1,3,5-O-Methylidyne-myo-inositol

• CAS: 98510-20-4
• Catalog Number: ACM98510204
• Category: Main Products
• Molecular Weight: 190.15
• Molecular Formula: C₇H₁₀O₆
• Synonyms: myo-inositol 1,3,5-orthoformate; (1R*,3S*,5R*,7S*,8R*,9R*)-2,4,10-trioxatricyclo[3.3.1.13,7]decane-6,8,9-triol; 1,3,5-O-Methylidyne-myo-inositol; 1,3,5-orthoformate-myo-inositol; meso-D-myo-inositol-1,3,5-O-orthoformate; myo-inositol 1,3,5-monoorthoformate; 2,4,10-Trioxatricyclo[3.3.1.13,7]decane-6,8,9-triol
• IUPAC Name: myo-Inositol monoorthoformate
• SMILES: C1(C2C(C3C(C1OC(O2)O3)O)O)O
• InChI Key: WJJFNSGWGPSKAO-UHFFFAOYSA-N
• Boiling Point: 489.7ºC at 760 mmHg
• Melting Point: 260ºC (dec.)(lit.)
• Flash Point: 249.9ºC
• Density: 1.836g/cm³
• Appearance: Colourless crystalline
• Exact Mass: 190.04800
• WGK Germany: 3

Case Study

1,3,5-O-Methylidyne-myo-inositol as Key Synthetic Intermediate for Vascular Calcification Inhibitors

Schantl, Antonia E., et al. Nature communications 11.1 (2020): 721.

1,3,5-O-Methylidyne-myo-inositol serves as a versatile protected scaffold for the synthesis of OEGylated inositol phosphates, enabling the development of potent inhibitors of vascular calcification (VC) with improved pharmacokinetics and safety profiles.
Synthetic Application: The compound was used as the starting material for a three-step synthesis of OEG12-IP5 (a myo-inositol pentakisphosphate conjugated with one oligoethylene glycol chain). Further structural diversification via OEG substitution and phosphate adjustment yielded (OEG2)2-IP4, a lead inhibitor bearing two ethylene glycol units and four phosphate groups.
Performance Evaluation: The derived inhibitor (OEG2)2-IP4 demonstrated superior activity in delaying serum calcification propensity (c350 = 4.9 µM) compared to IP6 (35 µM). It stabilized calciprotein particles in an amorphous state, prevented hydroxyapatite crystal growth, and abrogated vascular smooth muscle cell calcification at ≥1 µM. Subcutaneous administration in rat VC models significantly reduced arterial calcium deposition and improved survival, without affecting serum calcium levels. The rigid methylidyne protection allowed selective functionalization, making this inositol derivative a valuable building block for anti-calcification drug discovery.