Gymnemagenin

Base Information

• Chemical Name: Gymnemagenin
• CAS No.: 22467-07-8
• Deprecated CAS: 11035-33-9
• Molecular Formula: C30H50 O6
• Molecular Weight: 506.723
• Hs Code.: 1302190200
• UNII: U396WHT2FZ
• Nikkaji Number: J16.125J
• Mol file: 22467-07-8.mol

Synonyms:gymnemagenin

Chemical Property of Gymnemagenin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 330-331℃
• Boiling Point: 634.504°C at 760 mmHg
• PKA: 14.03±0.70(Predicted)
• Flash Point: 261.966°C
• PSA: 121.38000
• Density: 1.23
• LogP: 3.02610
• XLogP3: 4
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 506.36073931
• Heavy Atom Count: 36
• Complexity: 932

Purity/Quality:

98%Min ^*data from raw suppliers

Gymnemagenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC2C3=CCC4C5(CCC(C(C5CCC4(C3(CC(C2(C(C1O)O)CO)O)C)C)(C)CO)O)C)C
• Isomeric SMILES: C[C@]12CC[C@@H]([C@@]([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(C[C@@H]([C@@]5([C@H]4CC([C@H]([C@@H]5O)O)(C)C)CO)O)C)C)(C)CO)O
• Uses: Gymnemagenin is a saponin with a triterpenoid structure, purported to display hypoglycemic and antioxidant effects.

Technology Process of Gymnemagenin

There total 14 articles about Gymnemagenin 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:

3-O-β-D-glucuronopyranosyl gymnemagenin (121686-42-8) → (3β,16β,21β,22α)-olean-12-ene-3,16,21,22,23,28-hexol (22467-07-8) + 3β,16β,21β,23,28-pentahydroxyolean-12-ene (19942-02-0)

Guidance literature:

With sulfuric acid; In methanol; at 100 ℃; for 2h;

DOI:10.1016/j.steroids.2015.01.024

Reference yield:

3-O-β-D-glucuronopyranosyl gymnemagenin (121686-42-8) → (3β,16β,21β,22α)-olean-12-ene-3,16,21,22,23,28-hexol (22467-07-8)

Guidance literature:

In water; at 37 ℃; for 24h; β-glucuronidase (Sigma, type H-2, from Helix pomatia), pH 4.8;

DOI:10.1248/cpb.40.1366

Reference yield:

→ (3β,16β,21β,22α)-olean-12-ene-3,16,21,22,23,28-hexol (22467-07-8)

Guidance literature:

Gemisch v. Genin G, Genin J u. Genin K, KHCO3 / Hydrolyse;

DOI:10.1002/hlca.19670500216

upstream raw materials:

21-O-(4-O-acetyl-3-O-angeloyl)-β-D-fucopyranosyl-22-O-acetyl protoaescigenin

3-O-β-D-glucuronopyranosyl gymnemagenin

3-O-β-D-glucuronopyranosyl gymnemagenin

gymnemic acid II

Downstream raw materials:

16β,28-di-O-acetyl-3β,23;21β,22α,-di-O-isopropylidene-gymnemagenin

C₃₆H₅₈O₆

C₄₀H₆₂O₈

3β,23;21β,22α-di-O-isopropylidenegymnemagenin

Refernces

• 1、 Renga, Barbara,Festa, Carmen,De Marino, Simona,Di Micco, Simone,D'Auria, Maria Valeria,Bifulco, Giuseppe,Fiorucci, Stefano,Zampella, Angela. "Molecular decodification of gymnemic acids from Gymnema sylvestre. Discovery of a new class of liver X receptor antagonists". . p. 121 - 131. Retrieved 2016/09/02.
• 2、 Tsuda, Yoshisuke,Kiuchi, Fumiyuki,Liu, Hong-Min. "ESTABLISHMENT OF THE STRUCTURE OF GYMNEMAGENIN BY X-RAY ANALYSIS AND THE STRUCTURE OF DEACYLGYMNEMIC ACID". . p. 361 - 362. Retrieved 2007/10/02.