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Home> Encyclopedia >Forest chemicals>Antioxidants>Pharmaceutical Intermediates
18β-Glycyrrhetinic Acid structure
18β-Glycyrrhetinic Acid structure

18β-Glycyrrhetinic Acid

Iupac Name:(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
CAS No.: 471-53-4
Molecular Weight:470.694
Modify Date.: 2023-02-09 13:27
Introduction:

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.

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1. Names and Identifiers
1.1 Name
18β-Glycyrrhetinic Acid
1.2 Synonyms

(11α)-21-Fluoro-11,17-dihydroxypregn-4-ene-3,20-dione (20S)-3β-Hydroxy-11-oxo-5α-olean-12-en-29-oic acid (3β,20β)-3-Hydroxy-11-oxoolean-12-en-29-oic acid 18-beta-glycyrrheticacid 18β-Glycyrrhetic acid Aloe Vera, Freeze Dried Powder Arthrodont Biosone Enoxolone Enoxolone, 3β-Hydroxy-11-oxo-18β,20β-olean-12-en-29-oic acid Glycyrrhetic acid Glycyrrhetin Glycyrrhetinic acid GLYCYRRHETINIC ACID, 18B-(P) GLYCYRRHETINIC ACID, 18B-(SH) GM 1658 NSC 35347 Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3b,20b)- Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3β,20β)- Olean-12-en-30-oic acid, 3β-hydroxy-11-oxo- PO 12 Pregn-4-ene-3,20-dione, 21-fluoro-11,17-dihydroxy-, (11α)- STX 352 Subglycyrrhelinic acid Uralenic acid α-Glycyrrhetinic acid

1.3 CAS No.
471-53-4
1.4 CID
10114
1.5 EINECS(EC#)
207-444-6; 215-907-9
1.6 Molecular Formula
C30H46O4 (isomer)
1.7 Inchi
InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1
1.8 InChkey
MPDGHEJMBKOTSU-YKLVYJNSSA-N
1.9 Canonical Smiles
CC1(C2CCC3(C(C2(CCC1O)C)C(=O)C=C4C3(CCC5(C4CC(CC5)(C)C(=O)O)C)C)C)C
1.10 Isomers Smiles
C[C@]12CC[C@](C[C@H]1C3=CC(=O)[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)(C)C(=O)O
2. Properties
2.1 Density
1.14
2.1 Melting point
292 - 295 C
2.1 Boiling point
588.3°Cat760mmHg
2.1 Refractive index
162 ° (C=1, MeOH)
2.1 Flash Point
323.7°C
2.1 Precise Quality
470.34000
2.1 PSA
74.60000
2.1 logP
6.41260
2.1 Appearance
white crystalline powder
2.2 Chemical Properties
white or greyish-white crystalline powder
2.3 Color/Form
Powder
2.4 pKa
pKa 5.56±0.1 (Uncertain)
2.5 Water Solubility
SOLUBLE IN ACETIC ACID
2.6 Stability
Stable under normal temperatures and pressures.
2.7 StorageTemp
Store in a cool, dry place. Store in a tightly closed container. Refrigerator (approx 4 C).
3. Use and Manufacturing
3.1 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.
3.2 GHS Classification
Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 25 companies from 1 notifications to the ECHA C&L Inventory.

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P264, P270, P301+P312, P330, and P501
3.3 Usage
An anti-inflammatory (topical).
4. Safety and Handling
4.1 Hazard Codes
Xn
4.1 Risk Statements
R22;R36
4.1 Safety Statements
22-24/25
4.1 Hazard Declaration
H302-H319
4.1 RIDADR
HAZARD
4.1 Caution Statement
P301 + P312 + P330-P305 + P351 + P338
4.1 WGK Germany
3
4.1 RTECS
RK0180000
4.1 Safety
Poison by intravenous and intraperitoneal routes. When heated to decomposition it emits acrid smoke and irritating fumes.
4.2 Specification

white or greyish-white crystalline powder
usageEng:An anti-inflammatory (topical).
Safety Statements:22-24/25
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
4.3 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RK0180000
CHEMICAL NAME :
Olean-12-en-30-oic acid, 3-beta-hydroxy-11-oxo-
CAS REGISTRY NUMBER :
471-53-4
BEILSTEIN REFERENCE NO. :
2229654
LAST UPDATED :
199701
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C30-H46-O4
MOLECULAR WEIGHT :
470.76
WISWESSER LINE NOTATION :
L F6 E6 B666 CV DUTJ A1 HVQ H1 K1 N1 O1 S1 S1 TQ -ALPHA

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
308 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,319,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
56 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#02067
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H302 Harmful if swallowed

H319 Causes serious eye irritation

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Merck
14,3590
9.1 Chemical Properties
white or greyish-white crystalline powder
9.2 Uses
An anti-inflammatory (topical).
9.3 Uses
antitussive, antiinflammatory, antibacterial
9.4 Uses
The aglycone of the triterpenoid Glyccyrrhizic acid.
9.5 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.
9.6 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.
9.7 Collision Cross Section
213.9 ?2 [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
9.8 Mesh
Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)
9.9 Mesh Entry Terms
12, Po
9.10 Manufacturing Info
Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3.beta.,20.beta.)-: ACTIVE
9.11 Use Classification
Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C30 isoprenoids (triterpenes) [PR0106]|Cosmetics -> Skin conditioning
10. Computational chemical data
  • Molecular Weight: 470.694g/mol
  • Molecular Formula: C30H46O4
  • Compound Is Canonicalized: True
  • XLogP3-AA: 6.4
  • Exact Mass: 470.33960994
  • Monoisotopic Mass: 470.33960994
  • Complexity: 965
  • Rotatable Bond Count: 1
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Topological Polar Surface Area: 74.6
  • Heavy Atom Count: 34
  • Defined Atom Stereocenter Count: 9
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADcfB4OAAAAAAAAAAAAAAAAAAAAAAAAAAwYMGCAAAAAADAAAAAGgAACAAADxSggAICCAAAAgCIAqDSCAAAAAAgAAAACAEAAEgAEBIAAQAAQAAEgAAIAQOIyPCPgAAAAAAAAADAAAYAADAAAAAAAAAAAA==
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