4440-92-0

Usage

Uses

Used in Food Industry:
1,4-Butanedione is used as a flavoring agent for its ability to impart a rich, creamy taste to food products such as butter, cheese, and caramel. Its natural presence in some foods and its synthetic production make it a popular choice for enhancing the flavor of various food items.
Used in Flavor Manufacturing Industry:
In the flavor manufacturing industry, 1,4-butanedione is used as a key ingredient in creating artificial flavors that mimic the taste of dairy products. Its strong buttery odor and taste make it an essential component in the development of flavor compounds used in a wide range of food products.
However, due to the potential health risks associated with inhalation of diacetyl, the industry is taking steps to reduce or eliminate its use. This includes exploring alternative flavoring agents and implementing safety measures to protect workers from long-term exposure to the chemical.

Upstream product

• 2859-78-1 4-Bromoveratrole 
• 594-19-4 tert.-butyl lithium 
• 107-02-8 acrolein 
• 1835-04-7 ethyl 3,4-dimethoxyphenyl ketone 
• 91-16-7 1,2-dimethoxybenzene 
• 1835-05-8 2-bromo-1-(3,4-dimethoxyphenyl)propan-1-one 
• 4650-71-9 SK 31597 
• 74-88-4 methyl iodide 
• 93-07-2 Veratric acid 
• 4687-37-0 ethyl 3,4-dimethoxybenzoylacetate 
• 854679-72-4 ethyl 3-(3,4-dimethoxyphenyl)-2-methyl-3-oxopropanoate 
• 3943-77-9 ethyl veratrate 

Downstream Products

• 24150-24-1 terameprocol 
• 528-63-2 all-cis-3,4-dimethyl-2,5-bis(3,4-dimethoxyphenyl)tetrahydrofuran 
• 4676-33-9 3,4-dimethyl-2,5-bis(3,4-dimethoxyphenyl)furan 
• 528-63-2 (2R*,3R*,4R*,5S*)-2,5-bis(3,4-dimethoxyphenyl)-3,4-dimethyltetrahydrofuran 
• 521-54-0 (±)-galbulin 
• 528-63-2 (2R*,3R*,4R*,5R*)-2,5-bis(3,4-dimethoxyphenyl)-3,4-dimethyltetrahydrofuran 
• 5701-82-6 2,3-bis[(3,4-dimethoxyphenyl)methyl]butane 
• 5701-82-6 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane 
• 116588-90-0 3,6-Bis-(3,4-dimethoxy-phenyl)-1,4,5-trimethyl-1,4-dihydro-pyridazine 
• 116588-92-2 (+/-)-2,3-bis(3,4-dimethoxybenzoyl)butane-1-one-4-phenylhydrazone 
• 116588-91-1 3,6-Bis-(3,4-dimethoxy-phenyl)-4,5-dimethyl-1-phenyl-1,4-dihydro-pyridazine 
• 116588-89-7 3,6-Bis-(3,4-dimethoxy-phenyl)-4,5-dimethyl-4,5-dihydro-pyridazine 
• 103239-13-0 1,4-bis-(3,4-dimethoxy-phenyl)-2,3-dimethyl-butane-1,4-diol 

Relevant academic research and scientific papers

A macrocycle directed total synthesis of di-: O -methylendiandrin A

The total synthesis of the lignan-based cyclobutane di-O-methylendiandrin A has been achieved using diastereoselective, vicinal alkylation and transannular McMurry reactions of a macrocyclic 1,4-diketone as key transformations for establishing relative stereochemistry and furnishing the strained 4-membered ring of the natural product. This journal is

Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps

A very short three-step approach to trans,trans,trans-2,5-diaryl-3,4-dimethyltetrahydrofuran lignans is reported. The carbon skeleton is assembled in a single step based on an unprecedented tandem reaction consisting of 1,2-addition of aryllithium reagents to α,β-unsaturated aldehydes, ruthenium-catalyzed redox isomerization of the resulting alkoxides to enolates and their dimerization triggered by single electron oxidation. The resulting 2,3-dialkyl-1,4-diketones form with moderate to good d/l-diastereoselectivity and are transformed to the target tetrahydrofuran lignans by reduction and diastereoselective cycloetherification.

Synthesis of nordihydroguaiaretic acid derivatives and their bioactivities on S. pombe and K562 cell lines

Nordihydroguaiaretic acid (NDGA) and its synthetic analogues are potentially useful in treating diseases related to cancers, diabetes, viral and bacterial infections, and inflammation. In this paper, we report the optimal synthetic methods and the bioactivity study of terameprocol 2, NDGA derivative 3, and its cyclized analogue 4. The IC50 of these three compounds 2, 3 and 4 on the growth metabolism of Schizosacchromyces pombe and K562 cell lines were determined by microcalorimetry. The preliminary results showed that the compounds 2, 3 and 4 possessed good inhibition activities on S. pombe and K562 cell lines, and exhibited bidirectional biological effect and Hormesis effect. In particular, terameprocol 2 was found to possess the most potent inhibitory effect on K562 cell lines.

SCALABLE SYNTHETIC PROCESS FOR MAKING TERAMEPROCOL

A manufacturing process for making terameprocol (1) which includes the following reaction scheme, wherein a first general reaction is the formation of a furan intermediate (39) and a second general reaction is the ring-reduction and ring-opening of the furan intermediate (39) to form the terameprocol (1)

Cyclization of Diketones to Pyridazine and Furan Derivatives

Condensation of (+/-)-2,3-bis(3,4-dimethoxybenzoyl)butane-1,4-dione 1 with different hydrazine bases afforded the corresponding pyridazines 2 and 3.Refluxing the diketone 1 with methanolic hydrogen chloride yielded the corresponding 3,4-dimethylfuran derivative 5.Reaction of acetonylacetone 6 with p-sulfamylphenylhydrazine afforded the corresponding 3,6-dimethyl-1H-pyridazine derivative 7.Reaction of 7 with the appropriate isocyanate and isothiocyanate yielded the corresponding benzenesulfonylurea 8 and thiourea 9 derivatives respectively.The structures of the compounds synthesized were affirmed by microanalyses and spectral studies.