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Glycyrrhetinic acid

Glycyrrhetinic acid structure

CAS No:
471-53-4
Formula:
C30H46O4
Chemical Name:
Glycyrrhetinic acid
Synonyms:
Olean-12-en-29-oic acid,3-hydroxy-11-oxo-,(3β,20β)-;Olean-12-en-30-oic acid,3β-hydroxy-11-oxo-;Uralenic acid;(3β,20β)-3-Hydroxy-11-oxoolean-12-en-29-oic acid;Glycyrrhetic acid;18β-Glycyrrhetic acid;Glycyrrhetinic acid;18β-Glycyrrhetinic acid;α-Glycyrrhetinic acid;Biosone;Enoxolone;Glycyrrhetin;Subglycyrrhelinic acid;GM 1658;STX 352;Arthrodont;PO 12;NSC 35347;8055-71-8;15301-63-0;107420-91-7;202522-39-2;299198-00-8;2088830-40-2;2442477-01-0
Categories:
Cosmetic Ingredient > Skin Conditioning

Description

18β-Glycyrrhetinic acid is the major bioactive component of Glycyrrhizae Radix and possesses anti-ulcerative, anti-inflammatory and antiproliferative properties.

Glycyrrhetinic acid is 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. It has a role as an immunomodulator and a plant metabolite. It is a pentacyclic triterpenoid, a cyclic terpene ketone and a hydroxy monocarboxylic acid. It is a conjugate acid of a glycyrrhetinate. It derives from a hydride of an oleanane.|Enoxolone (glycyrrhetic acid) has been investigated for the basic science of Apparent Mineralocorticoid Excess (AME).|Enoxolone is a pentacyclic triterpenoid aglycone metabolite of glycyrrhizin, which is a product of the plant Glycyrrhiza glabra (licorice), with potential expectorant, and gastrokinetic activities. After administration, enoxolone inhibits the metabolism of prostaglandins by both 15-hydroxyprostaglandin dehydrogenase [NAD(+)] and prostaglandin reductase 2. Therefore, this agent potentiates the activity of prostaglandin E2 and F2alpha, which inhibits gastric secretion while stimulating pancreatic secretion and the secretion of intestinal and respiratory mucus, leading to increased intestinal motility and antitussive effects. Additionally, this agent inhibits 11 beta-hydroxysteroid dehydrogenase and other enzymes involved in the conversion of cortisol to cortisone in the kidneys.|An oleanolic acid from GLYCYRRHIZA that has some antiallergic, antibacterial, and antiviral properties. It is used topically for allergic or infectious skin inflammation and orally for its aldosterone effects in electrolyte regulation.

Glycyrrhetinic acid Basic Attributes

Molecular Weight：

470.68400

Exact Mass：

470.68

EC Number：

215-907-9

UNII：

P540XA09DR

DSSTox ID：

DTXSID9020669

NCI Thesaurus Code：

C526

ATC Code：

D - Dermatologicals

HScode：

2938909030

Characteristics

PSA：

74.60000

XLogP3：

6.41260

Appearance：

white crystalline powder

Density：

1.14g/cm3

Melting Point：

296 °C

Boiling Point：

588.3ºC at 760mmHg

Flash Point：

323.7ºC

Refractive Index：

1.563

Water Solubility：

SOLUBLE IN ACETIC ACID

Storage Conditions：

Store in a cool, dry place. Store in a tightly closed container. Refrigerator (approx 4ºC).

Vapor Pressure：

2.71E-16mmHg at 25°C

Collision Cross Section：

213.9 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R22; R36

safety instructions：

S22; S24/25

RTECS Number：

RK0180000

Marks：

Stability/Shelf Life：

Stable under normal temperatures and pressures.

Precautionary statement(s)：

P301 + P312 + P330-P305 + P351 + P338

Hazard Statements：

H302-H319

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 40 companies from 1 notifications to the ECHA C&L Inventory.|P264, P270, P280, P301+P312, P305+P351+P338, P330, P337+P313, and P501|Aggregated GHS information provided by 67 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)

MeSH Entry Terms：

12, Po

Glycyrrhetinic acid Use and Manufacturing

Uses

Expectorant and antitussive. Sweeteners; sweet taste modifiers; flavoring agents (used in conjunction with table salt, particularly effective); flavor enhancers (dairy products, cocoa products, egg products, mutton, etc.). Our folks are used to sauces, sauce products, pickles, etc. Antibiotic drugs, used to treat infections of Staphylococcus, Streptococcus, Escherichia coli, Helicobacter, etc.; It is an important raw material for medicine and high-end cosmetics, with anti-inflammatory and anti-allergic effects, inhibiting bacterial reproduction, etc.; This product is an anti-inflammatory drug . It is used to treat diseases such as adrenal hypofunction, gastric and duodenal ulcers.

Manufacturing Info：

Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3.beta.,20.beta.)-: ACTIVE

Use Classification：

Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C30 isoprenoids (triterpenes) [PR0106]|Cosmetics -> Skin conditioning

Computed Properties

Molecular Weight:470.7
XLogP3:6.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:470.33960994
Monoisotopic Mass:470.33960994
Topological Polar Surface Area:74.6
Heavy Atom Count:34
Complexity:965
Defined Atom Stereocenter Count:9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Ethanol

Methanol

Drug Function and Efficacy

Possesses anti-inflammatory, anti-allergic and antipruritic effects similar to those of adrenocortical hormones

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Glycyrrhetinic acid
Specifications	API
Manufacturer	XinjiangTianshan Pharmaceutical Ind. Co., Ltd.

Compound Crotamiton Cream
Ingredients	This product is a compound preparation, and its components are: each gram (g) contains 50 mg of crotamiton, 10 mg of diphenhydramine, 5 mg of vitamin E, and 2 mg of glycyrrhetinic acid.
Indication	Drug interactions may occur if used with other drugs. Please consult your doctor or pharmacist for details.
Specifications	15g/stick
Manufacturer	Mentholatum (CHINA) Pharmaceuticals Limited

Compound camphor cream
Ingredients	This product is a compound preparation, whose components are: camphor 4%, menthol 3%, methyl salicylate 2%, diphenhydramine 1%, chlorhexidine gluconate 0.2%, and glycyrrhetinic acid 0.3%.
Indication	If you are using other medicines, you should consult your physician or pharmacist before using this product.
Specifications	30g
Manufacturer	Heilongjiang Tianlong Pharmaceutical Co., Ltd.

See More Related Drugs

Registered Holders

Qingdao Keyuan Huigu Biopharmaceutical Co., Ltd.

China
Active
XinjiangTianshan Pharmaceutical Ind. Co., Ltd.

China
Active
Shaanxi Fujie Pharmaceutical Co., Ltd.

China
Active

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18β-Glycyrrhetinic Acid, CAS:471-53-4

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Guide of Glycyrrhetinic acid

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
Material
Drug Function and Efficacy
Related Drugs
Registered Holders
Recommended Suppliers
Learn More Other Chemicals

Glycyrrhetinic acid

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