Enoxolone

Base Information

• Chemical Name: Enoxolone
• CAS No.: 471-53-4
• Molecular Formula: C30H46O4
• Molecular Weight: 470.693
• Hs Code.: 29189900
• NSC Number: 757815
• RXCUI: 1311506
• ChEMBL ID: CHEMBL109757
• Mol file: 471-53-4.mol

Synonyms:Uralenic acid;(2S,4aR,6aS,6aS,6bR,8aS,10R,12aS,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate;Biosone;Hidermart;Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3β,20β)-;Glycyrrhetic acid;3-Glycyrrhetinic acid;Glycyrrhetinate;10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid;β-Glycyrrhetinic Acid;Hidermart (TN);Glycyrrhetin;r-Glycyrrhetinic acid;Glycyrrhetinic acid;Glycyrrhetinic acid (JAN);(3β)-3-Hydroxy-11-oxoolean-12-en-30-oic acid;

Chemical Property of Enoxolone

Chemical Property:

• Appearance/Colour: white or greyish-white crystalline powder
• Vapor Pressure: 2.71E-16mmHg at 25°C
• Melting Point: 292-295 °C(lit.)
• Refractive Index: 162 ° (C=1, MeOH)
• Boiling Point: 588.3 °C at 760 mmHg
• PKA: pKa 5.56±0.1 (Uncertain)
• Flash Point: 323.7 °C
• PSA: 74.60000
• Density: 1.14 g/cm³
• LogP: 6.41260
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, soluble in ethanol, sparingly soluble in methylene chloride.
• Water Solubility.: SOLUBLE IN ACETIC ACID
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 470.33960994
• Heavy Atom Count: 34
• Complexity: 965

Purity/Quality:

99% up, ^*data from raw suppliers

Glycyrrhetinic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC3(C(C2(CCC1O)C)C(=O)C=C4C3(CCC5(C4CC(CC5)(C)C(=O)O)C)C)C)C
• Isomeric SMILES: C[C@]12CC[C@](C[C@H]1C3=CC(=O)C4[C@]5(CC[C@@H](C(C5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)(C)C(=O)O
• Description: Extracting from liquorice (Glycyrrhiza uralensis Fisch, Gan Cao), glycyrrhetic acid also can be detected in other plants, such as Abrus cantoniensis Hance and Herba Abri fruticulosi. As one of traditional Chinese medicines, liquorice has been applied clinically for a long period. Due to its extensive usage, it plays an extremely important role in traditional Chinese medicine formula mainly as “guide” drug. As is recorded in Shen Nong’s Herbal Classic and later in pharmaceutical monographs, liquorice is able to strengthen bones and muscles and enhance metabolism and detoxification. Also, abnormal symptoms of the body and wound can be improved. Glycyrrhetic acid, the most important and potent ingredient of liquorice, has been recorded in Pharmacopoeia of the People’s Republic of China. 18β-Glycyrrhetinic acid is a major metabolite of glycyrrhizin , one of the main constituents of licorice. Both 18β-glycyrrhetinic acid and glycyrrhizin have been shown to exhibit anti-ulcerative, anti-inflammatory, and immunomodulatory properties. 18β-Glycyrrhetinic acid is an inhibitor of the complement pathway (IC50 = 35 μM). At 100 mg/kg/day, 18β-glycyrrhetinic acid is protective against diabetes complications by reducing lipid peroxidation and increasing antioxidant activity in diabetic rats. 18β-Glycyrrhetinic acid inhibits mammalian DNA polymerases α, γ, κ, and λ with IC50 values of 16.1, 19.3, 15.8, and 13.7 μM, respectively. At 100-200 μM, 18β-glycyrrhetinic acid suppresses LPS-induced TNF-α production and NF-κB activation in mouse macrophages.
• Physical properties: Solubility: insoluble in water; it exists in crystal with methanol and chloroform. Melting point: the compound melts at 292–295?°C. Specific optical rotation: under the condition of 20?°C, 589.3?nm, and 1?dm, polarized light rotates at 68° when it passes through the chloroform with a concentration of 64? mol/L.? Both 18α-glycyrrhetic acid and 18β-glycyrrhetic acid are chiral isomers of glycyrrhetic acid.
• Uses: The product may be used as a starting material to prepare 18β-glycyrrhetinic acid derivatives, which show anti-inflammatory and antioxidant properties. An anti-inflammatory (topical). antitussive, antiinflammatory, antibacterial The aglycone of the triterpenoid Glyccyrrhizic acid. glycyrrhetinic acid is anti-irritant, anti-allergenic, anti-inflammatory, skin-lightening, and smoothing properties are attributed to this ingredient, which is also a carrier. It is the organic compound derived from glycyrrhizic acid or shredded licorice roots.
• Indications: Treatment of Addison’s disease, deoxycorticosterone
• Clinical Use: Glycyrrhetic acid has not been applied in clinical treatment till now. Meanwhile, the ramification has come into the market for the property of antiulcer. However, with large doses and long-term usage, the drug gives rise to hypertension, sodium retention, and hypokalemia. When renin-angiotensin-aldosterone system fails to function properly, liquorice-induced pseudoaldosteronism threatens human health .

Technology Process of Enoxolone

There total 35 articles about Enoxolone 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: 90.0%

glycyrrhizin (1405-86-3) → enoxolone (471-53-4)

Guidance literature:

With methanol; thionyl chloride; at 0 - 20 ℃; for 9h; Reagent/catalyst; Inert atmosphere;

DOI:10.1016/j.tet.2017.02.039

Reference yield: 85.0%

glycyrrizhin (83896-44-0,103000-77-7,119479-05-9,142394-43-2,1405-86-3) → enoxolone (471-53-4)

Guidance literature:

With hydrogenchloride; In water;

DOI:10.1016/j.bmcl.2017.11.013

Reference yield: 72.0%

(3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-D-glucopyranosiduronic acid → enoxolone (471-53-4)

Guidance literature:

With hydrogenchloride; In water; acetic acid; at 100 ℃; for 1h;

DOI:10.1039/c7md00210f

upstream raw materials:

acetoxolone

methanol

apioglycyrrhizin

araboglycyrrhizin

Downstream raw materials:

1,2,7-trimethylnaphthalene

18-α-glycyrrhetinic acid

methyl glycyrrhetinate

11-deoxyglycyrrhetinic acid

Refernces

• 1、 Murav'ev, I. A.,Savchenko, L. N.. "STUDY OF KINETICS OF ENZYMATIC HYDROLYSIS OF AMMONIUM GLYCYRRHIZATE". . p. 645 - 647. Retrieved 1985.
• 2、 Sharma, Rajni,Guru, Santosh K.,Jain, Shreyans K.,Pathania, Anup Singh,Vishwakarma, Ram A.,Bhushan, Shashi,Bharate, Sandip B.. "3-(2,6-Dichloro-benzyloxy)-11-oxo-olean-12-ene-29-oic acid, a semisynthetic derivative of glycyrrhetic acid: Synthesis, antiproliferative, apoptotic and anti-angiogenesis activity". . p. 564 - 575. Retrieved 2015.
• 3、 Bag, Braja Gopal,Majumdar, Rakhi. "Self-assembly of a renewable nano-sized triterpenoid 18β-glycyrrhetinic acid". . p. 8623 - 8626. Retrieved 2012.
• 4、 Tschirch,Cederberg. "". . p. 97,100. Retrieved 1907.
• 5、 Shukla, Aparna,Tyagi, Rekha,Meena, Sanjeev,Datta, Dipak,Srivastava, Santosh Kumar,Khan, Feroz. "2D- and 3D-QSAR modelling, molecular docking and in vitro evaluation studies on 18β-glycyrrhetinic acid derivatives against triple-negative breast cancer cell line". . p. 168 - 185. Retrieved 2019/03/07.
• 6、 Kingston, Cian,Wallace, Michael A.,Allentoff, Alban J.,Degruyter, Justine N.,Chen, Jason S.,Gong, Sharon X.,Bonacorsi, Samuel,Baran, Phil S.. "Direct Carbon Isotope Exchange through Decarboxylative Carboxylation". supporting information. p. 774 - 779. Retrieved 2019/01/14.