Spinosin

Base Information

• Chemical Name: Spinosin
• CAS No.: 72063-39-9
• Molecular Formula: C₂₈H₃₂O₁₅
• Molecular Weight: 608.553
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID50222396
• Nikkaji Number: J444.982G
• Wikidata: Q27155298
• Mol file: 72063-39-9.mol

Synonyms:spinosin

Chemical Property of Spinosin

Chemical Property:

• Vapor Pressure: 5.56E-35mmHg at 25°C
• Melting Point: 149 °C
• Refractive Index: 1.733
• Boiling Point: 901.408 °C at 760 mmHg
• PKA: 5.71±0.40(Predicted)
• Flash Point: 296.669 °C
• PSA: 249.20000
• Density: 1.723 g/cm³
• LogP: -1.78110
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated) Pyridine (Slightly)
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 7
• Exact Mass: 608.17412031
• Heavy Atom Count: 43
• Complexity: 987

Purity/Quality:

98%,99%, ^*data from raw suppliers

Spinosin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC=C(C=C3)O)O)C4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)CO)O)O)O
• Isomeric SMILES: COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC=C(C=C3)O)O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• Uses: Spinosin is a C-glycoside flavonoid extracted from Zizhiphi Spinozae, improved pentobarbital-induced sleep.

Technology Process of Spinosin

There total 2 articles about Spinosin 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:

6'',6'''-di-O-((E)-feruloyl)spinosin → (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6,537-98-4) + 6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one (72063-39-9)

Guidance literature:

With ammonium hydroxide; water; In methanol; at 20 ℃; for 1h;

DOI:10.1080/10286020.2011.637491

Reference yield:

6'''-(4'-O-β-D-glucopyranosyl)vanilloyl spinosin (1399718-57-0) → 6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one (72063-39-9)

Guidance literature:

With ammonium hydroxide; In methanol; at 20 ℃; for 1h;

DOI:10.1080/10286020.2011.623128

Reference yield:

6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one (72063-39-9) + methyl iodide (74-88-4) → flavoayamenin nonamethyl ether (60767-82-0)

Guidance literature:

With sodium hydride; 1.) DMSO, 70 deg C, 45 min; r.t., 10 min, 2.) THF, r.t., 20 min;

upstream raw materials:

6'''-(4'-O-β-D-glucopyranosyl)vanilloyl spinosin

Downstream raw materials:

flavoayamenin nonamethyl ether

Refernces

• 1、 Xie, Yuan-Yuan,Xu, Zhi-Lin,Wang, Hui,Kano, Yoshihiro,Yuan, Dan. "A novel spinosin derivative from Semen Ziziphi Spinosae". experimental part. p. 1151 - 1157. Retrieved 2012/02/16.