6034-46-4

Basic information

• Product Name: (S)-(-)-2-ACETOXYPROPIONIC ACID
• Synonyms: (-)-O-ACETYL-L-LACTIC ACID;(S)-A-2-ACETOXYPROPIONIC ACID;(S)-ACETYLLACTIC ACID;(S)-(-)-2-ACETOXYPROPIONIC ACID;(S)-ALPHA-ACETOXYPROPIONIC ACID;(-)-O-ACETYL-L-LACTIC AICD ;Propanoic acid, 2-(acetyloxy)-, (2S)-;(-)-2-O-Acetyl-L-lactic acid
• CAS NO: 6034-46-4
• Molecular Formula: C₅H₈O₄
• Molecular Weight: 132.11
• Product Categories: Carboxylic Acids (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry
• Mol File: 6034-46-4.mol
• Article Data: 35

Chemical Properties

• Boiling Point: 115-117 °C2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.162 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0298mmHg at 25°C
• Refractive Index: n20/D 1.422(lit.)
• Storage Temp.: 0-6°C
• PKA: 2.74±0.10(Predicted)
• CAS DataBase Reference: (S)-(-)-2-ACETOXYPROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-2-ACETOXYPROPIONIC ACID(6034-46-4)
• EPA Substance Registry System: (S)-(-)-2-ACETOXYPROPIONIC ACID(6034-46-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22
• Safety Statements: 26-27-28-36/39
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 6034-46-4(Hazardous Substances Data)

Usage

General Description

(S)-(-)-2-acetoxypropionic acid, also known as (S)-(-)-2-acetoxypropionic acid, is a chemical compound with the molecular formula C5H8O4. It is a chiral compound, meaning it has two enantiomers, (R)-2-acetoxypropionic acid and (S)-2-acetoxypropionic acid. (S)-(-)-2-ACETOXYPROPIONIC ACID is commonly used as an intermediate in the synthesis of pharmaceuticals and other organic compounds. It is also used as a chiral building block in the production of chiral chemicals. Additionally, it can be used as a resolving agent in the separation of racemic mixtures of organic compounds. The (S)-(-)-2-acetoxypropionic acid is widely utilized in the pharmaceutical and chemical industries due to its versatile applications.

InChI:InChI=1/C5H8O4/c1-3(5(7)8)9-4(2)6/h3H,1-2H3,(H,7,8)/t3-/m0/s1

Upstream product

• 79-33-4 L-Lactic acid 
• 7664-93-9 sulfuric acid 
• 867-56-1 sodium L-lactate 
• 64-19-7 acetic acid 
• 75-36-5 acetyl chloride 
• 10326-41-7 D-Lactic acid 
• 108-24-7 acetic anhydride 
• 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 
• 56-41-7 L-alanin 

Downstream Products

• 120448-63-7 acetyl-lactyl proline 
• 120448-66-0 acetyl-lactyl-prolyl-<(N-methyl)-D-leucyl>-threonine methyl ester 
• 36394-75-9 L-α-Acetoxypropionyl chloride 
• 126430-22-6 (S)-(-)-2-acetoxypropanoyl bromide 
• 143653-85-4 (S)-4-Acetoxy-2-methyl-3-oxo-pentanoic acid ethyl ester 
• 90687-80-2 (S)-2-Acetoxy-N-<(R)-α-methylbenzyl>propionamide 
• 90687-81-3 (S)-2-Acetoxy-N-<(S)-α-methylbenzyl>propionamide 
• 120444-05-5 (?)-(2S)-acetoxypropionic acid tert-butyl ester 
• 104293-36-9 2-<(1-Acetoxy)ethyl>-4-methylquinoline 
• 13650-70-9 (+)-tert-butyl D-lactate 
• 33105-51-0 acetyl-L-lactate-N-methylamide 

Relevant articles and documents

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.

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.

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.