488-55-1

Basic information

• Product Name: muco-Inositol
• CAS NO: 488-55-1
• Molecular Formula: C₆H₁₂O₆
• Molecular Weight: 180.1559
• EINECS: 207-681-5
• Mol File: 488-55-1.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 291.3°Cat760mmHg
• Flash Point: 143.4°C
• Appearance: /
• Density: 2.038g/cm³
• Refractive Index: 1.783
• CAS DataBase Reference: muco-Inositol(CAS DataBase Reference)
• NIST Chemistry Reference: muco-Inositol(488-55-1)
• EPA Substance Registry System: muco-Inositol(488-55-1)

Safety Data

• Hazardous Substances Data: 488-55-1(Hazardous Substances Data)

Usage

Uses

muco-Inositol is a stereoisomer of Inositol (I666000) found in fresh fruit juices. Studies show that Arabidopsis INOSITOL TRANSPORTER2 mediates H+ symport of muco-Inositol and Inositol isomers across plasma membrane in plants.

Definition

ChEBI: An inositol that is cyclohexane-1,2,3,4,5,6-hexol having a (1R,2R,3r,4R,5S,6r)-configuration.

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

• 149820-68-8 1,2-O-isopropylidene-D-chiro-inositol 
• 50473-95-5 1,2:4,5-Dianhydro-muco-inosit 
• 130669-73-7 (1S,2R,3R,4S,5R,6S)-2,3-dihydroxy-4,5-di-O-isopropylidene-7-oxabicyclo<4.1.0>heptane 
• 75919-47-0 2C₃₃H₆₃N₁₁O₁₅*5H₂O₄S*10H₂O 
• 75933-28-7 C₃₉H₇₅N₁₃O₁₆*3H₂O₄S*6H₂O 
• 87-89-8 D-myo-inositol 
• 1214834-30-6 1,3-di-O-benzyl-1L-muco-inositol 
• 283176-83-0 2,4-di-O-benzyl-2L-(2,3,5,6/4)-pentahydroxy-cyclohexanone 
• 148132-86-9 (1R,2S,3S,4R,5S,6S)-1-Chloro-3,4-dihydroxy-5,6-di-O-isopropylidene-1,2-epoxycyclohexane 
• 113973-61-8 1,2,3,6-tetra-O-acetyl-muco-inositol 
• 526-87-4 conduritol A 
• 130669-75-9 (3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole 
• 130669-72-6 (3aS,4R,5S,7aS)-7-bromo-3a,4,5,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,5-diol 
• 139013-60-8 (1S,2R,3R,4R)-3,4-O-Isopropylidenecyclohex-5-ene-1,2,3,4-tetraol 

Downstream Products

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

Relevant articles and documents

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.

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.

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.