523-92-2

Basic information

• Product Name: 5-O-Methyl-myo-inositol
• Synonyms: SEQUOYITOL;5-O-METHYL-MYO-INOSITOL;SEQUOYITOL 90%;myo-Inositol, 5-O-methyl-;(1S,2R,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol
• CAS NO: 523-92-2
• Molecular Formula: C₇H₁₄O₆
• Molecular Weight: 194.18
• EINECS: 208-352-9
• Product Categories: Anthraquinones, Hydroquinones and Quinones
• Mol File: 523-92-2.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 317.2°C at 760mmHg
• Flash Point: 145.6°C
• Appearance: /
• Density: 1.56g/cm³
• Vapor Pressure: 3.28E-05mmHg at 25°C
• Refractive Index: 1.588
• Storage Temp.: Refrigerator
• Solubility: Water
• CAS DataBase Reference: 5-O-Methyl-myo-inositol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-O-Methyl-myo-inositol(523-92-2)
• EPA Substance Registry System: 5-O-Methyl-myo-inositol(523-92-2)

Safety Data

• Hazardous Substances Data: 523-92-2(Hazardous Substances Data)

Usage

Uses

5-O-Methyl-myo-inositol or Sequoyitol is used in the treatment of diabetes, decreasing blood glucose, improving glucose intolerance and improving insulin signalling.

InChI:InChI=1/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2?,3-,4+,5+,6-,7?

Upstream product

• 97-30-3 methyl-alpha-D-glucopyranoside 
• 940000-68-0 6,8,9-tris-benzyloxy-3-phenyl-2,4-dioxa-bicyclo[3.3.1]nonan-7-ol 
• 111015-74-8 DL-1,3-di-O-benzoyl-4-O-methyl-chiro-inositol 
• 111392-30-4 1-O-allyl-4-O-methyl-myo-inositol 
• 133218-74-3 4,5,6-tri-O-benzyl-1,2-anhydro-myo-inositol 
• 102997-58-0 (1R,2R,3S)-tris(phenylmethoxy)-6S-hydroxy-cyclohex-4-ene 
• 135267-00-4 1-O-Allyl-2,3,4-tri-O-benzyl-D-chiro-inositol 
• 85798-11-4 (4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one 
• 642-38-6 quebrachitol 
• 111392-29-1 (3aS,4S,4aS,7aS,8S,8aR)-4-Allyloxy-8-methoxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxole 
• 111392-09-7 (1S,2R,3S,4R,5R,6S)-3,4,6-Tris-allyloxy-5-benzyloxy-cyclohexane-1,2-diol 
• 98925-52-1 (+/-)-5,6-di-O-allyl-1,4-di-O-benzyl-myo-inositol 
• 58706-20-0 (+/-)-3,6-di-O-benzyl-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 98906-25-3 (±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol 

Downstream Products

• 92379-84-5 5-O-Methyl-myo-inosose-⁽²⁾; 4-O-Methyl-scyllo-inosose 
• 1254-38-2 inositol peracetate 
• 14199-75-8 (1S,2R,3S,4S,5R,6S)-1-Methoxy-2,3,4,5,6-pentakis-trimethylsilanyloxy-cyclohexane 
• 20254-33-5 1,2,3,4,6-penta-O-acetyl-5-O-methyl-myo-inositol 
• 54324-59-3 2,3,4,5,6-Penta-O-acetyl-1-O-methyl-myo-inositol 
• 87-89-8 D-myo-inositol 
• 91470-19-8 2-Desoxy-5-O-methyl-myo-inosit 
• 14199-75-8 (1R,2S,3R,4R,5S,6S)-1-Methoxy-2,3,4,5,6-pentakis-trimethylsilanyloxy-cyclohexane 

Relevant articles and documents

Lipase Regioselective O-Acetylations of a myo-Inositol Derivative: Efficient Desymmetrization of 1,3-Di-O-benzyl-myo-inositol

Chiral myo-inositol derivatives play key roles in cell-signaling processes. Despite the relevance of these compounds, few syntheses of them rely on enantioselective catalytic reactions. Even fewer reports describe the use of desymmetrization of myo-inositol derivatives. In fact, most routes involve resolution by derivatization. Thus, a symmetrical partially protected myo-inositol derivative, 1,3-di-O-benzyl-myo-inositol (1), was used as a substrate in fast lipase-catalyzed desymmetrization reactions. Among the lipases tested, both Lipozyme RM-IM and Lipozyme TL-IM were effective in catalyzing the formation of the chiral acetate l-(+)-6-O-acetyl-1,3-di-O-benzyl-myo-inositol [l-(+)-2] with high conversion (98–99 %) and ee (>99 %). Conversely, Novozyme 435 and Lipomod 34P as biocatalysts showed different regioselectivity, leading to the formation of the symmetrical 5-O-acetylated product. We were able to reuse TL-IM lipase seven times without any noticeable decrease in the conversion. Acetate l-(+)-2 is a potential precursor of biologically active myo-inositol derivatives and other relevant materials for cell biology studies.

Stereoselective oxidation of protected inositol derivatives catalyzed by inositol dehydrogenase from Bacillus subtilis

Inositol dehydrogenase (EC 1.1.1.18) from Bacillus subtilis is shown to have a nonpolar cavity adjacent to the active site, allowing racemic protected inositol derivatives such as 4-O-benzyl-myo-inositol to be recognized with very high apparent stereoselectivity.

An effective strategy for the synthesis of 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro- and -D-myo-inositol 1-phosphate related to putative insulin mimetics

Two glycosylinositol phosphates related to putative insulin mimetics, 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro-inositol 1-phosphate (1) and 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate (2), have been synthesized from selectively protected and enantiomerically pure D-chiro- and myo-inositol derivatives. The D-chiro-inositol unit was prepared in a multigram scale from D-glucose using the Ferrier's carbocyclization route, and it was transformed into the corresponding myo epimer by an oxidation-reduction sequence. The trichloroacetimidate method was applied efficiently for the key glycosylation of the inositol derivatives.