2,3,23-Trihydroxy-29-methoxy-29-oxoolean-12-en-28-oic acid

Base Information

• Chemical Name: 2,3,23-Trihydroxy-29-methoxy-29-oxoolean-12-en-28-oic acid
• CAS No.: 1802-12-6
• Molecular Formula: C₃₁H₄₈O₇
• Molecular Weight: 532.718
• NSC Number: 116453
• DSSTox Substance ID: DTXSID40939305
• Wikidata: Q104972385
• Mol file: 1802-12-6.mol

Synonyms:NSC-116453;NSC116453;2,3,23-trihydroxy-29-methoxy-29-oxoolean-12-en-28-oic acid;DTXSID40939305;FT-0697857

Chemical Property of 2,3,23-Trihydroxy-29-methoxy-29-oxoolean-12-en-28-oic acid

Chemical Property:

• Vapor Pressure: 4.73E-19mmHg at 25°C
• Refractive Index: 1.582
• Boiling Point: 639.6 °C at 760 mmHg
• Flash Point: 199.3 °C
• PSA: 124.29000
• Density: 1.24 g/cm³
• LogP: 4.32990
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 532.34000387
• Heavy Atom Count: 38
• Complexity: 1050

Purity/Quality:

98%,99%, ^*data from raw suppliers

Phytolaccagenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CC(C(C5(C)CO)O)O)C)C)C2C1)C)C(=O)O)C(=O)OC
• Uses: Phytolaccagenin (CAS# 1802-12-6) is a saponin found in Phytolacca acinosa and Phytolacca americana species which have antiproliferative activities in humans.

Technology Process of 2,3,23-Trihydroxy-29-methoxy-29-oxoolean-12-en-28-oic acid

There total 5 articles about 2,3,23-Trihydroxy-29-methoxy-29-oxoolean-12-en-28-oic acid 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: 99.5%

3-O-(β-D-glucopyranosyl-(1->4)-β-D-xylopyranosyl)-phytolaccagenin (65497-07-6) → phytolaccagenine (1802-12-6)

Guidance literature:

With hydrogenchloride; water; In methanol; at 4 ℃; for 20h;

DOI:10.1002/cbdv.201000339

Reference yield: 81.1%

EsA (65497-07-6) → Jaligonicacid-30-methylester (1802-12-6)

Guidance literature:

With hydrogenchloride; In water;

Reference yield:

Oleanolic acid (508-02-1) → phytolaccagenine (1802-12-6) + (2S,4aR,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-11-hydroxy-9-(hydroxymethyl)-2 methoxycarbonyl-2,6a,6b,9,12a-pentamethyl-10-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid (60820-94-2)

Guidance literature:

With Streptomyces griseus ATCC 13273; for 144h; Culture medium; Enzymatic reaction;

DOI:10.1016/j.tet.2011.04.055

upstream raw materials:

EsA

Oleanolic acid

3-O-(β-D-glucopyranosyl-(1->4)-β-D-xylopyranosyl)-phytolaccagenin

Downstream raw materials:

methyl (2β,3β)-28-{[3-(benzoylamino)propyl]amino}-2,3,23-trihydroxy-28-oxoolean-12-en-30-oate

methyl (2β,3β)-2,3,23-trihydroxy-28-({3-[(4-methylbenzoyl)amino]propyl}amino)-28-oxoolean-12-en-30-oate

methyl (2β,3β)-2,3,23-trihydroxy-28-({3-[ (4-hydroxybenzoyl)amino]propyl}amino)-28-oxoolean-12-en-30-oate

methyl (2β,3β)-2,3,23-trihydroxy-28-({3-[(4-methoxybenzoyl)amino]propyl}amino)-28-oxoolean-12-en-30-oate

Refernces

• 1、 Gong, Wei,Jiang, Zhihui,Sun, Peng,Li, Ling,Jin, Yongsheng,Shao, Lucheng,Zhang, Wen,Liu, Baoshu,Zhang, Hongwei,Tang, Hua,Chen, Yufeng,Yi, Yanghua,Zhang, Dazhi. "Synthesis of novel derivatives of esculentoside A and its aglycone phytolaccagenin, and evaluation of their haemolytic activity and inhibition of lipopolysaccharide-induced nitric oxide production". experimental part. p. 1833 - 1852. Retrieved 2012/01/14.