CID 115063

Base Information

• Chemical Name: CID 115063
• CAS No.: 60976-49-0
• Molecular Formula: C41H28 O27
• Molecular Weight: 952.657
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID101030289
• Wikipedia: Geraniin
• Wikidata: Q105133605
• Mol file: 60976-49-0.mol

Synonyms:Geraniin

Chemical Property of CID 115063

Chemical Property:

• PKA: 6.35±0.70(Predicted)
• PSA: 450.25000
• Density: 2.25g/cm3
• LogP: -1.10150
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 14
• Hydrogen Bond Acceptor Count: 27
• Rotatable Bond Count: 3
• Exact Mass: 952.08179561
• Heavy Atom Count: 68
• Complexity: 2080

Purity/Quality:

99%, ^*data from raw suppliers

GERANIIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C3C(C(C(O2)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C6=C5C7C(=CC(=O)C(C7(O)O)(O6)O)C(=O)O3)O)O)OC(=O)C8=CC(=C(C(=C8C9=C(C(=C(C=C9C(=O)O1)O)O)O)O)O)O
• Description: Geraniin is a tannin that has been found in P. urinaria and has diverse biological activities. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; IC50s = 0.92 and 1.27 μM at pH 4.5 and 7.9, respectively), superoxide (IC50 = 2.65 μM), and hydroxyl radicals (IC50 = 1.44 μM) in cell-free assays. Geraniin inhibits herpes simplex virus 1 (HSV-1) and HSV-2 replication in plaque reduction assays (IC50s = 35 and 18.4 μM, respectively). It inhibits angiotensin-converting enzyme (ACE) in vitro (IC50 = 13.22 μM) and reduces both systolic and diastolic blood pressure in spontaneously hypertensive rats when administered at a dose of 5 mg/kg. Geraniin (5, 10, and 20 μM) induces apoptosis and halts the cell cycle at the S phase in A549 lung cancer cells. It reduces tumor growth in an A549 mouse xenograft model when administered at doses of 10 and 20 mg/kg.
• Uses: Geraniin protects PC12 cells against neuronal damage and may be used in the treatment of Alzheimer’s disease/ Also is an ACE inhibitor which is useful for hypertension treatment.

Technology Process of CID 115063

There total 4 articles about CID 115063 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:

C46H34O32 → geraniin (60976-49-0) + ascorbic acid (50-81-7,98966-42-8)

Guidance literature:

for 3h; oxidative metabolizm; enzyme from fresh leaves and stems of Geranium thunbergii;

Reference yield:

elaeocarpusin (102382-31-0) → geraniin (81905-83-1) + geraniin (60976-49-0)

Guidance literature:

In water; at 37 ℃; for 18h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1248/cpb.34.4075

Reference yield:

elaeocarpusin (102382-31-0) → geraniin (60976-49-0) + geraniin (81905-83-1)

Guidance literature:

In water; at 90 ℃; for 1h; Yield given; Heating;

upstream raw materials:

elaeocarpusin

Downstream raw materials:

1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-4-O-brevifolincarboxyl-β-D-glucopyranose

1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-2,4-tetrahydroxydibenzofurandicarboxyl-β-D-glucose

1-O-galloyl-2,4;3,6-bis-(R)-4,5,6,4,5,6-hexahydroxydiphenoyl-β-D-glucose

corilagin

Refernces

• 1、 Okuda,Yoshida,Hatano,et al.. "Constituents of Geranium thunbergii SIEB. et ZUCC. XIII. Isolation of water-soluble tannins by centrifugal partition chromatography, and biomimetic synthesis of elaeocarpusin". . p. 4075 - 4082. Retrieved 2007/10/02.
• 2、 Nonaka, Gen-ichiro,Morimoto, Satoshi,Nishioka, Itsuo. "ELAEOCARPUSIN, A PROTO-TYPE OF GERANIIN FROM GERANIUM THUNBERGII". . p. 941 - 943. Retrieved 2007/10/02.