ginsenoside F2

Base Information

• Chemical Name: ginsenoside F2
• CAS No.: 62025-49-4
• Molecular Formula: C42H72O13
• Molecular Weight: 785.026
• DSSTox Substance ID: DTXSID20432763
• Nikkaji Number: J38.857B
• Wikidata: Q27146699
• Metabolomics Workbench ID: 122072
• ChEMBL ID: CHEMBL1095007
• Mol file: 62025-49-4.mol

Synonyms:ginsenoside F2;ginsenoside-F2

Chemical Property of ginsenoside F2

Chemical Property:

• Boiling Point: 871.488 °C at 760 mmHg
• PKA: 12.91±0.70(Predicted)
• Flash Point: 480.858 °C
• PSA: 218.99000
• Density: 1.303 g/cm³
• LogP: 2.14900
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 4
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 10
• Exact Mass: 784.49729235
• Heavy Atom Count: 55
• Complexity: 1370

Purity/Quality:

98%Min ^*data from raw suppliers

Ginsenoside F2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)O)C)C)O)C)OC6C(C(C(C(O6)CO)O)O)O)C
• Isomeric SMILES: CC(=CCC[C@@](C)([C@H]1CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)C)O)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C
• Description: Ginsenoside F2 is a ginsenoside that has been found in P. ginseng and has diverse biological activities. It increases the proliferation of human hair dermal papilla cells (HHDPCs) and HaCaT human keratinocytes when used at concentrations of 0.01, 0.1, and 1 μM. Ginsenoside F2 (0.5 and 2.5 mg/kg) induces hair growth and increases hair density following depilation in mice. It is cytotoxic to U373MG glioblastoma cells in vitro (IC50 = 50 μg/ml) and reduces tumor growth in a U373MG mouse xenograft model when administered at a dose of 35 mg/kg every other day. Ginsenoside F2 (1 mg/ear) reduces ear edema induced by phorbol 12-myristate 13-acetate (TPA; ) in mice. It is a human intestinal bacterial metabolite of ginsenoside Rb1 via the intermediate ginsenoside Rd .
• Uses: Ginsenoside F2 is a bioactive metabolite of the ginsenoside component of Panax ginseng with the ability to regulate element-binding protein cleavage activating protein and transforming growth factor-β pathways. This control over apoptosis can lead to a control over hair growth and hair loss in mammals.

Technology Process of ginsenoside F2

There total 15 articles about ginsenoside F2 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: 74.0%

ginsenoside Rd (52705-93-8) → ginsenoside F2 (62025-49-4)

Guidance literature:

With water; at 30 ℃; Microbiological reaction;

DOI:10.1007/s10600-014-1054-1

Reference yield: 58.0%

Ginsenoside Rb1 (41753-43-9,132929-86-3) → ginsenoside F2 (62025-49-4) + 3-O-(β-D-glucopyranosyl)-20-O-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl]-3β,12β,20β-trihydroxydammar-24-ene (80321-69-3)

Guidance literature:

With water; at 30 ℃; for 36h; Microbiological reaction;

DOI:10.1007/s10600-014-1054-1

Reference yield:

Ginsenoside Rb1 (41753-43-9,132929-86-3) → ginsenoside F2 (62025-49-4)

Guidance literature:

With Fusarium oxysporum(YMF_1.02670); In methanol; at 28 ℃; Microbiological reaction;

DOI:10.1002/cbdv.201300005

upstream raw materials:

3,20-di-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)dammar-24-en-3β,12β,20S-triol

(20S)-dammar-24-ene-3α,12β,20-triol

protopanaxadiol

12-β-O-hydroxy-20(S)-hydroxydammarane-24-ene-3-one

Refernces

• 1、 Kim, Yeong-Su,Kim, Do-Yeon,Kang, Dong Wook,Park, Chang-Su. "Hydrolysis of the outer β-(1,2)-d-glucose linkage at the C-3 position of ginsenosides by a commercial β-galactosidase and its use in the production of minor ginsenosides". supporting information. . Retrieved 2018/07/30.
• 2、 Wan, Hui-Da,Li, Dan. "Highly efficient biotransformation of ginsenoside Rb1 and Rg3 using β-galactosidase from Aspergillus sp.". . p. 78874 - 78879. Retrieved 2015/10/05.