87950-39-8

Usage

Uses

Used in Organic Synthesis:
4-(3,4-DIACETOXYBENZAL)-2-METHYL-5-OXAZOLONE is used as a key intermediate in organic synthesis for the preparation of various complex organic molecules. Its unique structure allows it to participate in a range of reactions, such as condensation, acylation, and substitution, which are crucial for constructing diverse organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-(3,4-DIACETOXYBENZAL)-2-METHYL-5-OXAZOLONE is used as a building block for the synthesis of pharmaceutical compounds. Its reactivity and structural features make it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
4-(3,4-DIACETOXYBENZAL)-2-METHYL-5-OXAZOLONE is also utilized in chemical research as a model compound to study various reaction mechanisms and to develop new synthetic methodologies. Its unique properties provide researchers with opportunities to explore novel approaches to organic synthesis and to gain insights into the fundamental aspects of chemical reactions.
Used in Material Science:
In the field of material science, 4-(3,4-DIACETOXYBENZAL)-2-METHYL-5-OXAZOLONE can be employed as a precursor for the development of new materials with specific properties. Its ability to undergo various chemical transformations allows for the creation of materials with tailored characteristics for use in different applications, such as sensors, catalysts, or advanced materials for energy storage and conversion.

Upstream product

• 108-24-7 acetic anhydride 
• 543-24-8 N-acetylglycine 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 127-09-3 sodium acetate 
• 67727-64-4 3,4-diacetoxybenzaldehyde 

Downstream Products

• 23028-17-3 danshensu 
• 64521-33-1 2-acetylamino-3-(3,4-dihydroxyphenyl)-propenoic acid 
• 65329-03-5 2-(acetylamino)-3-[3,4-bis(acetyloxy)phenyl]-(2Z)-2-propenoic acid 
• 65329-03-5 α-acetylamino-β-(3,4-diacetoxyphenyl)acrylic acid 
• 4228-66-4 L-586462 
• 68307-79-9 (Z)-3-(3,4-dihydroxyphenyl)-2-hydroxyacrylic acid 

Relevant academic research and scientific papers

Mechanistically Guided One Pot Synthesis of Phosphine-Phosphite and Its Implication in Asymmetric Hydrogenation

Although hybrid bidentate ligands are known to yield highly enantioselective products in asymmetric hydrogenation (AH), synthesis of these ligands is an arduous process. Herein, a one pot, atom-economic synthesis of a hybrid phosphine-phosphite (L1) is reported. After understanding the reactivity difference between an O-nucleophile versus C-nucleophile, one pot synthesis of Senphos (L1) was achieved (72 %). When L1 was treated with [Rh], 31P NMR revealed bidentate coordination to Rh. Senphos, in the presence of rhodium, catalyzes the AH of Methyl-2-acetamido-3-phenylacrylate and discloses an unprecedented turn over frequency of 2289, along with excellent enantio-selectivity (92 %). The generality is demonstrated by hydrogenating an array of alkenes. The AH operates under mild conditions of 1–2 bar H2 pressure, at room temperature. The practical relevance of L1 is demonstrated by scaling-up the reaction to 1 g and by synthesizing DOPA, a drug widely employed for the treatment of Parkinson's disease. Computational insights indicate that the R isomer is preferred by 3.8 kcal/mol over the S isomer.

TRPV4 activity inhibitor

PROBLEM TO BE SOLVED: To provide a compound that inhibits TRPV4 activity and is useful for prevention or improvement of overactive bladder and irritable bowel syndrome or the like. SOLUTION: A TRPV4 activity inhibitor has a rosmarinic acid derivative selected from the formulae (Ia)-(Id) or a salt thereof as an active ingredient. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Deracemization and Stereoinversion of α-Amino Acids by l-Amino Acid Deaminase

Enantiomerically pure α-amino acids are compounds of primary interest for the fine chemical, pharmaceutical, and agrochemical sectors. Amino acid oxidases are used for resolving d,l-amino acids in biocatalysis. We recently demonstrated that l-amino acid deaminase from Proteus myxofaciens (PmaLAAD) shows peculiar features for biotechnological applications, such as a high production level as soluble protein in Escherichia coli and a stable binding with the flavin cofactor. Since l-amino acid deaminases are membrane-bound enzymes, previous applications were mainly based on the use of cell-based methods. Now, taking advantage of the broad substrate specificity of PmaLAAD, a number of natural and synthetic l-amino acids were fully converted by the purified enzyme into the corresponding α-keto acids: the fastest conversion was obtained for 4-nitrophenylalanine. Analogously, starting from racemic solutions, the full resolution (ee >99%) was also achieved. Notably, d,l-1-naphthylalanine was resolved either into the d- or the l-enantiomer by using PmaLAAD or the d-amino acid oxidase variant having a glycine at position 213, respectively, and was fully deracemized when the two enzymes were used jointly. Moreover, the complete stereoinversion of l-4-nitrophenylalanine was achieved using PmaLAAD and a small molar excess of borane tert-butylamine complex. Taken together, recombinant PmaLAAD represents an l-specific amino acid deaminase suitable for producing the pure enantiomers of several natural and synthetic amino acids or the corresponding keto acids, compounds of biotechnological or pharmaceutical relevance. (Figure presented.).

Danshensu method for an industrial synthesis of isopropyl ester

The invention relates to an industrial synthesis method of isopropyl tanshinol, which comprises the following step: in the presence of the second hydrochloric acid and a reducing agent Zn-Hg, beta-(3,4-dihydroxylphenyl)pyruvic acid reacts with isopropyl ester in a solvent to generate the isopropyl tanshinol, wherein the beta-(3,4-dihydroxylphenyl)pyruvic acid is obtained by hydrolyzing 2-methyl-4-(3,4-diacetoxylbenzal)oxazole in the first hydrochloric acid. In the method provided by the invention, esterification and modification reducing reaction are performed at the same time. The synthesis of an intermediate product tanshinol in a synthesis method is omitted, the process operation is simplified, and the production period is shortened. Moreover, since the beta-(3,4-dihydroxylphenyl)pyruvic acid is directly obtained by hydrolyzing 2-methyl-4-(3,4-diacetoxylbenzal)oxazole in the hydrochloric acid solution, the process operation is further simplified.

The industrialization to a method for synthesizing danshensu

The invention relates to an industrial synthesis method of bornyl tanshinol, which comprises the following step: in the presence of the second hydrochloric acid, a reducing agent Zn-Hg and a catalyst, beta-(3,4-dihydroxylphenyl)pyruvic acid reacts with borneol in a solvent to generate the bornyl tanshinol, wherein the beta-(3,4-dihydroxylphenyl)pyruvic acid is obtained by hydrolyzing 2-methyl-4-(3,4-diacetoxylbenzal)oxazole in the first hydrochloric acid. In the method provided by the invention, esterification and modification reducing reaction are performed at the same time. The synthesis of an intermediate product tanshinol in a synthesis method is omitted, the process operation is simplified, and the production period is shortened. Moreover, since the beta-(3,4-dihydroxylphenyl)pyruvic acid is directly obtained by hydrolyzing 2-methyl-4-(3,4-diacetoxylbenzal)oxazole in the hydrochloric acid solution, the process operation is further simplified.

New compounds having skin whitening, antioxidant and PPAR activity, and medical use thereof

PURPOSE: A novel compound with skin whitening, antioxidation, and PPAR activation effects, and a medical use thereof are provided to be used for a pharmaceutical composition or a cosmetic product. CONSTITUTION: A compound is denoted by chemical formula 1. A skin whitening composition contains the compound as an active ingredient. An antioxidative composition for preventing or treating oxidative diseases contains the compound of chemical formula 1 as an active ingredient. The oxidative diseases are selected among skin aging, pigmentation, wrinkling, psoriasis, or eczema. The composition prevents or treats diseases which are regulated by PPAR(peroxisome proliferator-activated receptor) activity. The PPAR includes PPAR alpha or PPAR gamma.

NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR

Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.

Green synthesis of β-(3,4-dihydroxyphenyl)lactic acid

A new method has been developed for the synthesis of β-(3,4- dihydroxyphenyl)lactic acid, an active ingredient for the treatment of myocardial ischemia. Pd/C catalysts were used in the key reduction reaction to replace the traditionally used toxic Zn/Hg catalysts. A significantly high product yield of 99.7 % was obtained under the optimal reaction conditions, through the use of orthogonal experimental design, when reaction temperature, catalyst (5 % Pd/C) amount and pressure were 60 °C, 20 wt % and 1.0 MPa, respectively.

SUBSTITUTED BETA-PHENYL-ALPHA-HYDROXY PROPANOIC ACID, SYNTHESIS METHOD AND USE THEREOF

The present invention relates to a compound of the formula (I), wherein R1, R2 and R3 are each independently selected from H, OH, F, Cl, Br, methoxy and ethoxy; or alternatively, R1 and R2 together form -OCH2O-, R3 is selected from H, OH, methoxy, ethoxy and halogens; R4 is OH or acyloxy; R5 is cycloalkoxyl, amino and substituted amino, and when R5 is selected from amino, at least one of R1, R2 and R3 is not H. The present invention further relates to a process for synthesizing a compound of the formula (I), and use of the compound of the formula (I) in the manufacture of a medicament for the prevention or treatment of cardiovascular or cerebrovascular diseases.

The first expedient entry to the human melanogen 2-S-cysteinyldopa exploiting the anomalous regioselectivity of 3,4-dihydroxycinnamic acid-thiol conjugation

The first convenient synthesis of 2-S-cysteinyl-3,4-dihydroxyphenylalanine (2-S-cysteinyldopa) in 30% overall yield is reported, which capitalizes on the anomalous regiochemistry of the oxidative coupling of 3,4-dihydroxycinnamic acid derivatives with thi