Glycyrrhetinic acid
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Glycyrrhetinic acid
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CAS No:
471-53-4
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Formula:
C30H46O4
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Chemical Name:
Glycyrrhetinic acid
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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
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CAS No:
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
470.68400
470.68
215-907-9
P540XA09DR
DTXSID9020669
C526
D - Dermatologicals
2938909030
Characteristics
74.60000
6.41260
white crystalline powder
1.14g/cm3
296 °C
588.3ºC at 760mmHg
323.7ºC
1.563
SOLUBLE IN ACETIC ACID
Store in a cool, dry place. Store in a tightly closed container. Refrigerator (approx 4ºC).
2.71E-16mmHg at 25°C
213.9 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
Safety Information
NONH for all modes of transport
3
R22; R36
S22; S24/25
RK0180000
Xn
Stable under normal temperatures and pressures.
P301 + P312 + P330-P305 + P351 + P338
H302-H319
|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
Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)
12, Po
Glycyrrhetinic acid Use and Manufacturing
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.
Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3.beta.,20.beta.)-: ACTIVE
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
Drug Function and Efficacy
Possesses anti-inflammatory, anti-allergic and antipruritic effects similar to those of adrenocortical hormones
Registered Holders
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Qingdao Keyuan Huigu Biopharmaceutical Co., Ltd.
Active
China
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XinjiangTianshan Pharmaceutical Ind. Co., Ltd.
Active
China
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Shaanxi Fujie Pharmaceutical Co., Ltd.
Active
China
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