Phyllanthin

Base Information

• Chemical Name: Phyllanthin
• CAS No.: 10351-88-9
• Molecular Formula: C24H34 O6
• Molecular Weight: 418.53
• Hs Code.: 2909309090
• NSC Number: 619043
• UNII: 75O1TFF47Z
• DSSTox Substance ID: DTXSID001319088
• Nikkaji Number: J1.896.977G
• Wikidata: Q27107847
• Metabolomics Workbench ID: 68473
• ChEMBL ID: CHEMBL1253999
• Mol file: 10351-88-9.mol

Synonyms:phyllanthin

Chemical Property of Phyllanthin

Chemical Property:

• Melting Point: 96℃
• Boiling Point: 530.6°Cat760mmHg
• Flash Point: 207.3°C
• PSA: 55.38000
• Density: 1.069g/cm³
• LogP: 4.03140
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 418.23553880
• Heavy Atom Count: 30
• Complexity: 407

Purity/Quality:

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

Phyllanthin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCC(CC1=CC(=C(C=C1)OC)OC)C(CC2=CC(=C(C=C2)OC)OC)COC
• Isomeric SMILES: COC[C@@H](CC1=CC(=C(C=C1)OC)OC)[C@H](CC2=CC(=C(C=C2)OC)OC)COC
• Uses: Phyllanthin is a chemical extract from the Phyllanthus niruri plant and displays pharmacological effects as an anti-diabetic action, anti-arthritic, and inhibitor of P-gp.

Technology Process of Phyllanthin

There total 11 articles about Phyllanthin 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: 54.0%

bromophyllanthin (138737-28-7) → phyllanthin (10351-88-9,40516-27-6,123808-59-3)

Guidance literature:

In tetrahydrofuran; for 3h; ultrasound;

DOI:10.1016/S0040-4020(01)91020-8

Reference yield:

Dg-threo-2.3-bis-(3.4-dimethoxy-benzyl)-succinic acid (15813-34-0,15905-29-0,93609-04-2,126965-32-0) → (+)-phyllanthin (10351-88-9)

Guidance literature:

Multi-step reaction with 3 steps

2: LiAlH₄ / tetrahydrofuran

3: Ag₂O / dimethylformamide

With lithium aluminium tetrahydride; silver(l) oxide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)82594-1

Reference yield:

D,L-2,3-bis(3,4-dimethoxybenzyl)succinic acid (15813-34-0,15905-29-0,93609-04-2,126965-32-0) → (+)-phyllanthin (10351-88-9)

Guidance literature:

Multi-step reaction with 4 steps

3: LiAlH₄ / tetrahydrofuran

4: Ag₂O / dimethylformamide

With lithium aluminium tetrahydride; silver(l) oxide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)82594-1

upstream raw materials:

D_g-threo-2,3-bis-(3,4-dimethoxy-benzyl)-butanediol-(1,4)

methyl iodide

D_g-threo-2.3-bis-(3.4-dimethoxy-benzyl)-succinic acid

D,L-2,3-bis(3,4-dimethoxybenzyl)succinic acid

Downstream raw materials:

(S:S)-1,4-dimethoxy-2,3-bis-(6-bromo-3,4-dimethoxy-benzyl)-butane

(3R,4R)-3,4-Bis-(2-bromo-4,5-dimethoxy-benzyl)-tetrahydro-furan

Refernces

• 1、 Satyanarayana,Venkateswarlu,Viswanatham. "Oxidative aryl-aryl, aryl-benzyl coupling of lignans-reactions of phyllanthin and haloderivatives with TTFA, DDQ, Li/THF)))): Synthesis of dibenzocyclooctadiene system and phyltetralin". . p. 8277 - 8284. Retrieved 2007/10/02.