Asperosaponin VI

Base Information

• Chemical Name: Asperosaponin VI
• CAS No.: 39524-08-8
• Molecular Formula: C47H76O18
• Molecular Weight: 929.11
• Hs Code.: 29389090
• ChEMBL ID: CHEMBL4521246
• Nikkaji Number: J366.289F
• Wikidata: Q104953785
• Mol file: 39524-08-8.mol

Synonyms:3-O-glucopyranosyl-1-2-arabinopyranosyl-3-norolean-12,20(29)-dien-28-oic acid-28-O-rhamnopyranosyl-1-4-glucopyranosyl-1-6-glucopyranosyl ester;akebia saponin D;asperosaponin VI

Chemical Property of Asperosaponin VI

Chemical Property:

• Melting Point: 234-235 °C
• Boiling Point: 990.2±65.0 °C(Predicted)
• PKA: 12.50±0.70(Predicted)
• Density: 1.43
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: DMSO (Slightly, Sonicated), Methanol (Slightly, Sonicated)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 10
• Exact Mass: 928.50316557
• Heavy Atom Count: 65
• Complexity: 1770

Purity/Quality:

99% ^*data from raw suppliers

Asperosaponin VI ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)CO)OC6C(C(C(CO6)O)O)O)C)C)C2C1)C)C(=O)OC7C(C(C(C(O7)COC8C(C(C(C(O8)CO)O)O)O)O)O)O)C
• Isomeric SMILES: C[C@]12CC[C@@H]([C@@]([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O)O)C)C)(C)CO)O[C@H]8[C@@H]([C@H]([C@H](CO8)O)O)O
• Uses: Asperosaponin VI is a steroidal extract with anti-inflammatory and antinociceptive activity. long term use has been seen to attenuate cardiac dysfunction.

Technology Process of Asperosaponin VI

There total 3 articles about Asperosaponin VI 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:

HN-saponin P (14216-03-6,27013-76-9) → prosapogenin (17184-21-3) + 3-O-<α-L-arabinopyranosyl>hederagenin 28-O-<β-D-glucopyranosyl-(1-6)-β-D-glucopyranoside> (39524-08-8) + hederagenin 28-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester (99624-66-5) + alpha-Hederin (27013-91-8)

Guidance literature:

With sulfuric acid; In ethanol; for 2h; Further byproducts given; Heating;

DOI:10.1248/cpb.33.3473

Reference yield:

hederagenin-3-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1->4)-O-6-O-acetyl-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester (97240-03-4) → 3-O-<α-L-arabinopyranosyl>hederagenin 28-O-<β-D-glucopyranosyl-(1-6)-β-D-glucopyranoside> (39524-08-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 14 mg / 0.1 N aq. KOH / 20 h / Ambient temperature

2: 180 mg / 0.05 N H₂SO₄ / ethanol / 2 h / Heating

With potassium hydroxide; sulfuric acid; In ethanol;

DOI:10.1248/cpb.33.3473

Reference yield:

cauloside D (12672-45-6) → 3-O-<α-L-arabinopyranosyl>hederagenin 28-O-<β-D-glucopyranosyl-(1-6)-β-D-glucopyranoside> (39524-08-8)

Guidance literature:

With hydrogenchloride; for 0.0666667h; Heating;

DOI:10.1016/0031-9422(91)80035-Y

upstream raw materials:

HN-saponin P

cauloside D

hederagenin-3-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1->4)-O-6-O-acetyl-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester

Downstream raw materials:

prosapogenin

3β-[(α-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid 28-β-D-glucopyranosyl ester

Refernces

• 1、 Kizu,Hirabayashi,Suzuki,Tomimori. "Studies on the constituents of Hedera rhombea Bean. IV. On the hederagenin glycosides". . p. 3473 - 3478. Retrieved 2007/10/02.