the selective hydrogenation of various α,β-unsaturated carbonyl compounds yielding the corresponding saturated esters, ketones, and aldehydes in the absence of additives. High conversions and selectivities (>99%) are obtained for most substrates upon hydrogenation at 100-150 °C and under 25 bar of H2.
