Ginsenoside Rd

Base Information

• Chemical Name: Ginsenoside Rd
• CAS No.: 52705-93-8
• Molecular Formula: C48H82O18
• Molecular Weight: 947.168
• Hs Code.: 29389090
• European Community (EC) Number: 258-118-5
• UNII: WB232T95AV
• ChEMBL ID: CHEMBL473659
• DSSTox Substance ID: DTXSID301031221
• Metabolomics Workbench ID: 137514
• Nikkaji Number: J61.215D
• Wikidata: Q27136471
• Mol file: 52705-93-8.mol

Synonyms:ginsenoside Rd;ginsenoside-Rd

Chemical Property of Ginsenoside Rd

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 204～206℃
• Refractive Index: 1.61
• Boiling Point: 1020.4 °C at 760 mmHg
• PKA: 12.85±0.70(Predicted)
• Flash Point: 570.9 °C
• PSA: 298.14000
• Density: 1.37 g/cm³
• LogP: -0.02680
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 12
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 13
• Exact Mass: 946.55011576
• Heavy Atom Count: 66
• Complexity: 1680

Purity/Quality:

99%, ^*data from raw suppliers

Ginsenoside Rd ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 2-45

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)OC6C(C(C(C(O6)CO)O)O)O)C)C)O)C)OC7C(C(C(C(O7)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@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)O)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C
• Description: Ginsenosides are pharmacologically active natural constituents of ginseng and other plants of the genus Panax. Structurally, they are steroid glycosides derived from the triterpene squalene. Ginsenoside Rd is a protopanaxadiol which is more abundant in some Panax species (e.g., P. quinquefolium) than others. This ginsenoside has diverse in vitro and in vivo effects, including cardioprotective, neuroprotective, and anti-inflammatory actions. Notably, ginsenoside Rd is converted to other ginsenosides in response to steaming or heating plant materials, leading to loss of these activities.
• Uses: Ginsenoside RD has been shown to attenuate tau protein phosphorylation via the PI3K/AKT/GSK-3β pathway after forebrain ischemia. This could be used to counter the risk of developing post-stroke dementia.

Technology Process of Ginsenoside Rd

There total 9 articles about Ginsenoside Rd 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: 95.0%

Ginsenoside Rb1 (41753-43-9,132929-86-3) → ginsenoside Rd (52705-93-8)

Guidance literature:

With β-glucosidase from Thermotoga thermarum DSM 5069T; In aq. buffer; at 90 ℃; for 1h; pH=4.8; Kinetics; Enzymatic reaction;

DOI:10.1016/j.molcatb.2013.05.027

Reference yield:

ginsenoside Rc → ginsenoside Rg3 (14197-60-5,38243-03-7,126252-51-5) + ginsenoside Rd (52705-93-8)

Guidance literature:

With Bacterium Leuconostoc sp. BG₇₈; In aq. phosphate buffer; at 37 ℃; pH=7; Microbiological reaction;

DOI:10.1007/s10600-014-1018-5

Reference yield:

Ginsenoside Rb1 (41753-43-9,132929-86-3) → ginsenoside F2 (62025-49-4) + ginsenoside Rd (52705-93-8)

Guidance literature:

With recombinant β-glycosidase from Microbacterium sp. Gsoil 167, wild-type; for 24h; Enzymatic reaction;

DOI:10.1002/cbic.201500004

upstream raw materials:

malonyl-ginsenoside Rb₁

(3β,12β,20S)-3-[(6-O-acetyl-β-D-glucopyranosyl-(1->2)-β-D-glucopyranosyl)oxy]-20-[(β-D-glucopyranosyl)oxy]dammar-24-en-12-ol

Ginsenoside Rb₁

Ginsenoside Rb₃

Downstream raw materials:

vina-ginsenoside-R8

20(R)-ginsenoside Rg₃

ginsenoside Rg₃

ginsenoside F₂

Refernces

• 1、 Zhao, Linguo,Xie, Jingcong,Zhang, Xuesong,Cao, Fuliang,Pei, Jianjun. "Overexpression and characterization of a glucose-tolerant β-glucosidase from Thermotoga thermarum DSM 5069T with high catalytic efficiency of ginsenoside Rb1 to Rd". . p. 62 - 69. Retrieved 2013.
• 2、 Guo, Zi Yu,Luo, Zhi Yong,Tan, Shi Quan,Tian, Liang Yu,Weng, Pei,Zhang, Bian Ling,Zhang, Ru. "Two key amino acids variant of α-l-arabinofuranosidase from bacillus subtilis str. 168 with altered activity for selective conversion ginsenoside rc to rd". . . Retrieved 2021/06/16.
• 3、 Ten,Chae,Yoo. "Transformation of ginsenoside Rc into (20S)-Rg3 by the bacterium leuconostoc sp. BG78". . p. 562 - 564. Retrieved 2014/08/18.