ginsenoside C-K

Base Information

• Chemical Name: ginsenoside C-K
• CAS No.: 39262-14-1
• Deprecated CAS: 79104-63-5,852637-00-4
• Molecular Formula: C36H62 O8
• Molecular Weight: 622.883
• European Community (EC) Number: 683-216-3
• UNII: G8D4792Q7K
• DSSTox Substance ID: DTXSID60431770
• Nikkaji Number: J354.006E
• Wikidata: Q27146701
• ChEMBL ID: CHEMBL3355096
• Mol file: 39262-14-1.mol

Synonyms:20-O-beta-D-glucopyranosyl-20(S)-protopanaxadiol;compound K;compound M1-O;ginsenoside CK;ginsenoside compound K;ginsenoside M1;GM1 saponin

Chemical Property of ginsenoside C-K

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 181～183℃
• Boiling Point: 723.11oC at 760 mmHg
• PKA: 12.94±0.70(Predicted)
• Flash Point: 391.123oC
• PSA: 139.84000
• Density: 1.19
• LogP: 4.32480
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 622.44446893
• Heavy Atom Count: 44
• Complexity: 1070

Purity/Quality:

95%-98% ^*data from raw suppliers

GinsenosideC-K ^*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)O)C)C)O)C)OC5C(C(C(C(O5)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)C)O)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C
• Description: Ginsenoside compound K (C-K) is a metabolite of the protopanaxadiol-type saponins of Panax ginseng C.A. Meyer, has long been used to treat against the development of cancer, inflammation, allergies, and diabetes; C-K acts as a unique HUVEC migration inhibitor by regulating MMP expression, as well as the activity of SPHK1 and its related sphingolipid metabolites. C-K exhibits anti-inflammatory effects by reducing iNOS and COX-2, C-K exhibits an inhibition against the activity of CYP2C9 and CYP2A6 in human liver microsomes with IC50s of 32.0±3.6 μM and 63.6±4.2 μM, respectively. C-K promotes Aβ clearance by enhancing autophagy via the mTOR signaling pathway in primary astrocytes.
• Uses: Ginsenoside C-K is reported to exhibit anti-wrinkle effects. Also, it potentiates tumor necrosis factor (TNF)-related apotosis-inducing ligand (TRAIL)-induced apotosis in HCT116 colon cancer.

Technology Process of ginsenoside C-K

There total 2 articles about ginsenoside C-K 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:

Ginsenoside Rb1 (41753-43-9,132929-86-3) → ginsenoside F2 (62025-49-4) + compound K (39262-14-1)

Guidance literature:

With Fusarium sp.,(YMF_1.02193); In methanol; at 28 ℃; Microbiological reaction;

DOI:10.1002/cbdv.201300005

Reference yield:

ginsenoside Rb2 (11021-13-9,68406-26-8,82166-13-0,82166-14-1,146987-67-9) → ginsenoside F2 (62025-49-4) + compound K (39262-14-1)

Guidance literature:

With recombinant β-glycosidase from Microbacterium sp. Gsoil 167, Ile184Ala, Ile389Ala, Phe390Ala mutant; for 120h; Kinetics; Enzymatic reaction;

DOI:10.1002/cbic.201500004

Reference yield:

compound K (39262-14-1) → C55H81NO16

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 3 h / 40 °C

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 20 °C

3: periodic acid / tetrahydrofuran / 2 h / 20 °C

4: sodium cyanoborohydride / methanol / 1 h / 20 °C / Cooling with ice

With pyridine; sodium cyanoborohydride; periodic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane;

upstream raw materials:

Ginsenoside Rb₁

ginsenoside Rb₂

Refernces

• 1、 Luo, Shao-Liu,Dang, Li-Zhi,Li, Jian-Fang,Zou, Cheng-Gang,Zhang, Ke-Qin,Li, Guo-Hong. "Biotransformation of saponins by endophytes isolated from Panax notoginseng". . p. 2021 - 2031. Retrieved 2013/12/04.