3853-80-3

Usage

Uses

Used in Pharmaceutical Industry:
(+/-)-2-Acetoxypropionic acid is used as a precursor in the synthesis of various pharmaceuticals for its ability to be chemically modified and incorporated into drug molecules.
Used in Agrochemical Industry:
(+/-)-2-Acetoxypropionic acid is used as a starting material in the production of agrochemicals, such as pesticides and herbicides, due to its reactivity and potential for creating effective compounds.
Used in Organic Synthesis:
(+/-)-2-Acetoxypropionic acid is used as a reagent in organic synthesis for its versatility in forming esters and other chemical derivatives, contributing to the development of new compounds and materials.

InChI:InChI=1/C5H8O4/c1-3(5(7)8)9-4(2)6/h3H,1-2H3,(H,7,8)

Upstream product

• 79-33-4 L-Lactic acid 
• 75-36-5 acetyl chloride 
• 56-41-7 L-alanin 
• 64-19-7 acetic acid 
• 108-24-7 acetic anhydride 
• 7664-93-9 sulfuric acid 
• 867-56-1 sodium L-lactate 
• 10326-41-7 D-Lactic acid 
• 93-92-5 1-phenylethyl acetate 
• 16197-93-6 (S)-1-phenylethyl acetate 
• 151838-56-1 (S)-2-acetoxypropionic acid benzyl ester 
• 535-17-1 2-acetoxypropionic acid 

Downstream Products

• 36394-75-9 (S)-2-acetoxypropanoyl chloride 
• 33105-51-0 acetyl-L-lactate-N-methylamide 
• 120444-05-5 (?)-(2S)-acetoxypropionic acid tert-butyl ester 
• 215593-41-2 (2S)-N-(2-tert-butylphenyl)-2-acetoxypropionamide 
• 251967-40-5 C₂₆H₄₂O₅Si 
• 331251-79-7 (2'S)-acetoxy-propionic acid (1S)-[(2'S)-acetoxy-propionyloxy]-(5S)-tert-butoxy-(4aS)-methyl-9-oxo-decahydro-cyclohepta[c]pyran-(3S)-yl ester 
• 116387-82-7 (S)-2-Acetoxy-propionic acid 4-methyl-2-thioxo-thiazol-3-yl ester 

Relevant academic research and scientific papers

Synthesis, pharmacological evaluation and molecular docking of novel R-/S-2-(2-hydroxypropanamido)-5-trifluoromethyl benzoic acid as dual anti-inflammatory anti-platelet aggregation agents

R-/S-2-(2-hydroxypropanamido) benzoic acid (R-/S-HPABA), marine-derived anti-inflammatory antiplatelet drugs, were initially synthesised in our group. However, preliminary research showed that R-/S-HPABA were eliminated rapidly because of extensive hydroxylation metabolism of phenyl ring in vivo. In order to reduce significant hydroxylation metabolism to improve pharmacological activity and bioavailability, trifluoromethyl group was incorporated into R-/S-HPABA to synthesise R-/S-2-(2-hydroxypropanamido)-5-trifluoromethyl benzoic acid (R-/S-HFBA), respectively. The purposes of this study were to report the synthesis of R-/S-HFBA and compare the anti-inflammatory antiplatelet effect and pharmacokinetic properties of R-/S-HFBA with those of R-/S-HPABA. Carrageenan-induced rat paw edema assay was used for the evaluation of the anti-inflammatory activity. R-/S-HFBA showed better results in inhibiting edema and were able to prolong the anti-inflammatory effect after carrageenan injection. The antiplatelet aggregation activity of R-/S-HFBA and R-/S-HPABA was studied on arachidonic acid-induced platelet aggregation of rabbit platelet-rich plasma. The aggregation inhibition rate of R-/S-HFBA was significantly (p max, larger AUC0-∞, and longer t1/2, which, as expected, are more metabolically stable.

NOVEL STING AGONISTS

The present invention provides compounds of Formula I′: wherein , W, X, Y, Z, Z1, Z2, R1, R2, R3, R4 and R5 are as defined herein, or a stereoisomer, tautomer, pharmaceutically acceptable salt, prodrug ester or solvate form thereof, wherein all of the variables are as defined herein. These compounds are effective at modulating the STING protein and thus can be used as medicaments for treating or preventing disorders affected by the agonism of STING.

Total Synthesis of (+)-Prunustatin A: Utility of Organotrifluoroborate-Mediated Prenylation and Shiina MNBA Esterification and Macrolactonization to Avoid a Competing Thorpe-Ingold Effect Accelerated Transesterification

A convergent total synthesis of (+)-prunustatin A is described through the assembly of two key fragments and a macrolactonization. Shiina MNBA couplings were used for the formation of each of the four ester bonds in the tetralactone ring, including the key macrocyclization which was essential to minimize competing Thorpe-Ingold accelerated transesterification. Other key steps included an organoboron-based prenylation using potassium prenyltrifluoroborate and a carbonyldiimidazole-mediated coupling to form the salicylamide.

Modifying oligoalanine conformation by replacement of amide to ester linkage

Oligo(lactic acid) is an ester-analogue of short oligoalanine sequence and adopts a rigid left-handed helical structure. In this study, oligo(lactic acid) was incorporated into oligoalanine sequences and their conformations were studied by vibrational circular dichroism and electronic circular dichroism spectroscopy. The results suggested that oligo(lactic acid) moiety in these sequences maintains a left-handed helix and increases the conformational propensity of the oligoalanine moiety to form a left-handed polyproline type II-like helix. The importance of the chirality of oligo(lactic acid) moiety for the oligoalanine conformation was also studied. The results obtained in this study should be useful in developing ester-containing oligopeptides that function better than normal peptides.

Preparation method and application of 2-lactoyl aminobenzoic acid

The invention relates to a new medicinal application of a chiral compound. The chiral compound is chemically named as R-/S-2-lactoyl aminobenzoic acid and has a structural formula as follows: formula (shown in the description). The compound is initially extracted and separated from secondary metabolite of microorganisms and can be obtained by virtue of a chemical synthetic method. An initial pharmacology experiment shows that the compound has good pain-easing and anti-inflammation activities and relatively low stimulation to gastrointestinal tracts. Recent researches prove that the compound has relatively good anti-platelet aggregation and anti-thrombus activities and is expected to be a novel non-steroidal anti-platelet aggregation and anti-thrombus drug.

Compounds And Compositions for the Treatment of Ocular Disorders

The disclosure describes prodrugs and derivatives of prostaglandins, carbonic anhydrase inhibitors, kinase inhibitors, beta-adrenergic receptor antagonists and other drugs, as well as controlled delivery formulations containing such prodrugs and derivatives, for the treatment of ocular disorders.

METHODS AND COMPOSITIONS FOR PREVENTING OPIOID ABUSE

Abuse-resistant opioid compounds, drug delivery systems, pharmaceutical compositions comprising an opioid covalently bound to a chemical moiety are provided. Methods of delivering an active ingredient to a subject and methods of preventing opioid abuse are also provided.

Total synthesis of actinophenanthroline A via double Doebner–Miller reaction

Total synthesis of actinophenanthroline A, a marine actinomycete within the family of Streptomycetaceae (strain CNQ-149) is reported. Both the racemic and enantiopure actinophenanthroline A have been synthesized with good overall yields. Highlight of the synthesis contains the classical and economical double Doebner–Miller reaction to access the 1,7-phenanthroline core followed by a modified EDCI coupling.

3-Aminoquinazolinones as chiral ligands in catalytic enantioselective diethylzinc and phenylacetylene addition to aldehydes

A series of readily known enantiomerically pure 3-aminoquinazolinones 1a-d were synthesised from easily accessible chiral pool α-hydroxy acids and α-amino acids in only four steps without any requirement of chromatography. These quinazolinones were examined as chiral ligands for catalytic enantioselective diethylzinc and phenylacetylene additions to aldehydes. For enantioselective alkylations, the effects of temperature, solvent, diethylzinc and ligand criteria were analysed, and the desired chiral alcohols were obtained in up to 86% ee. 3-Aminoquinazolinones 1a-d were also shown to be very useful ligands in enantioselective alkynylations of aldehydes. Based upon the optimised conditions, the corresponding propargylic alcohols were obtained in up to 94% ee.

CONTINUOUS PROCESS FOR THE PREPARATION OF (S)-2-ACETYLOXYPROPIONIC ACID CHLORIDE

The present invention relates to a continuous method for the preparation of (S)-2-acetyloxypropionic acid from an aqueous solution of lactic acid and acetic anhydride, in acetic acid. (S)-2-acetyloxypropionic acid is used for the preparation of (S)-2-acetyloxypropionic acid chloride, an essential intermediate compound for the preparation of Iopamidol and has to be industrially produced with high purity and suitable quality for producing Iopamidol according to the Pharmacopoeia requirements. The continuous process according to the invention, comprises therefore also the chlorination steps of (S)-2-acetyloxypropionic acid with thionyl chloride to give the corresponding (S)-2-acetyloxypropionic acid chloride which is further distilled to give the suitable purity characteristics for its use for the preparation of non-ionic iodinated contrast agents as Iopamidol.