Protodioscin

Base Information

• Chemical Name: Protodioscin
• CAS No.: 55056-80-9
• Deprecated CAS: 221527-54-4
• Molecular Formula: C51H84O22
• Molecular Weight: 1049.21
• Hs Code.: 29389090
• European Community (EC) Number: 866-818-2
• UNII: D0LC3PH24P
• Nikkaji Number: J445.547I
• Wikipedia: Protodioscin
• Wikidata: Q7251968
• Metabolomics Workbench ID: 53395
• ChEMBL ID: CHEMBL4782480
• Mol file: 55056-80-9.mol

Synonyms:NSC-698 796;NSC698796;protodioscin

Chemical Property of Protodioscin

Chemical Property:

• Appearance/Colour: Brown Yellow Powder
• Melting Point: 190～192℃
• Refractive Index: 1.631
• PKA: 12?+-.0.70(Predicted)
• PSA: 346.06000
• Density: 1.46 g/cm³
• LogP: -1.97970
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly), Pyridine (Slightly)
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 13
• Hydrogen Bond Acceptor Count: 22
• Rotatable Bond Count: 14
• Exact Mass: 1048.54542430
• Heavy Atom Count: 73
• Complexity: 1900

Purity/Quality:

20%-98%, ^*data from raw suppliers

Protodioscin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2C(CC3C2(CCC4C3CC=C5C4(CCC(C5)OC6C(C(C(C(O6)CO)OC7C(C(C(C(O7)C)O)O)O)O)OC8C(C(C(C(O8)C)O)O)O)C)C)OC1(CCC(C)COC9C(C(C(C(O9)CO)O)O)O)O
• Isomeric SMILES: C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O[C@H]7[C@@H]([C@@H]([C@H]([C@@H](O7)C)O)O)O)O)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)C)C)O[C@@]1(CC[C@@H](C)CO[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O
• Recent EU Clinical Trials: A phase IV, 16 weeks, Multicenter, Randomized, Double-Blind, Placebo-Controlled Clinical Trial to assess the efficacy and safety of oral Tribulus terrestris (Tribestan?) in men with erectile dysfunction (mild to moderate) and/or secondary hypoactive sexual desire (low libido)
• Uses: Protodioscin is a steroidal saponin compound found in a number of plant species. It is known to be the active component of the herbal aphrodisiac plant Tribulus terrestris. It has also shown to produce significant increases in the levels of the hormonal levels in animal studies.

Technology Process of Protodioscin

There total 4 articles about Protodioscin 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: 49.0%

(25R)-26-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-16β-acetoxy-22-oxo-cholest-5-en-3β-yl-O-[2,4-di-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-6-O-benzoyl-β-D-glucopyranoside] → protodioscin (55056-80-9)

Guidance literature:

With lithium hydroxide monohydrate; In 1,4-dioxane; water; at 60 ℃; for 6h;

DOI:10.1039/c6ob01766e

Reference yield:

26-O-β-D-glucopyranosyl-22α-methoxyl-(25R)-furost-5-en-3β,26-diol 3-O-α-L-rhamnopyranosyl-(1->2)-O-[α-L-rhamnopyranosyl-(1->4)]-β-D-glucopyranoside → protodioscin (55056-80-9)

Guidance literature:

In water; acetone; at 90 ℃; for 24h;

DOI:10.1016/S0031-9422(96)00750-9

Reference yield:

26-O-β-D-glucopyranosyl-22-O-methylfurost-5-ene-3β,26-diol 3-O-β-chacotrioside (54522-52-0,60478-70-8,139490-48-5) → proto-dioscin (21494-98-4,55056-80-9,60478-69-5,90288-44-1)

Guidance literature:

In water; acetone; for 10h; Heating;

upstream raw materials:

26-O-β-D-glucopyranosyl-22-O-methylfurost-5-ene-3β,26-diol 3-O-β-chacotrioside

C₅₂H₈₆O₂₂

Downstream raw materials:

D-glucose

dioscin

diosgenin 3-O-α-L-rhamnopyranosyl(1->4)-β-D-glucopyranoside

Refernces

• 1、 Hu, Ke,Dong, Ai-Jun,Yao, Xin-Sheng,Kobayashi, Hisayoshi,Iwasaki, Shigeo. "A furostanol glycoside from rhizomes of Dioscorea collettii var. Hypoglauca". . p. 1339 - 1342. Retrieved 2007/10/03.
• 2、 Watanabe, Yoshiaki,Sanada, Shuichi,Ida, Yoshiteru,Shoji, Junzo. "Comparative Studies on the Constituents of Ophiopogonis Tuber and Its Congeners. I. Studies of the Constituents of the Subterranean Part of Liriope platyphylla Wang et Tang.". . p. 1980 - 1990. Retrieved 2007/10/02.