564-16-9

Basic information

• Product Name: 11-Deoxo-18beta-glycyrrhetic acid
• Synonyms: (3beta,20beta)-3-Hydroxy-olean-12-en-29-oic acid;(3beta,20b)-3-Hydroxy-olean-12-en-29-oic acid;11-Deoxoglycyrrhetic acid;11-Deoxoglycyrrhetinic acid;3β-Hydroxyolean-12-en-30-oic acid;(3beta,5Xi,9xi,18xi)-3-hydroxyolean-12-en-29-oic acid;10-Hydroxy-2,4A,6A,6B,9,9,12A-heptamethyl-1,2,3,4,4A,5,6,6A,6B,7,8,8A,9,10,11,12,12A, 12B,13,14B-eicosahydro-picene-2-carboxylic acid;Epikatonic acid
• CAS NO: 564-16-9
• Molecular Formula: C₃₀H₄₈O₃
• Molecular Weight: 456.7
• Product Categories: Pentacyclic Triterpenes
• Mol File: 564-16-9.mol
• Article Data: 23

Chemical Properties

• Melting Point: 105-107 °C(Solv: methanol (67-56-1))
• Boiling Point: 552.7 °C at 760 mmHg
• Flash Point: 302.1 °C
• Appearance: /
• Density: 1.1 g/cm³
• Vapor Pressure: 1.62E-14mmHg at 25°C
• Refractive Index: 1.557
• PKA: 4.78±0.70(Predicted)
• CAS DataBase Reference: 11-Deoxo-18beta-glycyrrhetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 11-Deoxo-18beta-glycyrrhetic acid(564-16-9)
• EPA Substance Registry System: 11-Deoxo-18beta-glycyrrhetic acid(564-16-9)

Safety Data

• Hazardous Substances Data: 564-16-9(Hazardous Substances Data)

Usage

General Description

11-Deoxo-18beta-glycyrrhetic acid is a triterpenoid compound found in licorice root, with numerous biological activities including anti-inflammatory, anti-cancer, and anti-viral effects. It is a derivative of glycyrrhizic acid, the main active component in licorice root, and has been studied for its potential as a therapeutic agent for various diseases. 11-Deoxo-18beta-glycyrrhetic acid has shown promise in the treatment of skin disorders, viral infections, and cancer, and is being investigated for its potential in pharmaceutical and cosmetic applications. Additionally, 11-Deoxo-18beta-glycyrrhetic acid has been found to have hepatoprotective properties, making it a potential candidate for the treatment of liver diseases. Overall, this compound has garnered significant interest due to its diverse pharmacological properties and potential therapeutic applications.

InChI:InChI=1/C30H48O3/c1-25(2)21-10-13-30(7)22(28(21,5)12-11-23(25)31)9-8-19-20-18-27(4,24(32)33)15-14-26(20,3)16-17-29(19,30)6/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21+,22-,23+,26-,27-,28+,29-,30-/m1/s1

Upstream product

• 657401-74-6 Acetic acid (3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bR)-11-(tert-butyl-dimethyl-silanyloxymethyl)-4,4,6a,6b,8a,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picen-3-yl ester 
• 657401-73-5 (3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bR)-11-(tert-Butyl-dimethyl-silanyloxymethyl)-4,4,6a,6b,8a,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-picen-3-ol 
• 53402-18-9 3β-acetoxy-11-dioxyglycyrrhetic acid 
• 83896-44-0 glycyrrizhin 
• 471-53-4 enoxolone 
• 657401-69-9 acetic acid 11-formyl-4,4a,6a,6b,8a,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-eicosahydropicen-3-yl ester 
• 22477-77-6 acetic acid 11-hydroxymethyl-4,4a,6a,6b,8a,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-eicosahydropicen-3-yl ester 
• 6813-59-8 11-hydroxymethyl-4,4a,6a,6b,8a,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-eicosahydropicen-3-ol 
• 77397-93-4 11-hydroxymethyl-4,4,6a,6b,8a,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-eicosahydro-picene-3,14-diol 

Downstream Products

• 1084889-58-6 (N-cyclohexyl)-11-deoxyglycyrrhetinic acid amide 
• 441759-71-3 diphenylmethyl 2',3',6',2'',3'',4'',6''-heptaacetyl-β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-3-O-11-deoxy-18β-glycyrrhetinate 
• 471-53-4 enoxolone 
• 441759-68-8 diphenylmethyl 11-deoxo-18β-glycyrrhetinate 

Relevant articles and documents

Synthesis, anti-microbial and anti-inflammatory activities of 18β-glycyrrhetinic acid derivatives

Thirteen 18β-glycyrrhetinic acid (GA) derivatives were obtained by reduction at C-11 position, oxidation at C-3 position and condensation at C-2 position of GA. Anti-microbial activity evaluation indicated that compounds 04, 05, 10, 13 and 14 showed more

11-deoxyglycyrrhetinic acid derivatives as well as preparation method and application thereof

The invention belongs to the technical field of drug synthesis, and in particular relates to 11-deoxyglycyrrhetinic acid derivatives as well as a preparation method and application thereof. The invention provides the 11-deoxyglycyrrhetinic acid derivative

Conjugates of 18β-glycyrrhetinic acid derivatives with 3-(1H-benzo[d]imidazol-2-yl)propanoic acid as Pin1 inhibitors displaying anti-prostate cancer ability

Twenty-six conjugates of 18β-glycyrrhetinic acid derivatives with 3-(1H-benzo[d]imidazol-2-yl)propanoic acid were designed and synthesized as Pin1 inhibitors. Most of these semi-synthetic compounds showed improved Pin1 inhibitory activity and anti-proliferative effects against prostate cancer cells as compared to 3-(1H-benzo[d]imidazol-2-yl)propanoic acid and GA. Compounds 10a and 12i were the most potent to inhibit growth of prostate cancer PC-3 with GI50 values of 7.80 μM and 3.52 μM, respectively. The enzyme inhibition ratio of nine compounds at 10 μM was over 90%. Structure-activity relationships indicated that both appropriate structure at ring C of GA and suitable length of linker between GA skeleton and benzimidazole moiety had significant impact on improving activity. Western blot assay revealed that 10a decreased the level of cell cycle regulating protein cyclin D1. Thus, these compounds might represent a novel anti-proliferative agent working through Pin1 inhibition.