6060-06-6

Basic information

• Product Name: platanic acid
• Synonyms: platanic acid;3β-Hydroxy-20-oxo-30-norlupan-28-oic acid
• CAS NO: 6060-06-6
• Molecular Formula: C₂₉H₄₆O₄
• Molecular Weight: 458.67314
• Mol File: 6060-06-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 568.1°C at 760 mmHg
• Flash Point: 311.4°C
• Appearance: /
• Density: 1.106g/cm³
• Vapor Pressure: 2.86E-15mmHg at 25°C
• Refractive Index: 1.534
• CAS DataBase Reference: platanic acid(CAS DataBase Reference)
• NIST Chemistry Reference: platanic acid(6060-06-6)
• EPA Substance Registry System: platanic acid(6060-06-6)

Safety Data

• Hazardous Substances Data: 6060-06-6(Hazardous Substances Data)

Usage

Definition

ChEBI: A pentacyclic triterpenoid that is 30-norlupan-28-oic acid substituted by a 3beta-hydroxy and an oxo group at position 20. It is isolated from the leaves of Syzygium claviflorum and exhibits anti-HIV activity.

InChI:InChI=1/C29H46O4/c1-17(30)18-9-14-29(24(32)33)16-15-27(5)19(23(18)29)7-8-21-26(4)12-11-22(31)25(2,3)20(26)10-13-28(21,27)6/h18-23,31H,7-16H2,1-6H3,(H,32,33)/t18-,19+,20-,21+,22-,23+,26-,27+,28+,29-/m0/s1

Upstream product

• 473-98-3 betulin 
• 472-15-1 Betulinic acid 
• 7790-28-5 sodium periodate 

Downstream Products

• 4356-32-5 methyl (3β)-3-hydroxy-20-oxo-30-norlupan-28-oate 
• 1472003-50-1 (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-benzyl 1-acetyl-9-hydroxy-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysene-3a-carboxylate 
• 1621534-31-3 (1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-benzyl 1-((tert-butoxycarbonyl)amino)-5a,5b,8,8,11a-pentamethyl-9-oxoicosahydro-1H-cyclopenta[a]chrysene-3a-carboxylate 
• 1621534-30-2 (1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-benzyl 1-amino-5a,5b,8,8,11a-pentamethyl-9-oxoicosahydro-1H-cyclopenta[a]chrysene-3a-carboxylate 
• 1621534-29-9 (1R,3aR,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-benzyl 1-((azidocarbonyl)amino)-5a,5b,8,8,11a-pentamethyl-9-oxoicosahydro-1H-cyclopenta[a]chrysene-3a-carboxylate 
• 1621534-28-8 (1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-benzyl 1-((azidocarbonyl)amino)-9-hydroxy-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysene-3a-carboxylate 
• 1621534-27-7 (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-3a-((benzyloxy)carbonyl)-9-hydroxy-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysene-1-carboxylic acid 

Relevant articles and documents

Platanic Acid-Aryl Enones as Potential Anticancer Compounds: Synthesis and Biological Profiling against Breast, Prostate and Lung Cancer Cell Lines

A series of rationally designed platanic acid-based compounds derived from naturally occurring betulinic acid were synthesized through a sequence of Lemieux-Johnson oxidation and Aldol condensation reaction. All the compounds were screened for cytotoxicity against a panel of human cancer and normal cell lines using MTT assay. From the biological data, it was observed that some of these semi-synthetic congeners exhibited potent biological profiles compared to platanic acid. One of the compounds with the p-tolyl substitution was found to be most active in this study, and its cytotoxicity against two of the cell lines, MDA-MB 231 and A-549 were in tune with the standard compound, 5-fluorouracil.

Synthetic Analogues of Betulinic Acid as Potent Inhibitors of PS1/BACE1 Interaction to Reduce Aβ Generation

The lupane-type triterpenoids are endowed with a wide range of biological activities such as antiviral, anti-inflammatory and anticancer activity. We describe here its potential application in Alzheimer's disease (AD) treatment as an inhibitor of PS1/BACE1 interaction. 3-α-Akebonoic acid, which emanated from a high throughput screening (HTS), was discovered to interfere with PS1/BACE1 interaction and reduce amyloid β-protein (Aβ) production. In view of the limited source, we instead used naturally rich betulinic acid (compound 2) as starting material for lead optimization and a focused library of its derivatives was constructed to gain a better understanding of the structure activity relationship (SAR) of triterpenoid-type inhibitor of PS1/BACE1 interaction. Compound 22 was finally chosen as the most potent PS1/BACE1 interaction inhibitor, which reduced Aβ generation effectively.

Structure - Activity relationship study of betulinic acid, a novel and selective TGR5 agonist, and its synthetic derivatives: Potential impact in diabetes

We describe here the biological screening of a collection of natural occurring triterpenoids against the G protein-coupled receptor TGR5, known to be activated by bile acids and which mediates some important cell functions. This work revealed that betulinic (1), oleanolic (2), and ursolic acid (3) exhibited TGR5 agonist activity in a selective manner compared to bile acids, which also activated FXR, the nuclear bile acid receptor. The most potent natural triterpenoid betulinic acid was chosen as a reference compound for an SAR study. Hemisyntheses were performed on the betulinic acid scaffold, and we focused on structural modifications of the C-3 alcohol, the C-17 carboxylic acid, and the C-20 alkene. In particular, structural variations around the C-3 position gave rise to major improvements of potency exemplified with derivatives 18 dia 2 (RG-239) and 19 dia 2. The best derivative was tested in vitro and in vivo, and its biological profile is discussed.