488-55-1

Usage

Uses

Used in Plant Biology:
muco-Inositol is used as a vital component in plant biology for the Arabidopsis INOSITOL TRANSPORTER2, which mediates H+ symport of muco-Inositol and Inositol isomers across the plasma membrane in plants. This function is essential for maintaining proper cellular processes and overall plant health.
Used in Food Industry:
In the food industry, muco-Inositol is utilized as a natural ingredient derived from fresh fruit juices. Its presence contributes to the nutritional value and quality of various food products, making it a sought-after additive for a wide range of applications.
Used in Pharmaceutical Research:
muco-Inositol holds potential for pharmaceutical research due to its unique stereoisomer structure. Further studies on its properties and interactions with biological systems may lead to the development of new drugs or therapies targeting specific health conditions.

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

• 6090-97-7 (1R,2S,3R,4S,5S,6S)-6-methoxycyclohexane-1,2,3,4,5-pentol 
• 130669-73-7 (1S,2R,3R,4S,5R,6S)-2,3-dihydroxy-4,5-di-O-isopropylidene-7-oxabicyclo<4.1.0>heptane 
• 34361-60-9 1,2;4,5-Di-O-cyclohexylidene-D-chiro-inositol 
• 75919-47-0 2C₃₃H₆₃N₁₁O₁₅*5H₂O₄S*10H₂O 
• 75933-28-7 C₃₉H₇₅N₁₃O₁₆*3H₂O₄S*6H₂O 
• 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 
• 50474-02-7 1,2:4,5-Dianhydro-cis-inosit 
• 50473-95-5 1,2:4,5-Dianhydro-muco-inosit 
• 139013-60-8 (1S,2R,3R,4R)-3,4-O-Isopropylidenecyclohex-5-ene-1,2,3,4-tetraol 
• 402724-04-3 L-4-O-benzyl-3-O-1,2-O-(2,2,2-trichloroethylidene)-3-O-cyclohexylcarbamoyl-5-O-methyl-muco-inositol 

Downstream Products

• 849670-29-7 hexa-O-benzoyl-myo-inositol 
• 488-66-4 (2R)-2r,3c,4t,5c,6t-pentahydroxy-cyclohexanone 
• 71-43-2 benzene 
• 108-95-2 phenol 
• 23477-46-5 hexa-O-benzoyl-muco-inositol 
• 4099-90-5 myo-inositol hexabenzoate 
• 551-72-4 inositol 

Relevant academic research and scientific papers

VISCUMITOL, A DIMETHYL-ETHER OF MUCO-INOSITOL FROM VISCUM ALBUM

A new di-O-methyl-inositol, named viscumitol, was isolated from Viscum album and the structure established by chemical and spectroscopic means as 1,2-di-O-methyl-muco-inositol.In V. album and other members of the Viscaceae, this cyclitol was stored in high concentrations up to 8.7percent dry weight.Possible physiological functions and chemotaxonomic aspects are briefly discussed. Key Word Index: Viscum album; Viscaceae; cyclitol; 1,2-di-O-methyl-muco-inositol; viscumitol.

Useful access to enantiomerically pure protected inositols from carbohydrates: The aldohexos-5-uloses route

The intramolecular aldol condensation of aldohexos-5-ulose derivatives of the D-xylo and L-ribo stereoseries has been studied. Only one of the four possible inososes was isolated from both stereoseries in reasonable yields (30-38%). The results obtained, together with the previous findings for the L-arabino and L-lyxo stereoseries, allowed for the rationalisation of a mechanism of the reaction based on open-transition-state models and electron-withdrawing inductive effects. Complementary reductions of the intermediate inososes were possible by changing the reaction conditions, and two isomeric inositol derivatives were obtained with complete stereoselection from each inosose. The presented approach permits us to control the configuration of three out of the six stereocentres of the inositol frame and gives access to seven of the nine inositols. Noteworthy, for the D-xylo derivative, the two-step sequence (condensation followed by reduction with NaBH(OAc)3) represents the biomimetic synthesis of myo-inositol. Furthermore, the sugar-based pathway leads directly to enantiomerically pure selectively protected inositols and does not require any desymmetrisation procedure which is needed when myo-inositol and other achiral precursors are employed as starting materials. As an example of application of the method, the indirect selective protection of secondary inositols' hydroxy functions, by placing specific protecting groups on the aldohexos-5-ulose precursor has been presented.

Concentrated hydriodic acid in simultaneous deprotections of multifunctional inositols

L-1-Deoxy-1-fluoro-6-O-methyl-myo-inositol was epimerized by chloral/DCC in boiling 1,2-dichloroethane yielding d-1-O-cyclohexylcarbamoyl-2-deoxy-2-fluoro- 3-O-methyl-5,6-O-[(R/S)-2,2,2-trichloroethylidene]-chiro-inositol. The latter and l-4-O-benzyl-3-O-cyclohexylcarbamoyl-5-O-methyl-1,2-O-(2,2,2- trichloroethylidene)-muco-inositol, l-4-O-benzyl-3-O-cyclohexylcarbamoyl-1,2-O- ethylidene-5-O-methyl-muco-inositol, d-1-O-cyclohexylcarbamoyl-2-deoxy-5,6-O- ethylidene-2-fluoro-3-O-methyl-chiro-inositol, as well as d-5-O-benzyl-4-O- cyclohexylcarbamoyl-3-deoxy-3-(N,N′-dicyclohexylureido)-6-O-methyl-1, 2-O-(2,2,2-trichloroethylidene)-chiro-inositol were deprotected with boiling 57% aq hydrogen iodide. Ether, urethane and ethylidene acetal functions were simultaneously cleaved by the reagent, whereas the trichloroethylidene groups were still intact or were only removed in small quantities. Especially, the urea function of d-5-O-benzyl-4-O-cyclohexylcarbamoyl-3-deoxy-3-(N,N′- dicyclohexylureido)-6-O-methyl-1,2-O-(2,2,2-trichloroethylidene)-chiro-inositol was decomposed to a cyclohexylamino group. The hydrodechlorination of d-1-O-cyclohexylcarbamoyl-2-deoxy-2-fluoro-3-O-methyl-5,6-O-[(R/S)-2,2, 2-trichloroethylidene]-chiro-inositol using Raney-Nickel yielded a mixture of the corresponding 5,6-O-ethylidene- and 5,6-O-chloroethylidene derivatives. The three synthetic steps-hydrodehalogenation, HI-deprotection and peracylation- were combined without purification of the intermediates.

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.

Inositol synthesis: Concise preparation of L-chiro-inositol and muco- inositol from a common intermediate

Fully stereoselective large-scale syntheses have been attained for L- chiro-inositol (2) and muco-inositol (3) by means of controlled peripheral oxygenation of cyclohexadiene diol 1.

Syntheses 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 permaganate 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.

Microbial Oxidation of Aromatics in Enantiocontrolled Synthesis. Part 1.Expedient and General Asymmetric Synthesis of Inositols and Carbohydrates via and Unusual Oxidation of a Polarized Diene with Potassium Permanganate

This paper reports on the details of a general design of carbohydrates and cyclitols from biocatalytically derived synthons.Homochiral 1-halogenocyclohexa-4,6-diene-2,3-diols 1a and 1b have been generated from chloro- and bromobenzene, respectively, by means of bacterial dioxygenase of Pseudomonas putida 39D.These chiral synthons have been manipulated to cyclitols and carbohydrates by further stereoselective functionalizations.The preperation of D-chiro-inositol, neo-inositol, muco-inositol, and allo-inositol exemplifies their use in enantiocontrolled synthesis.A novel oxidation of polarized dienes with KMnO4 resulted in the synthesis of α-halogeno epoxy diols, which proved unexpectedly stable.A mechanism is proposed for this transformation and placed in context with the only four reported examples of this reaction in the literature.In addition to the application of this new chemistry to the synthesis of cyclitols, chloro epoxy diol 21a has been transformed into a series of cyclitol synthons by reductive or hydrolytic operations.Reaction of 21a with ammonia led to the preparation of highly oxygenated pyrazines, whose structure were proven by X-ray crystallography.The use of 21a in the preparation of D-chiro-3-inosose, a hitherto unreported cyclitol derivative, is also reported.In addition, chloro epoxy diol 21a was transformed into D-erythruronolactone, completing the synthesis of this important chiral pool reagent in two operations from chlorobenzene.Oxidative cleavage of tetrol 20 yielded D-mannosolactone identical with an authentic sample.

General Synthesis of Inositols by Hydrolysis of Conduritol Epoxides Obtained Biocatalytically from Halogenobenzenes: (+)-D-chiro-Inositol, allo-Inositol, muco-Inositol and neo-Inositol

Four of the nine isomeric inositols have been prepared by hydrolytic opening of epoxides derived from 3-halogenocyclohexa-3,5-diene-1,2-diol by further oxidation with potassium permanganate or by reduction of chiro-3-inosose (2L-2,3,6/4,5-pentahydroxycyclohexanone).