Lithospermoside

Base Information

• Chemical Name: Lithospermoside
• CAS No.: 63492-69-3
• Molecular Formula: C14H19NO8
• Molecular Weight: 329.307
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID101317116
• Wikidata: Q27155262
• ChEMBL ID: CHEMBL1817899
• Mol file: 63492-69-3.mol

Synonyms:griffonin;griffonin, (4S-(1Z,4alpha,5alpha,6beta))-isomer;lithospermoside

Chemical Property of Lithospermoside

Chemical Property:

• Vapor Pressure: 2.3E-20mmHg at 25°C
• Melting Point: 271ºC (DEC.)
• Refractive Index: 1.654
• Boiling Point: 662.4 °C at 760 mmHg
• PKA: 12.71±0.60(Predicted)
• Flash Point: 354.4 °C
• PSA: 163.63000
• Density: 1.61 g/cm³
• LogP: -3.08692
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: -3.3
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 329.11106656
• Heavy Atom Count: 23
• Complexity: 526

Purity/Quality:

99%, ^*data from raw suppliers

Griffonin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC#N)C(C(C1O)O)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=C/C(=C/C#N)/[C@@H]([C@H]([C@@H]1O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Uses: Griffonin is an extract from the roots of Semiquilegia adoxides which display anti-neutrophilic inflammatory activity.

Technology Process of Lithospermoside

There total 2 articles about Lithospermoside 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: 93.0%

(2Z)-{(4R,5S,6S)-4,5-diacetoxy-6-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile (63568-00-3) → (-)-(2Z)-{(4R,5S,6S)-6-(β-D-glucopyranosyloxy)-4,5-dihydroxycyclohex-2-en-1-ylidene}acetonitrile (63492-69-3,72523-59-2)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃; for 1h;

DOI:10.1002/hlca.200390065

Reference yield:

(2E)-{(4R,5S,6S)-4,5-diacetoxy-6-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile (561023-24-3) → (-)-(2Z)-{(4R,5S,6S)-6-(β-D-glucopyranosyloxy)-4,5-dihydroxycyclohex-2-en-1-ylidene}acetonitrile (63492-69-3,72523-59-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / dioxane / 0.67 h / UV-irradiation

2: 93 percent / NaOMe / methanol / 1 h / 0 °C

With sodium methylate; In 1,4-dioxane; methanol;

DOI:10.1002/hlca.200390065

upstream raw materials:

(2Z)-{(4R,5S,6S)-4,5-diacetoxy-6-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile

(2E)-{(4R,5S,6S)-4,5-diacetoxy-6-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy]cyclohex-2-en-1-ylidene}acetonitrile

Refernces