121010-58-0

Basic information

• Product Name: [(1R,2S,3S,4R,5S,6R)-3,4-dihydroxy-2,5,6-triphosphonooxy-cyclohexyl]oxyphosphonic acid
• Synonyms: [(1R,2S,3S,4R,5S,6R)-3,4-dihydroxy-2,5,6-triphosphonooxy-cyclohexyl]oxyphosphonic acid;1D-myo-Inositol 1,4,5,6-tetrakisphosphate;inositol-1,4,5,6-tetrakisphosphate;Myo-inositol, 1,4,5,6-tetrakis(dihydrogen phosphate);Myo-inositol-1,4,5,6-tetrakisphosphate
• CAS NO: 121010-58-0
• Molecular Formula: C₆H₁₆O₁₈P₄
• Molecular Weight: 500.08
• Product Categories: Carbohydrates & Derivatives;Inositols;Phosphorylating and Phosphitylating Agents;Carbohydrates & Derivatives, Inositols, Phosphorylating and Phosphitylating Agents
• Mol File: 121010-58-0.mol

Chemical Properties

• Boiling Point: 978.1°Cat760mmHg
• Flash Point: 545.3°C
• Appearance: /
• Density: 2.32g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.632
• CAS DataBase Reference: [(1R,2S,3S,4R,5S,6R)-3,4-dihydroxy-2,5,6-triphosphonooxy-cyclohexyl]oxyphosphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [(1R,2S,3S,4R,5S,6R)-3,4-dihydroxy-2,5,6-triphosphonooxy-cyclohexyl]oxyphosphonic acid(121010-58-0)
• EPA Substance Registry System: [(1R,2S,3S,4R,5S,6R)-3,4-dihydroxy-2,5,6-triphosphonooxy-cyclohexyl]oxyphosphonic acid(121010-58-0)

Safety Data

• Hazardous Substances Data: 121010-58-0(Hazardous Substances Data)

Usage

Uses

Used in Biological Research:
Ins(1,4,5,6)P4 is used as a substrate in biological research to study the function and specificity of human Ins(3,4,5,6)P4 1-kinase (hITPK1). Its unique stereochemistry allows researchers to investigate the role of stereochemistry factors in the enzyme's specificity.
Used in Drug Development:
Ins(1,4,5,6)P4 has potential applications in drug development, as it can be phosphorylated by inositol-phosphate-multikinase. This property can be exploited to develop new drugs targeting specific kinases and their substrates, leading to the discovery of novel therapeutic agents.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Ins(1,4,5,6)P4 can be used as a starting material for the synthesis of other biologically active compounds. Its unique structure and properties make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Diagnostics:
Ins(1,4,5,6)P4 can also be used in diagnostic applications, as its presence and levels in biological samples can provide valuable information about the activity of specific enzymes and metabolic pathways. This can help in the diagnosis and monitoring of various diseases and conditions.
Overall, [(1R,2S,3S,4R,5S,6R)-3,4-dihydroxy-2,5,6-triphosphonooxy-cyclohexyl]oxyphosphonic acid, or Ins(1,4,5,6)P4, is a versatile and important molecule with a wide range of applications in various fields, including biological research, drug development, pharmaceutical industry, and diagnostics. Its unique structure and properties make it a valuable tool for understanding and targeting specific biological processes and pathways.

InChI:InChI=1/C6H16O18P4/c7-1-2(8)4(22-26(12,13)14)6(24-28(18,19)20)5(23-27(15,16)17)3(1)21-25(9,10)11/h1-8H,(H2,9,10,11)(H2,12,13,14)(H2,15,16,17)(H2,18,19,20)/t1-,2+,3-,4-,5+,6+/m1/s1

Upstream product

• 57029-87-5 (±)-1,2-cyclohexylidene myo-inositol 
• 114488-20-9 myo-Inositol 1,5,6-trisphosphate 
• 181782-84-3 D-2,3-Di-O-butyryl-myo-inositol 
• 80582-74-7 (1S,2S,3S,4S)-anti-benzene dioxide 
• 163580-32-3 D-2,3-Di-O-butyryl-myo-inositol 1,4,5,6-tetrakisphosphate 
• 157542-48-8 D-2,3-O-cyclohexylidene-1,4,5,6-tetra-O-(bisbenzyloxyphosphoryl)-myo-inositol 

Downstream Products

• 114488-20-9 myo-Inositol 1,5,6-trisphosphate 
• 26326-86-3 Ins(1,2,3,4,5)P₅ 

Relevant articles and documents

Regulation of ins(3456)p4 signalling by a reversible kinase phosphatase and methods and compositions related thereto

Provided is a method of increasing 3,4,5,6-tetrakisphosphate by increasing the activity of inositol 1,3,4,5,6 pentakisphosphate 1-phosphatase, and a method of decreasing 3,4,5,6-tetrakisphosphate by decreasing the activity of inositol 1,3,4,5,6 pentakisph

Diastereoselective synthesis of D- and L-myo-inositol 3,4,5,6- tetrakisphosphates from D-glucose via dihydroxylation of (+)-conduritol B derivatives

Syntheses of D- and L-myo-inositol 3,4,5,6-tetrakisphosphates were achieved via diastereoselective 1,2-addition of vinylcopper reagent with the chiral aldehyde prepared from 1,2,5,6-diisopropylidene-D-glucose, ring-closing metathesis of 1,7-diene with Gru

A Definitive Synthesis of D-myo-Inositol 1,4,5,6-Tetrakisphosphate and Its Enantiomer D-myo-Inositol 3,4,5,6-Tetrakisphosphate from a Novel Butane-2,3-diacetal-Protected Inositol

New and rapid syntheses of the enantiomeric intracellular signalling molecules D-myo-inositol 1,4,5,6-tetrakisphosphate (1a) and D-myo-inositol 3,4,5,6-tetrakisphosphate (1b) are described. The synthetic strategy employs the novel butane-2,3-diacetal-prot

Divergent syntheses of all possible optically active regioisomers of myo-inositol tris- and tetrakisphosphates

Since the discovery of D-myo-inositol 1,4,5-trisphosphate, which plays a pivotal role as a second messenger in transmembrane signaling, the scope of the phosphoinositide-based signaling processes has been continually expanding. However, the clear understanding of the molecular signal transduction mechanisms including the functions of newly found IPn is still lacking. As a continuing effort to our previously reported syntheses of all possible 39 optically inactive regioisomers of myoinositol phosphates (IPn; n = 1-6), we synthesized all possible optically active regioisomers of myo-IP3 and myo-IP4 using chiral IBz3s and IBz2s, respectively. A series of procedures involving CRL-catalyzed enzymatic resolution of racemic 1,2:5,6-di-O-isopropylidene-myo-inositol and base-catalyzed benzoyl migration in tri- and dibenzoyl-isopropylidene-myo-inositol afforded eight enantiomeric pairs of IBz3 and six enantiomeric pairs of IBz2, respectively. Phosphorylation of these intermediates by the phosphitylation and oxidation procedure gave the target products.

Enzyme-assisted total synthesis of the optical antipodes D-myo-inositol 3,4,5-trisphosphate and D-myo-inositol 1,5,6-trisphosphate: Aspects of their structure-activity relationship to biologically active inositol phosphates

Unambiguous total syntheses of both optical antipodes of the enantiomeric pair D-myo-inositol 3,4,5-trisphosphate (Ins(3,4,5)P3) and D- myo-inositol 1,5,6-trisphosphate (Ins(1,5,6)P3) are described. The ring system characteristic of

Membrane-permeant analogues of the putative second messenger myo-inositol 3,4,5,6-tetrakisphosphate

For future investigations of the binding properties of D-myo-inositol 3,4,5,6- and 1,4,5,6-tetrakis-phosphate [D-Ins(3,4,5,6)P4 and D-Ins(1,4,5,6)P4, respectively] to their putative target proteins, a set of analogues with modificati

Lipase-catalyzed regio- and enantioselective esterification of rac-1,2-O-cyclohexylidene-myo-inositol

The hydroxyl group at C-5 in racemic 1,2-O-Cyclohexylidene-myo-inositol (rac-1) was regio- and enantioselectively acylated to give 5-O-acetyl- (2a)- or 5-O-butyryl-2,3-O-cyclohexylidene-myo-inositol (3a), respectively, by treatment of 1 with vinyl acetate

Synthesis of D-myo-inositol 3,4,5,6- and 1,4,5,6-tetrakisphosphate analogues and their membrane-permeant derivatives

A set of D-myo-inositol 3,4,5,6- and 1,4,5,6-tetrakisphosphates [D-Ins(3,4,5,6)P4 and D-Ins(1,4,5,6)P4, respectively] analogues with modifications of the hydroxy groups is synthesized and subsequently converted to the corresponding u