18305-96-9

Basic information

• Product Name: 3-(acetyloxy)-11-oxoolean-12-en-29-oic acid
• CAS NO: 18305-96-9
• Molecular Formula: C₃₂H₄₈O₅
• Molecular Weight: 512.7205
• Mol File: 18305-96-9.mol

Chemical Properties

• Boiling Point: 597°C at 760 mmHg
• Flash Point: 183.1°C
• Density: 1.14g/cm³
• Vapor Pressure: 8.52E-16mmHg at 25°C
• Refractive Index: 1.55
• CAS DataBase Reference: 3-(acetyloxy)-11-oxoolean-12-en-29-oic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(acetyloxy)-11-oxoolean-12-en-29-oic acid(18305-96-9)
• EPA Substance Registry System: 3-(acetyloxy)-11-oxoolean-12-en-29-oic acid(18305-96-9)

Safety Data

• Hazardous Substances Data: 18305-96-9(Hazardous Substances Data)

Upstream product

• 471-53-4 enoxolone 
• 75-36-5 acetyl chloride 
• 1405-86-3 glycyrrhizin 
• 64-19-7 acetic acid 
• 53402-18-9 3β-acetoxy-11-dioxyglycyrrhetic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 1620133-40-5 N-(L-phenylalanine tert-butyl ester)-3β-acetyl-11-oxo-olean-12-en-18β-H-30-amide 
• 51298-47-6 N-(L-phenylalanine)-3β-hydroxy-11-oxo-olean-12-en-18β-H-30-amide 
• 1612838-70-6 (cyclohexylamino)-(cyclohexylimino)-methyl 3β-acetyloxy-11-oxo-olean-12-en-30-oate 
• 1477-44-7 methyl glycyrrhetinate 
• 182682-74-2 C₄₀H₅₇N₃O₅S 

Relevant articles and documents

N-methylated diazabicyclo[3.2.2]nonane substituted triterpenoic acids are excellent, hyperbolic and selective inhibitors for butyrylcholinesterase

Triterpenoic acids (oleanolic, ursolic, betulinic, platanic and glycyrrhetinic acid) were acetylated and coupled with 1,3- or 1,4-diazabicyclo[3.2.2]nonanes to yield amides. Reaction of these amides with methyl iodide at the distal nitrogen of the bicyclic system gave the corresponding quaternary ammonium salts. These compounds were shown to act as excellent inhibitors of the enzyme butyrylcholinesterase (BChE) while being only weak inhibitors for acetylcholinesterase (AChE). Evaluation of the enzyme kinetics revealed these compounds to act as hyperbolic inhibitors for BChE while the results from molecular modeling gave an explanation for their selectivity between AChE and BChE.

Design and synthesis of novel glycyrrhetin ureas as anti-inflammatory agents for the treatment of acute kidney injury

To develop new anti-inflammatory drugs for the prevention and treatment of acute kidney injury, a series of novel glycyrrhetic ureas were designed, synthesized and evaluated for anti-inflammatory activity using RAW264.7 cells. Compounds 5r-5u (2.04, 2.50, 3.25 and 2.48 μM, respectively) with acidic or neutral amino acid showed potent anti-inflammatory activity (IC50 = 2–3 μM for NO inhibition), amongst them, compound 5r also inhibited tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) in a dose-dependent manner. In cisplatin-induced AKI mice model, compound 5r significantly reduced the level of pro-inflammatory factors, ameliorated the pathological damage of kidney tissue, and maintained the normal metabolic capacity.

2D- and 3D-QSAR modelling, molecular docking and in vitro evaluation studies on 18β-glycyrrhetinic acid derivatives against triple-negative breast cancer cell line

Triple-negative breast cancers (TNBCs) are one of the most aggressive and complex forms of cancers in women. TNBCs are commonly known for their complex heterogeneity and poor prognosis. The present work aimed to develop a predictive 2D and 3D quantitative structure–activity relationship (QSAR) models against metastatic TNBC cell line. The 2D-QSAR was based on multiple linear regression analysis and validated by Leave-One-Out (LOO) and external test set prediction approach. QSAR model presented regression coefficient values for training set (r2), LOO-based internal regression (q2) and external test set regression (pred_r2) which are 0.84, 0.82 and 0.75, respectively. Five properties, Epsilon4 (electronegativity), ChiV3cluster (valence molecular connectivity index), chi3chain (retention index for three-membered ring), TNN5 (nitrogen atoms separated through 5 bond distance) and nitrogen counts, were identified as important structural features responsible for anticancer activity of MDA-MB-231 inhibitors. Five novel derivatives of glycyrrhetinic acid (GA) named GA-1, GA-2, GA-3, GA-4 and GA-5 were semi-synthesised and screened through the QSAR model. Further, in vitro activities of the derivatives were analysed against human TNBC cell line, MDA-MB-231. The result showed that GA-1 exhibits improved cytotoxic activity to that of parent compound (GA). Further, atomic property field (APF)-based 3D-QSAR and scoring recognise C-30 carboxylic group of GA-1 as major influential factor for its anticancer activity. The significance of C-30 carboxylic group in GA derivatives was also confirmed by molecular docking study against cancer target glyoxalase-I. Finally, the oral bioavailability and toxicity of GA-1 were assessed by computational ADMET studies. Communicated by Ramaswamy H. Sarma.

Nitrogenous heterocyclic glycyrrhetinic acid derivatives, and preparation method and anti-influenza A virus application thereof

The invention discloses nitrogenous heterocyclic glycyrrhetinic acid derivatives, and a preparation method and an anti-influenza A virus application thereof. The glycyrrhetinic acid derivatives comprise a nitrogen heterocyclic ring. A series of the glycyrrhetinic acid derivatives with anti-IAV activity are synthesized. The glycyrrhetinic acid derivatives have strong inhibitory activity on the influenza A virus (IAV), and have obviously stronger inhibitory activity on the influenza A virus than a common positive drug ribavirin, so that the glycyrrhetinic acid derivatives can be used for preparing anti-IAV drugs, and have no side effects.

C3 and C20 diesterified glycyrrhetinic acid derivative, and preparation method and application thereof

The invention provides a C3 and C20 diesterified glycyrrhetinic acid derivative having a structure represented by formula I shown in the description, or a pharmaceutically acceptable salt, a solvate,an optical isomer or a polymorph thereof. Experimental results show that the C3 and C20 diesterified glycyrrhetinic acid derivative has a very good bacteriostatic effect on Staphylococcus aureus, caninhibit Staphylococcus aureus ATCC 6538, Staphylococcus aureus ATCC 12228 and Staphylococcus aureus ATCC 29213, and provides a new choice for anti-infective drugs for Staphylococcus aureus.

Pentacyclic triterpenoid glycyrrhetinic acid derivative as well as preparation method and application thereof

The invention discloses a pentacyclic triterpenoid glycyrrhetinic acid derivative which has a structure as shown in a general formula 1 or a formula 7 in the specification, wherein each substituent isdefined in detail in the specification. The invention also discloses application of the pentacyclic triterpenoid glycyrrhetinic acid derivative in preparation of anti-HCV drugs. Huh7 cytotoxic activity results show that the pentacyclic triterpenoid glycyrrhetinic acid derivative is low in cytotoxicity and has research value. In-vitro anti-HCVcc result shows that glycyrrhetinic acid has relativelyweak anti-HCVcc activity, but the pentacyclic triterpenoid glycyrrhetinic acid derivative has relatively good anti-HCV activity.

Synthesis and Anti-Microbial Activity of Benzylidenhydrazides of Glycyrrethic Acid

Abstract: New derivatives of glycyrrhetic acid with hydrazide pharmacophore groups were synthesized and their antimicrobial activity was evaluated. Hydrazide of 3-O-acetyl-N'-(4-hydroxybenzylidene) glycyrrhetic acid exhibited the highest antimicrobial activity. This compound had both an antibacterial effect against Escherichia coli, Proteus vulgaris, Klebsiella pneumonia, Staphylococcus aureus, Citrobacter diversus, Enterobacter aerogenes, Pseudomonas aeruginosa, and Enterobacter cloacae and antifungal activity against the Candida albicans fungus. The minimum inhibitory concentrations of this compound and pimafucin were similar for Candida albicans.

Derivatization, molecular docking and in vitro acetylcholinesterase inhibitory activity of glycyrrhizin as a selective anti-Alzheimer agent

Acetylcholinesterase inhibitors (AChE-Is) increase both level and duration of action of acetylcholine (ACh); thus, alleviate symptoms of Alzheimer’s disease (AD). Glycyrrhizin, is the main active compound in liquorice root. Its aglycone, glycyrrhetinic acid, has shown several beneficial pharmacological activities. This study reports the synthesis and screening of a series of glycyrrhetinic acid analogs as AChE-Is. Fourteen derivatives were prepared, of which five derivatives are recorded as new viz., 3-phenyl-carbamoyl-18β-glycyrrhetinic acid (J9), 3-acetyl-18β-glycyrrhetinic-30-anilinamide (J10), 3-acetyl-18β-glycyrrhetinic-30-ethanolamide (J11), 3-acetyl-18β-glycyrrhetinic-30-n-butylamide (J12) and 18β-glycyrrhetinic acid-30-prenyl ester (J14), in addition to nine known derivatives (J1-J8 & J13). Compounds J12, J11, J0 and J3 showed remarkable AChE-I activity with IC50 values of 3.43, 5.39, 6.27 and 8.68?μM, respectively. These results are in full agreement with the docking study. The active compounds were non-cytotoxic to normal cells (WI-38).

Chemoenzymatic synthesis of new derivatives of glycyrrhetinic acid with antiviral activity. Molecular docking study

We present an efficient approach to the synthesis of a series of glycyrrhetinic acid derivatives. Six derivatives, five of them new compounds, were obtained through chemoenzymatic reactions in very good to excellent yield. In order to find the optimal reaction conditions, the influence of various parameters such as enzyme source, nucleophile:substrate ratio, enzyme:substrate ratio, solvent and temperature was studied. The excellent results obtained by lipase catalysis made the procedure very efficient considering their advantages such as mild reaction conditions and low environmental impact. Moreover, in order to explain the reactivity of glycyrrhetinic acid and the acetylated derivative to different nucleophiles in the enzymatic reactions, molecular docking studies were carried out. In addition, one of the synthesized compounds exhibited remarkable antiviral activity against TK + and TK- strains of Herpes simplex virus type 1 (HSV-1), sensitive and resistant to acyclovir (ACV) treatment.

Discovery of 18β-glycyrrhetinic acid conjugated aminobenzothiazole derivatives as Hsp90-Cdc37 interaction disruptors that inhibit cell migration and reverse drug resistance

A series of 18β-glycyrrhetinic acid (GA) conjugated aminobenzothiazole derivatives were designed, synthesized and evaluated for disruption activity of Hsp90-Cdc37 as well as the effects of in vitro cell migration. These compounds exhibited relatively good disruption activity against Hsp90-Cdc37 with IC50 values in low micromolar range. A docking study of the most active compound 11g revealed key interactions between 11g and Hsp90-Cdc37 complex in which the benzothiazole moiety and the amine chain group were important for improving activity. It is noteworthy that further antitumor activity screening revealed that some compounds exhibited better inhibitory activity than the commercial anticancer drug 5-FU and showed potent suppression activity against drug-resistant cancer cells. In particular, compound 11 g appeared to be the most potent compound against the A549 cell line, at least partly, by inhibition of the activity of Hsp90 and apoptosis induction. The treatment of A549 cells with compound 11g resulted in inhibition of in vitro cell migration through wound healing assay and S phase of cell cycle arrested. In addition, 11g-induced apoptosis was significantly facilitated in A549 cells. Thus, we conclude that GA aminobenzothiazole derivatives may be the potential Hsp90-Cdc37 disruptors with the ability to suppress cells migration and reversed drug-resistant.