488-54-0

Basic information

• Product Name: neo-Inositol
• Synonyms: neo-Inositol
• CAS NO: 488-54-0
• Molecular Formula: C₆H₁₂O₆
• Molecular Weight: 180.16
• Mol File: 488-54-0.mol

Chemical Properties

• Boiling Point: 291.3°Cat760mmHg
• Flash Point: 143.4°C
• Appearance: /
• Density: 2.038g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.784
• CAS DataBase Reference: neo-Inositol(CAS DataBase Reference)
• NIST Chemistry Reference: neo-Inositol(488-54-0)
• EPA Substance Registry System: neo-Inositol(488-54-0)

Safety Data

• Hazardous Substances Data: 488-54-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4-,5-,6-

Upstream product

• 87-89-8 D-myo-inositol 
• 79391-04-1 O-α-D-galactopyranosyl-(1->2)-D-chiroinositol 
• 149820-68-8 1,2-O-isopropylidene-D-chiro-inositol 
• 488-66-4 (2R)-2r,3c,4t,5c,6t-pentahydroxy-cyclohexanone 
• 7732-18-5 water 
• 127666-06-2 (3aS,7aS)-4-chloro-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole 
• 18391-54-3 1D-O³,O⁴;O⁵,O⁶-diisopropyliden-1,2-anhydro-allo-inositol 
• 130669-73-7 (1S,2R,3R,4S,5R,6S)-2,3-dihydroxy-4,5-di-O-isopropylidene-7-oxabicyclo<4.1.0>heptane 
• 7664-93-9 sulfuric acid 
• 145107-29-5 (+)-Conduritol E epoxide 
• 64-17-5 ethanol 
• 608-80-0 benzenehexol 
• 342789-67-7 (E)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galacto-hex-5-enopyranoside 
• 86992-79-2 (1S,2S)-3-Chloro-cyclohexa-3,5-diene-1,2-diol 

Downstream Products

• 488-66-4 (2R)-2r,3c,4t,5c,6t-pentahydroxy-cyclohexanone 
• 4099-90-5 myo-inositol hexabenzoate 
• 2582-79-8 [(1R,2R,3S,4S,5S,6S)-cyclohexane-1,2,3,4,5,6-hexaylhexakis(oxy)]hexakis(trimethylsilane) 
• 83-86-3 neo-inositol 1,2,3,4,5,6-hexakisphosphate 
• 20097-40-9 hexa-O-acetyl-neo-inositol 
• 98136-19-7 2r,3t,5t,6c-tetrahydroxy-cyclohexane-1,4-dione 
• 849670-29-7 hexa-O-benzoyl-myo-inositol 
• 551-72-4 inositol 

Relevant articles and documents

A short, stereoselective synthesis of neo-inositol

A practical synthesis of neo-inositol is described in which the target is prepared on a multigram scale in six operations from bromobenzene. Copyright (C) 2000 Elsevier Science Ltd.

METHODS OF SYNTHESIS OF SCYLLITOL AND RELATED COMPOUNDS

Methods of synthesis of scyllitol diborate and related compounds are provided, including methods that are performed in all-aqueous solutions. Also provided are methods in which the reaction products are recycled to increase the efficiency of the process. The methods include the steps of conversion of a solution of inositol to scyllitol, conversion of scyllitol in the solution to scyllitol diborate, and isolation of the scyllitol diborate from the solution. The scyllitol diborate is reacted to form substantially pure scyllitol diborate, and the remaining solution is efficiently recycled to scyllitol diborate, then to additional substantially pure scyllitol. This scyllitol diborate recycling step can be applied to a variety of processes to improve the yield of scyllitol. The methods are highly efficient and result in large scale reaction products of high purity.

A short and efficient route from myo - To neo -inositol

An efficient route from myo- to neo-inositol is described. The key steps of the sequence are oxidation of the hydroxy group at C-5 to the corresponding ketone, followed by a highly (dr = 7.8:1) stereoselective reduction. The route includes nine steps with an overall yield of 51% and is therefore superior to all hitherto reported methods for the preparation of neo-inositol. Georg Thieme Verlag Stuttgart New York.

Stereoselective synthesis of myo-, neo-, L-chiro, D-chiro, allo-, scyllo-, and epi-inositol systems via conduritols prepared from p-benzoquinone

A practical route is described for the flexible preparation of a wide variety of inositol stereoisomers and their polyphosphates. The potential of this approach is demonstrated by the synthesis of myo-, L-chiro-, D-chiro-, epi-, scyllo-, allo-, and neo-inositol systems. Optically pure compounds in either enantiomeric form can be prepared from p-benzoquinone via enzymatic resolution of a derived conduritol B key intermediate. High-performance anion-exchange chromatography with pulsed amperometric detection permits inositol stereoisomers to be resolved and detected with high sensitivity. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Stereo- and regiospecificity of yeast phytases-chemical synthesis and enzymatic conversion of the substrate analogues neo- and L-chiro-inositol hexakisphosphate

Phytases are enzymes that catalyze the hydrolysis of phosphate esters in myo-inositol hexakisphosphate (phytic acid). The precise routes of enzymatic dephosphorylation by phytases of the yeast strains Saccharomyces cerevisiae and Pichia rhodanensis have been investigated up to the myo-inositol trisphosphate level, including the absolute configuration of the intermediates. Stereoselective assignment of the myo-inositol pentakisphosphates (D-myo-inositol 1,2,4,5,6-pentakisphosphate and D-myo-inositol 1,2,3,4,5-pentakisphosphate) generated was accomplished by a new method based on enantiospecific enzymatic conversion and HPLC analysis. Via conduritol B or E derivatives the total syntheses of two epimers of myo-inositol hexakisphosphate, neo-inositol hexakisphosphate and L-chiro-inositol hexakisphosphate were performed to examine the specificity of the yeast phytases with these substrate analogues. A comparison of kinetic data and the degradation pathways determined gave the first hints about the molecular recognition of inositol hexakisphosphates by the enzymes. Exploitation of the high stereo- and regiospecificity observed in the dephosphorylation of neo- and L-chiro-inositol hexakisphosphate made it possible to establish enzyme-assisted steps for the synthesis of D-neo-inositol 1,2,5,6-tetrakisphosphate, L-chiro-inositol 1,2,3,5,6-pentakisphosphate and L-chiro-inositol 1,2,3,6-tetrakisphosphate.

Common-intermediate strategy for synthesis of conduritols and inositols via beta-hydroxy cyclohexenylsilanes.

[reaction: see text] Syntheses of conduritols B-D and F and d-(+)-chiro- and neo-inositols from cyclohexenylsilane intermediates are described. The key cyclohexylsilane intermediates 5 and 14 were synthesized by stereoselective olefin dihydroxylation of t

Synthesis of D-chiro-3-inosose and (+)-D-chiro-inositol

There are described novel biocatalytic and chemical processes for the synthesis of various oxygenated compounds. Particularly, there are described processes for the synthesis of a useful synthon (12) made by reacting a protected diol (acetonide) with permanganate under appropriate conditions. Such synthon is useful of the synthesis of various pharmaceutically important compounds such as D-chiro-inositol and D-chiro-3-inosose. Also, there are disclosed novel compounds, including specifically the synthon (12) and compounds derived therefrom.

Novel synthesis of enantiomerically pure natural inositols and their diastereoisomers

The various inositol polyphosphates have been found to trigger many important biological processes. Although the knowledge of this phosphoinositide signaling system has been discovered in the past 10 years, many factors remain unclear. For this reason, there is an increased demand for supplies of D-myo-inositol and particularly of novel analogues to investigate these biological mechanisms in more detail. Herein, we report the efficient syntheses of all diastereoisomers of inositol starting with 6-O-acetyl-5-enopyranosides. Conversion of 6-O-acetyl-5-enopyranosides into the corresponding substituted cyclohexanones (Ferrier-II rearrangement) was found to proceed efficiently with a catalytic amount of palladium dichloride. Stereoselective reduction of β-hydroxy ketones obtained provided the precursors to all inositol diastereoisomers in good to excellent yields and with high stereoselectivities. Good accessibility of these enantiomerically pure inositol diastereoisomers results in the efficient syntheses of D-myo-inositol 1,4,5-trisphosphate and D-myo-inositol 1,3,4,5-tetrakisphosphate.

Transformation of cyclohexene to enantiopure cyclitols mediated by sequential oxyselenenylation with (S,S)-hydrobenzoin: Synthesis of D-chiro-inositol and muco-quercitol

Oxyselenenylation of cyclohexene with (S,S)-hydrobenzoin and subsequent oxidation-elimination allows isolation of an allylic ether in which further phenylselenenylation is completely regioselective, thus allowing entry to the cyclitols D-chiro-inositol and muco-quercitol.

A concise synthesis of neo-inositol

neo-Inositol was prepared on a multigram scale in five steps from myo-inositol without recourse to column chromatography. The synthesis includes a large-scale preparation of 1,6:3,4-bis-[O-(2,3-dimethoxybutane-2,3-diyl)]-myo-inositol and a high-yielding i