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18β-Glycyrrhetinic Acid

18β-Glycyrrhetinic Acid
18β-Glycyrrhetinic Acid structure
CAS No.
471-53-4
Chemical Name:
18β-Glycyrrhetinic Acid
Synonyms
PO 12;18 BETA;GM 1658;STX 352;biosone;ENOXOLONE;ENOLOXONE;NSC 35347;Arthrodont;glycyrrhetin
CBNumber:
CB8474793
Molecular Formula:
C30H46O4
Formula Weight:
470.69
MOL File:
471-53-4.mol

18β-Glycyrrhetinic Acid Properties

Melting point:
292-295 °C(lit.)
Boiling point:
492.11°C (rough estimate)
alpha 
165 º (c=1, CHCl3,on dry ba)
Density 
0.9967 (rough estimate)
refractive index 
162 ° (C=1, MeOH)
storage temp. 
2-8°C
solubility 
Practically insoluble in water, soluble in ethanol, sparingly soluble in methylene chloride.
pka
pKa 5.56±0.1 (Uncertain)
form 
Crystalline Powder
color 
White to off-white
optical activity
[α]22/D +170.0°, c = 1 in chloroform
Water Solubility 
SOLUBLE IN ACETIC ACID
Merck 
14,3590
BRN 
2229654
CAS DataBase Reference
471-53-4(CAS DataBase Reference)
EWG's Food Scores
1
FDA UNII
P540XA09DR
EPA Substance Registry System
Enoxolone (471-53-4)
SAFETY
  • Risk and Safety Statements
Hazard Codes  Xn
Risk Statements  22-36
Safety Statements  22-24/25
WGK Germany  3
RTECS  RK0180000
HS Code  29189900
NFPA 704
0
1 0

18β-Glycyrrhetinic Acid price More Price(9)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich G10105 18β-Glycyrrhetinic acid 97% 471-53-4 10g $96.6 2021-03-22 Buy
Sigma-Aldrich E0180500 Enoxolone European Pharmacopoeia (EP) Reference Standard 471-53-4 $190 2021-03-22 Buy
Sigma-Aldrich G10105 18β-Glycyrrhetinic acid 97% 471-53-4 25g $215 2021-03-22 Buy
TCI Chemical G0149 Glycyrrhetic Acid >97.0%(T) 471-53-4 1g $23 2021-03-22 Buy
TCI Chemical G0149 Glycyrrhetic Acid >97.0%(T) 471-53-4 25g $168 2021-03-22 Buy

18β-Glycyrrhetinic Acid Chemical Properties,Uses,Production

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.

Chemical Properties

white or greyish-white crystalline powder

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.

History

Glycyrrhetic acid originates from hydrolysis of glycyrrhizin, which has a therapeutic effect on disease. Dating back to the 1930s, the chemical structure of glycyrrhetic acid was demonstrated . Subsequently, the discovery of antiulcer activity promotes following research . The ramification of glycyrrhetic acid, carbenoxolone sodium, has a therapeutic effect on ulcer. In 2010, followed by the approval of raw materials, batches of tablets and capsules were approved in 2009, respectively. In foreign countries, 18β-glycyrrhetic acid was studied for anti-inflammatory effect on arthritis, rheumatoid disease, and periodontitis in BioNetWorks. The company applied for the patent of 18β-glycyrrhetic acid in 1999. Also, after joining the leading worldwide market in 2006, phase III clinical trials would be carried out in 2007. However, the progress was hindered in 2008. To detecting more indications, its carbenoxolone sodium was studied by other three companies: after conducting phase III clinical trials in the UK, the project of RB intending to improve nonspecific inflammatory bowel disease was given up in 1992. York Pharma expected to make progress in psoriasis with gel or cream; however, the project has been in a standstill after phase II clinical trials was conducted from 2005 to 2009. Canada pharmaceutical company, Oxalys Pharmaceuticals, research it for treating Huntington’s disease, and it was included in the orphan drug list by the USA in 2014. Till now, phase I clinical trials are still continuing.

Uses

An anti-inflammatory (topical).

Uses

antitussive, antiinflammatory, antibacterial

Uses

The aglycone of the triterpenoid Glyccyrrhizic acid.

Uses

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.

Definition

ChEBI: A pentacyclic triterpenoid that is olean-12-ene substituted by a hydroxy group at position 3, an oxo group at position 11 and a carboxy group at position 30.

Indications

Treatment of Addison’s disease, deoxycorticosterone

Pharmacology

Thirty percent of glycyrrhetinic acid can be effectively used by the body; both 18α-glycyrrhetic acid and 18β-glycyrrhetic acid reduce by half in 2.24 h and 11.5 h separately. CYP3A promotes metabolism with hydroxyl added to 22α and 24α .There are lots of pharmacological activities : it plays an anti-inflammatory role by inhibiting the activity of phospholipase A2 and lipoxygenase to reduce mediators of inflammation; the compound promotes antiulcer activity through the production of more PGE2 and secretion of gastric mucus; it also provokes proliferation of gastric cell to protect the mucosa from ulceration. The complex which consists of glycyrrhetinic acid and carotenoid plays antioxidation by scavenging free radical. Glycyrrhetinic acid inhibits the replication of viral DNA to achieve an antiviral effect at the concentration of 4×10?5 mol/L; it also inhibits proliferation of tumor cell and promotes apoptosis and differentiation. The decreasing ability of invasion exerts an antitumor effect. Glycyrrhetinic acid is considered to have extensive antiarrhythmic effects through inhibition of L-type calcium channel. In addition, glycyrrhetinic acid functions as an anticholinesterase (1.7×10?5 mol/L), anticoagulant, and antitetanus toxin; it also improves inner ear hearing (100 mg/kg, intramuscular injection) and improves absorption of insulin.

Anticancer Research

Glycyrrhetinic acid in combinationwith etoposide inhibits thetopoisomerase 2α and inducesapoptosis
Cai et al.(2017)

Anticancer Research

It was reported that GA at noncytotoxic concentrationshowed synergistic effect in combination with anticancer drug, etoposide (VP-16).Specifically, GA enhanced cytotoxicity through regulating topoisomerase II-αtargeted by etoposide. Also, GA sensitized the cells to etoposide through elevatingtopoisomerase II-α with a 2.4-fold rate at 12 h time point. From 12 to 48 h, GAhalved the expression of topoisomerase II-α and stimulated apoptosis, whichexhibited its antineoplastic effect. They reported that GA was more potentiallyeliminating the TNBC cells when compared with Glycyrrhizin Acid (Cai et al. 2017).

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 .

18β-Glycyrrhetinic Acid Preparation Products And Raw materials

Raw materials

Preparation Products


18β-Glycyrrhetinic Acid Suppliers

Global( 429)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
SINOPRO.CO.LTD
0082-42-721-7177
0082-42-3676760 michael@sinopro.co.kr South Korea 300 58
Henan DaKen Chemical CO.,LTD.
+86-371-66670886
info@dakenchem.com China 21022 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Shanghai Time Chemicals CO., Ltd.
+8618017249410 +86-021-57951555
+86-021-57951555 jack.li@time-chemicals.com CHINA 1365 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 8882 55
Shanghai Zheyan Biotech Co., Ltd.
18017610038
zheyansh@163.com CHINA 3623 58
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29958 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD
+86 18953170293
+86 0531-67809011 sales@sdzschem.com CHINA 2858 58
Chengdu Biopurify Phytochemicals Ltd.
18482058008 18080483897
maggie@biopurify.com CHINA 2712 58
Nanjing Dolon Biotechnology Co.,Ltd.
18905173768
sales@dolonchem.com CHINA 2972 58

View Lastest Price from 18β-Glycyrrhetinic Acid manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-10-14 Enoxolone /Glycyrrhetinic Acid
471-53-4
US $360.00 / KG 10KG 98% 10tons/month Hebei Dongdu Import and Export Co. LTD
2021-08-26 Glycyrrhetinic Acid
471-53-4
US $5.70 / Kg/Bag 10g 99.9% 10000kg Hebei Crovell Biotech Co Ltd
2021-07-13 Mexoryl SX;Ecamsule
471-53-4
US $180.00 / Kg/Drum 1KG 99% 50tons/month Hebei Yanxi Chemical Co., Ltd.

18β-Glycyrrhetinic Acid Spectrum


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