Astilbin

Base Information

• Chemical Name: Astilbin
• CAS No.: 29838-67-3
• Molecular Formula: C₂₁H₂₂O₁₁
• Molecular Weight: 450.399
• Hs Code.: 29389090
• European Community (EC) Number: 694-695-3
• DSSTox Substance ID: DTXSID501019948
• Nikkaji Number: J490.151G
• Wikipedia: Astilbin
• Wikidata: Q4810880
• Metabolomics Workbench ID: 46239
• ChEMBL ID: CHEMBL486017
• Mol file: 29838-67-3.mol

Synonyms:(2R-cis)-isomer of astilbin;(2S-cis)-isomer of astilbin;3-0-alpha-1-rhamnosyl-(2R,3R)-dihydroquercetin;astilbin;isoastilbin;neoisoastilbin

Chemical Property of Astilbin

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 4.42E-27mmHg at 25°C
• Melting Point: 180 °C (decomp)
• Refractive Index: 1.748
• Boiling Point: 801.1 °C at 760 mmHg
• PKA: 7.34±0.60(Predicted)
• Flash Point: 282.9 °C
• PSA: 186.37000
• Density: 1.74 g/cm³
• LogP: 0.03810
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble1mg/mL, clear, colorless
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 3
• Exact Mass: 450.11621151
• Heavy Atom Count: 32
• Complexity: 676

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Astilbin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
• Description: Astilbin is a flavonoid that has been found in S. glabra and has diverse biological activities. It inhibits cisplatin-induced increases in apoptosis and accumulation of reactive oxygen species (ROS) in HEK293 cells when used at a concentration of 200 μM. Astilbin (50 mg/kg) increases renal glutathione (GSH) levels and superoxide dismutase (SOD) and catalase activity and reduces serum creatinine and blood urea nitrogen (BUN) levels, renal IL-1β, IL-6, and TNF-α levels, apoptosis in kidney tissue, and kidney injury in a mouse model of cisplatin-induced nephrotoxicity. It reduces loss of dopaminergic neurons in the substantia nigra and increases striatal GSH levels and SOD activity in a mouse model of MPTP-induced Parkinson''s disease when administered at a dose of 50 mg/kg per day. Astilbin also reduces descent time in a pole test and increases traction test score in a mouse model of Parkinson''s disease, indicating reduced motor deficits. It reduces cell viability of MDA-MB-231 and MCF-7 cells (IC50s = 167.9 and 191.6 μM, respectively), as well as inhibits migration and increases apoptosis when used at concentrations of 50 and 200 μM. Astilbin (20 mg/kg every other day for 14 days) reduces tumor growth in an MCF-7 mouse xenograft model.
• Uses: Astilbin displays anti-depressant activity involving monoaminergic neurotransmitters an the BDNF signal pathway. Anti-oxidant.

Technology Process of Astilbin

There total 8 articles about Astilbin 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: 91.0%

(2R,3R)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman-4-one (294203-79-5) → astilbin (29838-67-3,54081-47-9,54081-48-0,54141-72-9)

Guidance literature:

With hydrogen; palladium; In methanol;

DOI:10.1016/S0040-4039(00)00826-1

Reference yield:

5,7,3',4'-tetra-O-benzyl-(+)-catechin (20728-73-8) → astilbin (29838-67-3,54081-47-9,54081-48-0,54141-72-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / Cp₂HfCl₂; AgClO₄ / CH₂Cl₂ / 2 h / -78 - -35 °C

2: 66 percent / DDQ; H₂O / CH₂Cl₂ / 5 h / 25 °C

3: 85 percent / pyridinium dichromate / CH₂Cl₂ / 40 h / 20 °C

4: 91 percent / H₂ / Pd black / methanol / 50 h / 25 °C

With dipyridinium dichromate; bis(cyclopentadienyl)hafnium dichloride; water; hydrogen; silver perchlorate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium; In methanol; dichloromethane;

DOI:10.1016/j.tet.2003.08.076

Reference yield:

1-O-acetyl-2,3,4-tri-O-benzyl-6-deoxy-α-L-mannose (80152-99-4) → astilbin (29838-67-3,54081-47-9,54081-48-0,54141-72-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / Cp₂HfCl₂; AgClO₄ / CH₂Cl₂ / 2 h / -78 - -35 °C

2: 66 percent / DDQ; H₂O / CH₂Cl₂ / 5 h / 25 °C

3: 85 percent / pyridinium dichromate / CH₂Cl₂ / 40 h / 20 °C

4: 91 percent / H₂ / Pd black / methanol / 50 h / 25 °C

With dipyridinium dichromate; bis(cyclopentadienyl)hafnium dichloride; water; hydrogen; silver perchlorate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium; In methanol; dichloromethane;

DOI:10.1016/j.tet.2003.08.076

upstream raw materials:

astilbin

(2R,3R)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman-4-one

1-O-acetyl-2,3,4-tri-O-benzyl-6-deoxy-α-L-mannose

2,3,4-tris-O-(phenylmethyl)-α-L-rhamnopyranosyl fluoride

Downstream raw materials:

(2R)-2r-(3,4-dimethoxy-phenyl)-5,7-dimethoxy-3t-α-L-rhamnopyranosyloxy-chroman-4-one

(2R)-5,7-diacetoxy-2r-(3,4-diacetoxy-phenyl)-3t-(tri-O-acetyl-α-L-rhamnopyranosyloxy)-chroman-4-one

(2S,3R)-dihydroquercetin 3-O-α-L-rhamnoside

(+/-)-taxifolin

Refernces

• 1、 -. "PROCESS FOR PREPARING FLAVONOIDS". Example 6. . Retrieved 2008/06/13.