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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
7. Synthesis Route
471-53-4Total: 12 Synthesis Route
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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