83802-77-1

Basic information

• Product Name: retinoyl fluoride
• Synonyms: retinoyl fluoride
• CAS NO: 83802-77-1
• Molecular Formula: C₂₀H₂₇FO
• Molecular Weight: 0
• Mol File: 83802-77-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 414.5°C at 760 mmHg
• Flash Point: 157.5°C
• Appearance: /
• Density: 0.991g/cm³
• Vapor Pressure: 4.43E-07mmHg at 25°C
• Refractive Index: 1.529
• CAS DataBase Reference: retinoyl fluoride(CAS DataBase Reference)
• NIST Chemistry Reference: retinoyl fluoride(83802-77-1)
• EPA Substance Registry System: retinoyl fluoride(83802-77-1)

Safety Data

• Hazardous Substances Data: 83802-77-1(Hazardous Substances Data)

Usage

Uses

all-trans-Retinoyl Fluoride is an intermediate used in the synthesis of all-trans Retinoyl β-D-Glucuronide (R253500), which is a biliary metabolite of Vitamin A, occurs endogenously in human blood. RAG is biologically active in promoting the growth of vitamin A-deficient rats and the induction of differentiation of HL-60 and BA-HAN-1C cells, but less cytotoxic than Retinoic Acids.

InChI:InChI=1/C20H27FO/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3/b9-6+,12-11+,15-8-,16-14-

Upstream product

• 302-79-4 all-trans-retinoic-acid 

Downstream Products

• 205872-69-1 5,6-O-isopropylidene-2-O-methyl-3-O-retinoyl-L-ascorbic acid 
• 167095-80-9 3-O-retinoyl-L-ascorbic acid 
• 167095-79-6 5,6-O-isopropylidene-3-O-retinoyl-L-ascorbic acid 
• 153321-67-6 Retinoic Acid glucuronide 
• 68-26-8 RETINOL 
• 302-79-4 all-trans-retinoic-acid 
• 339-16-2 all-trans-methyl retinoate 

Relevant articles and documents

Synthesis of the 3-o-retinoyl-l-ascorbic acid and related compounds: Characterization and reducing activity against DPPH

Novel hybrid vitamin, 3-O-retinoyl-L-ascorbic acid (3a) was conveniently prepared by reaction of sodium L-ascorbate with retinoyl fluoride. The 3-O-acylated structure was confirmed by the comparison of spectral data of its methylated compound with those of 3-O-methyl-2-O-retinoyl-L-ascorbic acid (20) prepared from 5,6-O-isopropylidene-3-O-methyl-L-ascorbic acid. 3-O-Retinoyl-L-ascorbic acid (3a) showed a reducing activity against the stable radical, α,α-diphenyl-β-picrylhydrazyl (DPPH).

All E-10,20-methanoretinoylopsin, light-stable rhodopsin. Synthesis and spectroscopy of all E-10,20-methano- and all-E-retinoyl fluoride and their reaction with bovine opsin

In order to obtain a light-stable rhodopsin as a potential candidate for crystallization and structural X-ray analysis, we synthesized and characterized the novel all E-10,20-methanoretinoyl fluoride (2).This retinal analogue has a locked 11-cis configuration, preventing the light-induced 11-cis -> trans isomerization and binds to opsin by a stable peptide bond rather than a Schiff base. 2 reacted with (methylated) bovine opsin, forming a light- and thermo-stable pigment with λmax at 390 nm.Its opsin shift (2500 cm-1) is in the same order of magnitude as that in rhodopsin (2650 cm-1), suggesting that the mechanism for the red shift is not located in the direct vicinity of the chromophore-protein linkage.We also report the first synthesis and characterization of all-E-retinoyl fluoride (10), which failed to give a pigment on reaction with bovine opsin.

Inactivation of Bovine Opsin by all-trans-Retinoyl Fluoride

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