Glycyrrhetinic Acid
Basic information
- CAS
471-53-4- Standard SMILES
CC1(C)[C@@H](O)CC[C@]2(C)[C@H]3C(=O)C=C4[C@@H]5C[C@@](C)(C(=O)O)CC[C@]5(C)CC[C@@]4(C)[C@]3(C)CC[C@@H]12- InChIKey
MPDGHEJMBKOTSU-YKLVYJNSSA-N- Molecular formula
- C30H46O4
- Average molar mass
- 470.7 g/mol
- Monoisotopic mass
- 470.33960994
Overview
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 hydroxy monocarboxylic acid and a cyclic terpene ketone. It is a conjugate acid of a glycyrrhetinate. It derives from a hydride of an oleanane.
Names & identifiers
- Preferred name
- Glycyrrhetinic Acid
- IUPAC
- (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
- English name
- 18β-Glycyrrhetinic Acid
- Molecular formula
- C30H46O4
- Molecular weight
- 470.68
Names & synonyms
enoxolone471-53-4Glycyrrhetic acidGLYCYRRHETINIC ACIDUralenic acid18-beta-Glycyrrhetinic acidJintanRhetinic AcidEnoxolonaEnoxolonum3beta-Hydroxy-11-oxoolean-12-en-30-oic acidDTXSID9020669
Show more names
18B-GLYCYRRHETINIC ACIDGlycyrrhetinateGlycyrrhetinicbiosone18β-Glycyrrhetic acidglycyrrhetin
(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 acidNSC-353473-beta-Hydroxy-11-oxoolean-12-en-30-oic acidP540XA09DROlean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3beta,20beta)-DTXCID50669CHEBI:30853Glyciram
Database identifiers
- CAS
471-53-4- PubChem CID
- 10114
- DTXSID
DTXSID9020669- ChEMBL
CHEMBL230006- ChEBI
Properties
Computed structural properties
- XLogP
- 6.4
- Topological polar surface area
- 74.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 34
- Formal charge
- 0
- Complexity
- 965
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C30 isoprenoids (triterpenes) [PR0106]
Cosmetics
Cosmetic ingredients (Glycyrrhetinic Acid) -> CIR (Cosmetic Ingredient Review)
Skin conditioning
Personal care product -> emollient
Collision Cross Section
223.01 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
213.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 292 · 292-295 °C(lit.)
- alpha
- 165 · 165 º (c=1, CHCl3,on dry ba)
- Boiling point
- 492.11 °C · 492.11°C (rough estimate)
- Density
- 0.9967 · 0.9967 (rough estimate)
- vapor pressure
- 10 · 10-220Pa at 20-50℃
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 35.6% (26 of 73) of reports.
Warning
H302 (64.4%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 73 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3.beta.,20.beta.)-
REACH registered substance: Enoxolone (EC: 207-444-6)
Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3.beta.,20.beta.)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (64.4%)
Toxicology
Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- RK0180000
- hs_code
- 29189900
Chemistry & industry
Pharmacology
ATC Code
D - Dermatologicals
QD - Dermatologicals
MeSH Pharmacological ClassificationSubstances that reduce or suppress INFLAMMATION.
Uses & manufacturing
UsesCIR ingredient: Glycyrrhetinic Acid
Use ClassificationCosmetics -> Skin conditioning
General Manufacturing InformationOlean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3.beta.,20.beta.)-: ACTIVE
Applications
DescriptionExtracting 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.
Description18β-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.
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