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18β-Glycyrrhetinic Acid

Product Name
18β-Glycyrrhetinic Acid
CAS No.
471-53-4
Chemical Name
18β-Glycyrrhetinic Acid
Synonyms
GLYCYRRHETINIC ACID;ENOXOLONE;GLYCYRRHETIC ACID;Glycyrrhetinic;Glycyrrhetinate;biosone;URALENIC ACID;18β-Glycyrrhetic acid;18B-GLYCYRRHETINIC ACID;(2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-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
CBNumber
CB8474793
Molecular Formula
C30H46O4
Formula Weight
470.69
MOL File
471-53-4.mol
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18β-Glycyrrhetinic Acid Property

Melting point:
292-295 °C(lit.)
alpha 
165 º (c=1, CHCl3,on dry ba)
Boiling point:
492.11°C (rough estimate)
Density 
0.9967 (rough estimate)
vapor pressure 
10-220Pa at 20-50℃
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
LogP
4.5 at 20℃
CAS DataBase Reference
471-53-4(CAS DataBase Reference)
EPA Substance Registry System
Enoxolone (471-53-4)
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Safety

Hazard Codes 
Xn
Risk Statements 
22-36
Safety Statements 
22-24/25
WGK Germany 
3
RTECS 
RK0180000
HS Code 
29189900
Toxicity
mouse,LD50,intraperitoneal,308mg/kg (308mg/kg),Drugs in Japan Vol. -, Pg. 319, 1990.
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P330Rinse mouth.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
G10105
Product name
18β-Glycyrrhetinic acid
Purity
97%
Packaging
10g
Price
$117
Updated
2024/03/01
Sigma-Aldrich
Product number
G10105
Product name
18β-Glycyrrhetinic acid
Purity
97%
Packaging
25g
Price
$227
Updated
2024/03/01
TCI Chemical
Product number
G0149
Product name
Glycyrrhetic Acid
Purity
>97.0%(T)
Packaging
1g
Price
$27
Updated
2024/03/01
TCI Chemical
Product number
G0149
Product name
Glycyrrhetic Acid
Purity
>97.0%(T)
Packaging
25g
Price
$192
Updated
2024/03/01
Cayman Chemical
Product number
11845
Product name
β-Glycyrrhetinic Acid
Purity
≥98%
Packaging
1g
Price
$32
Updated
2024/03/01
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18β-Glycyrrhetinic Acid Chemical Properties,Usage,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.

Description

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.

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

The product may be used as a starting material to prepare 18β-glycyrrhetinic acid derivatives, which show anti-inflammatory and antioxidant properties.

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

General Description

18β-Glycyrrhetinic acid is a pentacyclic triterpenoid found in the Glycyrrhiza glabra L.(liquorice) roots. It is the key metabolite of glycyrrhizin and glycyrrhizic acid.

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

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18β-Glycyrrhetinic Acid Suppliers

Youyu County Andyiyuan Biotechnology Co., LTD
Tel
03498026555; 15110806857
Email
747157139@qq.com
Country
China
ProdList
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Shanghai Winherb Medical Technology Co., Ltd.
Tel
400-1865138 13341702378
Fax
QQ:190129269
Email
190129269@qq.com
Country
China
ProdList
1010
Advantage
58
Shanghai Boyle Chemical Co., Ltd.
Tel
021-50182298 021-50180596
Fax
+86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2210
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J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
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Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
4006608290; 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40241
Advantage
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3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15848
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Chembest Research Laboratories Limited
Tel
021-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6013
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TAIYUAN RHF CO.,LTD.
Tel
+86 351 7031519
Fax
+86 351 7031519
Email
sales@RHFChem.com
Country
China
ProdList
2341
Advantage
56
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24539
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81
Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44751
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61
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View Lastest Price from 18β-Glycyrrhetinic Acid manufacturers

Henan Tengmao Chemical Technology Co. LTD
Product
18β-Glycyrrhetinic Acid 471-53-4
Price
US $110.00-90.00/kilogram
Min. Order
1kilogram
Purity
99%
Supply Ability
10 tons/per week
Release date
2024-03-13
Hebei Yanxi Chemical Co., Ltd.
Product
Enoxolone /Glycyrrhetinic Acid 471-53-4
Price
US $360.00/KG
Min. Order
10KG
Purity
98%
Supply Ability
10tons/month
Release date
2020-07-15
Hebei Yanxi Chemical Co., Ltd.
Product
Mexoryl SX;Ecamsule 471-53-4
Price
US $180.00/Kg/Drum
Min. Order
1KG
Purity
99%
Supply Ability
50tons/month
Release date
2020-07-15

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