1540-38-1

Usage

Uses

Used in Food Industry:
3-(1-methylethyl)pentane-2,4-dione is used as a flavoring agent for its buttery or creamy flavor, enhancing the taste of various food products.
Used in Beverage Industry:
Diacetyl is used as a natural byproduct of fermentation, contributing to the unique flavor profiles of certain alcoholic beverages.
However, due to its potential health risks, the use of 3-(1-methylethyl)pentane-2,4-dione as a flavoring agent has been heavily regulated in many countries to ensure consumer safety and minimize the risk of respiratory issues associated with its inhalation.

InChI:InChI=1/C8H14O2/c1-5(2)8(6(3)9)7(4)10/h5,8H,1-4H3

Upstream product

• 108-24-7 acetic anhydride 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 108-10-1 4-methyl-2-pentanone 
• 5185-89-7 (3-acetyl-2-methyl-4-oxo-pentyl)-chloro-mercury 
• 7637-07-2 boron trifluoride 
• 1541-03-3 cis-CH₃COOC(CH₃)CHCH(CH₃)2 
• 75-26-3 isopropyl bromide 
• 123-54-6 acetylacetone 
• 187737-37-7 propene 
• 75-30-9 2-iodo-propane 
• 917-64-6 methyl magnesium iodide 
• 15181-39-2 3-ethylidene-pentane-2,4-dione 
• 15435-71-9 sodium acetylacetonate 

Downstream Products

• 38664-17-4 3-(4-acetyl-5-methyl-1H-pyrrol-3-yl)propanoic acid 
• 98885-97-3 (1E,6E)-1,7-Bis-(4-hydroxy-3-methoxy-phenyl)-4-isopropyl-hepta-1,6-diene-3,5-dione 
• 98886-05-6 (1E,6E)-1,7-Bis-(3,4-dimethoxy-phenyl)-4-isopropyl-hepta-1,6-diene-3,5-dione 

Relevant academic research and scientific papers

Chemoenzymatic Dynamic Kinetic Asymmetric Transformations of β-Hydroxyketones

Herein we report on the development and application of chemoenzymatic Dynamic Kinetic Asymmetric Transformation (DYKAT) of α-substituted β-hydroxyketones (β-HKs), using Candida antartica lipase B (CALB) as transesterification catalyst and a ruthenium complex as epimerization catalyst. An operationally simple protocol allows for an efficient preparation of highly enantiomerically enriched α-substituted β-oxoacetates. The products were obtained in yields up to 95 % with good diastereomeric ratios.

Catalytic hydroalkylation of olefins by stabilized carbon nucleophiles promoted by dicationic platinum(II) and palladium(II) complexes

The coordinated olefin in dicationic platinum(II) and palladium(II) complexes [M(PNP)(olefin)](SbF6)2 (M = Pt, Pd; PNP = 2,6-bis(diphenylphosphinomethyl)pyridine; olefin = ethylene, propylene) reacts with β-dicarbonyl compounds (pentane-2,4-dione and methyl-3-oxobutanoate). If the proton released after the nucleophilic attack is trapped by a base, stable σ-alkyl derivatives [(PNP)M-CH2-CH(R)CH(Ac)COR′] SbF6 (R = H, Me; R′ = Me, OMe) are formed; otherwise the M-C σ-bond can be cleaved by the proton, in the rate-determining step of a catalytic cycle that leads to the alkylated dicarbonyl compound. The β-diketone is intrinsically more reactive than the β-ketoester, but in the catalytic reaction of the former an inhibition effect is observed in the case of the platinum catalyst.

Cerium-catalyzed α-hydroxylation reactions of α-cyclopropyl β-dicarbonyl compounds with molecular oxygen

Three α-cyclopropyl β-dicarbonyl compounds have been used as probes for α-radicals as electrophilic reaction intermediates in a cerium-catalyzed α-hydroxylation reaction with molecular oxygen. Since the cyclopropyl group did not ring-open to products with a butenyl moiety, but was retained in the products, a localized unpaired electron at the α position can be excluded during the course of the reaction. The α-cyclopropyl- substituted substrates were prepared by aldol or Claisen reactions. Other substrates with α-methyl, α-isopropyl, and α-tert-butyl substituents were prepared and converted under the α-hydroxylation conditions in order to estimate steric influences on the yield of the reaction. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Use of the Nonionic Superbase P(MeNCH2CH2)3N in the Selective Monoalkylation of Active-Methylene Compounds

The symmetric active-methylene compounds CH2(CO2Et)2 and CH2[C(O)Me]2 are selectively monoalkylated in the presence of 1.1 equiv of a variety of alkyl halides and 1 equiv of the nonionic Superbase P(MeNCH2CH2)2N in 85-98% yields in 30 min at room temperature. The unsymmetrical active-methylene compound EtO2CCH2C(O)Me is selectively monoalkylated under the same conditions, except for the temperature, which is 0 °C, in 59-88% yields. The observation of selective C- rather than O-alkylation is rationalized in terms of the formation of an enolate whose negatively charged oxygen is sterically protected by a nearby HP(MeNCH2CH2)2N+ counterion in a tight ion pair.

Synthesis of Naturally Occuring Curcuminoids and Related Compounds

Six known naturally occuring curcuminoids like curcumin, and 31 other analogs (Scheme 1) have been synthesized.Among them, 25 curcuminoids were prepared by condensing different substituted 2,4-pentanediones and benzaldehydes.The boron complex 12 has been used to avoid Knoevenagel condensation at C-3 of 2,4-pentanedione.Some curcuminoids containing hydroxy groups in the aromatic moiety have been acylated.Alkylation of the tetrabutylammonium salt of 5-hydroxy-1,7-diphenyl-1,4,6-heptatrien-3-one (1a) by benzyl bromide gave only C-alkylated 4-benzyl-1,7-diphenyl-1,6-heptadiene-3,5-dione (1d*).The 13C NMR data, the UV absorptions, and the tautomerism of the curcuminoids are discussed.