Morroniside

Base Information

• Chemical Name: Morroniside
• CAS No.: 25406-64-8
• Molecular Formula: C₁₇H₂₆O₁₁
• Molecular Weight: 406.387
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID60948257
• Nikkaji Number: J2.690.257F
• Wikidata: Q27151347
• Metabolomics Workbench ID: 122736
• ChEMBL ID: CHEMBL1209803
• Mol file: 25406-64-8.mol

Synonyms:morroniside

Chemical Property of Morroniside

Chemical Property:

• Vapor Pressure: 7.9E-19mmHg at 25°C
• Melting Point: 133 - 140°C
• Boiling Point: 635.6oC at 760 mmHg
• PKA: 12.54±0.70(Predicted)
• Flash Point: 226.9oC
• PSA: 164.37000
• Density: 1.52
• LogP: -2.42430
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 5
• Exact Mass: 406.14751164
• Heavy Atom Count: 28
• Complexity: 596

Purity/Quality:

95%-98% ^*data from raw suppliers

Morroniside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2C(CC(O1)O)C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)OC
• Isomeric SMILES: C[C@H]1[C@@H]2[C@H](C[C@@H](O1)O)C(=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)OC
• Uses: Morroniside is a pharmaceutical agent improving microvascular functional integrity and vascular elements of the neurovascular unit in the treatment of cerebral ischemia.

Technology Process of Morroniside

There total 8 articles about Morroniside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

<7-O-tosyl-7-epi-(2)H>loganin tetraacetate → morroniside (25406-64-8,52691-03-9,61849-88-5,61849-89-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) DBU; 2.) OsO₄ / 1.) THF, reflux, 67 h; 2.) Et₂O, pyridine, 3 min

2: 15.6 mg / methanolic NaOMe / methanol / 0.5 h

3: 46.8 mg / H₂O / 96 h / biosynthese by feeding to Adina pilulifera

With osmium(VIII) oxide; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; water;

DOI:10.1016/0031-9422(89)80263-8

Reference yield:

(1S,4aS,6R,7R,7aS)-7-Methyl-6-(toluene-4-sulfonyloxy)-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester → morroniside (25406-64-8,52691-03-9,61849-88-5,61849-89-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) DBU; 2.) m-CPBA / 1.) THF, reflux, 67 h; 2.) CH₂Cl₂, rt, 5 h, dark

2: 18.3 mg / methanolic NaOMe / methanol

3: 50.6 mg / H₂O / 96 h / biosynthese by feeding to Adina pilulifera

With sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In methanol; water;

DOI:10.1016/0031-9422(89)80263-8

Reference yield:

C25H33(2)HO15 → morroniside (25406-64-8,52691-03-9,61849-88-5,61849-89-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 15.6 mg / methanolic NaOMe / methanol / 0.5 h

2: 46.8 mg / H₂O / 96 h / biosynthese by feeding to Adina pilulifera

With sodium methylate; In methanol; water;

DOI:10.1016/0031-9422(89)80263-8

Downstream raw materials:

7-O-ethylmorroniside

7-O-methylmorroniside

Refernces