Linarin

Base Information

• Chemical Name: Linarin
• CAS No.: 480-36-4
• Molecular Formula: C28H32O14
• Molecular Weight: 592.554
• Hs Code.: 29389090
• European Community (EC) Number: 207-547-6
• UNII: HBH2I685IU
• DSSTox Substance ID: DTXSID40197382
• Nikkaji Number: J6.164F
• Wikidata: Q1775837
• Metabolomics Workbench ID: 140770
• ChEMBL ID: CHEMBL509502
• Mol file: 480-36-4.mol

Synonyms:acaciin;linarin

Chemical Property of Linarin

Chemical Property:

• Appearance/Colour: white to off white powder
• Melting Point: 258-260 °C
• Boiling Point: 885.2 °C at 760 mmHg
• PKA: 6.11±0.40(Predicted)
• Flash Point: 292.2 °C
• PSA: 217.97000
• Density: 1.62 g/cm³
• LogP: -0.79530
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Acetic Acid (Very Slightly, Heated), Acetonitrile (Slightly), DMSO (Slightly), M
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 7
• Exact Mass: 592.17920569
• Heavy Atom Count: 42
• Complexity: 955

Purity/Quality:

95%-98% ^*data from raw suppliers

Linarine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)OC)O)O)O)O)O)O)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)OC)O)O)O)O)O)O)O
• Uses: Linarine (Diosmin EP Impurity E) is a naturally occurring flavone glycoside that was identified to possess potential sedative and anticonvulsant properties.

Technology Process of Linarin

There total 4 articles about Linarin 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: 53.0%

3'-O-(1-phenyltetrazol-5-yl)diosmin (771480-96-7) → acacetin 7-O-rutinoside (480-36-4)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In methanol; for 5h; Heating;

DOI:10.1021/np040079b

Reference yield:

diosmin (520-27-4) → acacetin 7-O-rutinoside (480-36-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / KHCO₃ / dimethylformamide / 2 h / 80 °C

2: 53 percent / HCOONH₄ / Pd/C / methanol / 5 h / Heating

With ammonium formate; potassium hydrogencarbonate; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/np040079b

Reference yield:

5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one (480-44-4) + O2,O3,O4-triacetyl-O6-(tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranosyl bromide (4154-21-6) → acacetin 7-O-rutinoside (480-36-4)

Guidance literature:

With potassium hydroxide; acetone; Erhitzen des Reaktionsprodukts mit Acetanhydrid und Pyridin und Erwaermen des isolierten Reaktionsprodukts mit wss.-aethanol. Natronlauge;

upstream raw materials:

5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one

O²,O³,O⁴-triacetyl-O⁶-(tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranosyl bromide

3'-O-(1-phenyltetrazol-5-yl)diosmin

diosmin

Downstream raw materials:

linarin heptaacetate

5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one

7,4'-dimethoxy-5-hydroxy-6-iodoflavone

5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Refernces