551-72-4

Usage

Uses

Used in Pharmaceutical Research:
L-(-)-CHIRO-INOSITOL is used as a research compound for its potential role in modulating amyloid-β aggregation, which is associated with neurodegenerative diseases such as Alzheimer's.
Used in Diabetes Research:
L-(-)-CHIRO-INOSITOL is used as a research compound for its in vitro insulin-like effect and its ability to enhance glucose uptake in muscle cells. This is achieved through the induced translocation of glucose transporter 4, which is crucial for maintaining proper glucose homeostasis and managing diabetes.
Used in Chemical Synthesis:
L-(-)-CHIRO-INOSITOL, due to its unique chemical structure, is used as a building block or intermediate in the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Nutritional Supplements:
L-(-)-CHIRO-INOSITOL is used as an ingredient in nutritional supplements, particularly those aimed at supporting insulin sensitivity and glucose metabolism.
Used in Food Industry:
L-(-)-CHIRO-INOSITOL may be used in the food industry as a natural sweetener or as an additive to improve the texture and stability of certain products.
Used in Cosmetics:
L-(-)-CHIRO-INOSITOL could be utilized in the cosmetics industry for its potential skin health benefits, such as improving skin hydration and elasticity.

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+/m1/s1

Upstream product

• 38876-99-2 1L-chiro-inositol 
• 488-54-0 D-chiro-inositol 
• 488-59-5 myo-inositol 
• 1254-38-2 inositol peracetate 
• 7664-41-7 ammonia 
• 7732-18-5 water 
• 608-80-0 benzenehexol 
• 75919-47-0 2C₃₃H₆₃N₁₁O₁₅*5H₂O₄S*10H₂O 
• 75933-28-7 C₃₉H₇₅N₁₃O₁₆*3H₂O₄S*6H₂O 
• 149820-68-8 1,2-O-isopropylidene-D-chiro-inositol 
• 132891-77-1 6-O-Camphanoyl-1,2;4,5-di-O-cyclohexylidene-D-chiro-inositol 
• 132891-77-1 6-O-Camphanoyl-1,2;4,5-di-O-cyclohexylidene-D-myo-inositol 
• 129115-29-3 6-O-Camphanoyl-1,2;4,5-di-O-cyclohexylidene-3-O-trifluoromethanesulfonyl-D-myo-inositol 
• 129094-32-2 1,2;4,5-Di-O-cyclohexylidene-3-O-trifluoromethanesulfonyl-myo-inositol 

Downstream Products

• 849585-22-4 LACTIC ACID 
• 319-89-1 tetrahydroxy-1,4-quinone 
• 79-33-4 L-Lactic acid 
• 133-37-9 DL-tartaric acid 
• 527-00-4 allo-mucic acid 
• 87-73-0 DL-glucaric acid 
• 110-15-6 succinic acid 
• 83-86-3 phytic acid 
• 925665-97-0 hexa-O-nitro-myo-inositol 
• 19669-12-6 1,2,3,4,5-pentaacetoxy-6-chloro-cyclohexane 
• 17230-39-6 1-O-methyl-myo-inositol pentaacetate 
• 31429-11-5 Inosit-hexakis-dichloracetat 
• 609-23-4 2,4,6-Triiodophenol 
• 20770-56-3 penta-O-benzoyl-myo-inositol 

Relevant academic research and scientific papers

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.

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.

Optically active phenoxypropionic esters

Optically active compounds of the formula I STR1 where R is C1 -C12 -alkyl or -perfluoroalkyl in which one or two non-adjacent CH2 or CF2 groups can also be replaced by --O-- and/or --CO-- and/or --CO--O-- and/or --CH=CH-- and/or --CH-halogen-- and/or --CHCN-- and/or --0--CO--CH-halogen-- and/or --O--CO--CHCN--, or is C1 -C12 -alkyl which can have a terminal chemically reactive group and in which a CH2 group can be replaced by --O--, A1 and A2 are each, independently of one another, 1,4-phenylene which is unsubstituted or substituted by one or two F and/or Cl and/or Br atoms and/or CH3 groups and/or CN groups and in which one or two CH groups can also be replaced by N, 1,4-cyclohexylene in which one or two non-adjacent CH2 groups can also be replaced by --O-- and/or --S--, 1,4-piperidinediyl, 1,4-bicyclo[2.2.2]octylene, 2,6-naphthalenediyl, decahydro-2,6-naphthalenediyl or 1,2,3,4-tetrahydro-2,6-naphthalenediyl, A3 is unsubstituted or substituted phenyl, Z is --CO--O--, --O--CO--, --CH2 CH2 --, --OCH2 --, --CH2 O--, --C C-- or a single bond and m is 0, 1, 2 or 3.

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).

GLYCOSYL-INOSITOL DERIVATIVES III. SYNTHESIS OF HEXOSAMINE-INOSITOL-PHOSPHATES RELATED TO PUTATIVE INSULIN MEDIATORS

The disaccharides related to glycosyl phosphatidyl inositol anchors of membrane proteins, 4-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol-1-phosphate and 4-O-(2-amino-2-deoxy-α-D-galactopyranosyl)-D-chiro-inositol-1-phosphate, have been prepared from optically resolved myo-inositol derivatives.The chiro-inositol moiety was obtained by epimerization of a selectively blocked myo-inositol-triflate ester.The resolved inositols were subsequently phosphorylated to yield the disaccharide aglycones.The amino-sugar components were prepared by azidonitration of suitably protected glucal and galactal derivatives.The derived pyranosyl chlorides were then condensed with the inositol phosphates using silver triflate as the promoter.

NOVEL BIOSYNTHESIS OF D-PINITOL IN SIMMONDSIA CHINENSIS

Chase experiments with 14CO2 and feeding experiments with labwelled inositols showed that D-pinitol in leaves of Simmondsia chinensis arises via epimerization of D-ononitol.This finding represents an alternative pathway, since D-pinitol is formed in gymnosperms and other plants by epimerization of sequoyitol.Key Word Index -- Simmondsia chinensis; Simmondsiaceae; jojoba; biosynthesis; cyclitols; D-pinitol; D-ononitol.

PURIFICATION AND STRUCTURE DETERMINATION OF THREE α-D-GALACTOPYRANOSYLCYCLITOLS FROM SOYA BEAN

Three α-D-galactopyranosylcyclitols previously isolated from soya bean are shown to be 1D-2-O-(α-D-galactopyranosyl)-4-O-methyl-chiro-inositol, 1D-5-O-(α-D-galactopyranosyl)-4-O-methyl-chiro-inositol, and 1D-2-O-(α-D-galactopyranosyl)-chiro-inositol.Assignments of the (13)C-n.m.r. spectra of these compounds and of 1L-1-O-(α-D-galactopyranosyl)-myo-inositol (galactinol) are presented.The mass spectra of derivatives prepared by permethylation or perdeuteriomethylation, followed by hydrolysis and acetylation or methylation are discussed.