144542-44-9

Basic information

• Product Name: (S)-4-(Hydroxymethyl)oxazolidin-2-one
• Synonyms: (S)-4-(Hydroxymethyl)oxazolidin-2-one;(4S)-4-(Hydroxymethyl)-2-oxazolidinone
• CAS NO: 144542-44-9
• Molecular Formula: C₄H₇NO₃
• Molecular Weight: 117.10328
• Mol File: 144542-44-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 430.6±14.0 °C(Predicted)
• Appearance: /
• Density: 1.288±0.06 g/cm3(Predicted)
• PKA: 12.11±0.40(Predicted)
• CAS DataBase Reference: (S)-4-(Hydroxymethyl)oxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-(Hydroxymethyl)oxazolidin-2-one(144542-44-9)
• EPA Substance Registry System: (S)-4-(Hydroxymethyl)oxazolidin-2-one(144542-44-9)

Safety Data

• Hazardous Substances Data: 144542-44-9(Hazardous Substances Data)

Usage

Description

(S)-4-(Hydroxymethyl)oxazolidin-2-one, commonly known as serine lactone, is a white crystalline chemical compound with the molecular formula C4H7NO3 and a melting point of approximately 120-122°C. It is a versatile intermediate utilized in the synthesis of pharmaceuticals and agrochemicals, as well as a valuable chiral building block in organic synthesis for creating various chiral compounds. Its potential antimicrobial and antifungal properties further contribute to its significance in different industries.

Uses

Used in Pharmaceutical and Agrochemical Industries:
(S)-4-(Hydroxymethyl)oxazolidin-2-one is used as an intermediate for the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and agricultural products.
Used as a Chiral Building Block in Organic Synthesis:
In the field of organic synthesis, (S)-4-(Hydroxymethyl)oxazolidin-2-one serves as a crucial chiral building block, enabling the preparation of a wide range of chiral compounds with specific stereochemistry.
Used in Antimicrobial and Antifungical Applications:
(S)-4-(Hydroxymethyl)oxazolidin-2-one has been investigated for its potential antimicrobial and antifungal properties, making it a promising candidate for applications in the medical and environmental sectors to combat microbial infections and fungal growth.

Upstream product

• 503001-47-6 (S)-(-)-4-acetoxymethyl-2-oxazolidinone 
• 15546-08-4 4-Hydroxymethyl oxazolidin-2-one 
• 144542-43-8 (R)-2-oxo-oxazolidine-4-carboxylic acid methyl ester 
• 96751-61-0 (S)-4-methoxycarbonyl-oxazolidin-2-one 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 155846-56-3 (2R)-2-amino-3-hydroxypropanoic acid hydrochloride 

Downstream Products

• 960205-66-7 C₂₂H₃₇NO₄Si 
• 1453082-82-0 (R)-4-(((tert-butyldiphenylsilanyl)oxy)methyl)oxazolidin-2-one 

Relevant articles and documents

Synthesis and evaluation of a potent, well-balanced EP2/EP3 dual agonist

A highly potent and well-balanced dual agonist for the EP2 and EP3 receptors is described. Optimization of the lead compound was accomplished in consideration of the relative agonist activity against each EP subtype receptor and the pharmacokinetic profile. As the result, 2-[(2-{(1R,2R)-2-[(1E,4S)-5-cyclopentyl-4-hydroxy-4-methyl-1-penten-1-yl]-5-oxocyclopentyl}eth-yl)thio]-1,3-thiazole-4-carboxylic acid (10) showed excellent potency (human EC50 EP2 = 1.1 nM, EP3 = 1.0 nM) with acceptable selectivity over the EP1 and EP4 subtypes (>2000-fold). Further fine-tuning of compound 10 led to identification of ONO-8055 as a clinical candidate. ONO-8055 was effective at an extremely low dose (0.01 mg/kg, po, bid) in rats, and dose-dependently improved voiding dysfunction in a monkey model of underactive bladder (UAB). ONO-8055 is expected to be a novel and highly promising drug for UAB.

COMPOUNDS AND METHODS FOR TREATING BACTERIAL INFECTIONS

Compounds of formula (I), pharmaceutically acceptable salts thereof, and uses of the compounds of formula (I) for treating bacterial infections are disclosed.

BLOOD FLOW PROMOTERS FOR CAUDA EQUINA TISSUES

It is intended to provide highly safe and efficacious blood flow promoters for cauda equina tissues. Among prostaglandin-like compounds having a weak hypotensive effect, compounds having an effect of promoting the blood flow in cauda equina tissues (excluding limaprost) are useful as highly safe blood flow promoters for cauda equina tissues and , therefore, are efficacious in preventing and/or treating lumbar pain, lower limb pain, lower limb palsy, intermittent claudication, vesicorectal failure, hypogonadism, etc. caused by cauda equina injuries.