209860-88-8

Basic information

• Product Name: 9ALPHA,11ALPHA-DIHYDROXY-15,15-DIFLUORO-16-PHENOXY-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID
• Synonyms: 9ALPHA,11ALPHA-DIHYDROXY-15,15-DIFLUORO-16-PHENOXY-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID;AFP-172;TAFLUPROST (FREE ACID);tafluprost acid;7-[2-(3,3-difluoro-4-phenoxybut-1-enyl)-3,5-dihydroxycyclopentyl]hept-5-enoic acid;9ALPHA,11ALPHA-DIHYDROXY-15,15-DIFLUORO-16-PHENOXY-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID
• CAS NO: 209860-88-8
• Molecular Formula: C₂₂H₂₈F₂O₅
• Molecular Weight: 410.45
• Mol File: 209860-88-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 575.9±50.0 °C(Predicted)
• Appearance: /
• Density: 1.271±0.06 g/cm3(Predicted)
• PKA: 4.76±0.10(Predicted)
• CAS DataBase Reference: 9ALPHA,11ALPHA-DIHYDROXY-15,15-DIFLUORO-16-PHENOXY-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 9ALPHA,11ALPHA-DIHYDROXY-15,15-DIFLUORO-16-PHENOXY-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID(209860-88-8)
• EPA Substance Registry System: 9ALPHA,11ALPHA-DIHYDROXY-15,15-DIFLUORO-16-PHENOXY-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID(209860-88-8)

Safety Data

• Hazardous Substances Data: 209860-88-8(Hazardous Substances Data)

Usage

Description

9ALPHA,11ALPHA-DIHYDROXY-15,15-DIFLUORO-16-PHENOXY-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID, also known as Tafluprost Acid, is a derivative of Tafluprost (T004820). It is a novel prostanoid characterized by its unique chemical structure, which includes dihydroxy, difluoro, and phenoxy functional groups. This molecule is specifically designed for its application in the medical field, particularly in the treatment of glaucoma.

Uses

Used in Ophthalmology:
9ALPHA,11ALPHA-DIHYDROXY-15,15-DIFLUORO-16-PHENOXY-17,18,19,20-TETRANOR-PROSTA-5Z,13E-DIEN-1-OIC ACID is used as a therapeutic agent for the treatment of glaucoma. It functions by reducing intraocular pressure, which is a primary risk factor for the development and progression of glaucoma. The unique chemical structure of Tafluprost Acid allows it to be effective in managing this condition, making it a valuable asset in the field of ophthalmology.
Additionally, as the first prostanoid to be released in a preservative-free formula, Tafluprost Acid offers a safer alternative for patients who may be sensitive or allergic to preservatives commonly found in eye drop formulations. This preservative-free aspect enhances patient compliance and reduces the risk of adverse reactions, further solidifying its importance in the treatment of glaucoma.

Upstream product

• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 209861-01-8 (3aR,4R,5R,6aS)-4-((E)-3,3-difluoro-4-phenoxybut-1-en-1-yl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one 
• 163074-98-4 [(3aR,4R,5R,6aS)-hexahydro-2-oxo-5-(phenylmethoxy)-2H-cyclopenta[b]furan-4-carboxaldehyde] 
• 81190-06-9 [(3aR,4S,5R,6aS)-hexahydro-4-(hydroxymethyl)-5-(phenylmethoxy)-2H-cyclopenta[b]furan-2-one] 
• 209861-00-7 (3aR,4R,5R,6aS)-4-((E)-3,3-difluoro-4-phenoxybutan-1-en-1-yl)-hexahydro-2-oxo-2H-cyclopenta[b]furan-5-yl benzoate 
• 51638-91-6 (3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate 
• 40665-68-7 dimethyl (3-phenoxy-2-oxopropyl)phosphonate 
• 209861-02-9 (3aR,4R,5R,6aS)-4-((E)-3,3-difluoro-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2,5-diol 
• 29782-85-2 rac-(trans)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol 
• 1487-05-4 rac-(trans)-3,3-dimethyltetrahydro-5H-oxireno[2',3':3,4]cyclopenta[1,2-d][1,3]dioxole 
• 5623-52-9 rac-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxole 
• 7129-41-1 6-oxabicyclo<3.1.0>hex-2-ene 

Downstream Products

• 1185851-52-8 (5Z)-N-ethyl-7-{(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-(phnoxy)but-1-enyl]-3,5-dihydroxycyclopentyl}hept-5-enamide 
• 1449413-13-1 C₂₂H₂₈F₂O₅*C₁₂H₂₃N 
• 209860-87-7 tafluprost 

Relevant articles and documents

Method for purifying tafluprost

The purpose of the present invention is to provide a simple and efficient method for purifying tafluprost that can be scaled up in proportion. The present invention relates to the method for purifying tafluprost, which comprises a step for purifying a crude product of tafluprost by silica gel column chromatography and collecting a component containing tafluprost by HPLC analysis. In addition, the present invention also relates to a method for producing tafluprost, which comprises the aforementioned method for purifying tafluprost.

An Asymmetric Suzuki-Miyaura Approach to Prostaglandins: Synthesis of Tafluprost

We report the catalytic asymmetric synthesis of Tafluprost (1), a prostaglandin analogue. This synthesis demonstrates a new approach to prostaglandins involving symmetrization and desymmetrization of a racemic precursor to control the absolute and relative stereochemistry of the cyclopentyl core. Key steps include a diastereo- and enantioselective Rh-catalyzed Suzuki-Miyaura reaction of a racemic bicyclic allyl chloride and an alkenyl boronic acid and a regio- and diastereoselective Pd-catalyzed Tsuji-Trost reaction with an enolate surrogate.

Processes for the preparation of isomer free prostaglandins

Novel processes for the preparation of a compound of Formula I-2 substantially free of the 5,6-trans isomer: wherein R2, R3 and R4 are as defined in the specification are provided. Novel intermediates for the preparations of isomer free Prostaglandins and derivatives thereof are also provided.