G10105

Sigma-Aldrich

18β-Glycyrrhetinic acid

97%

Synonym(s):
3β-Hydroxy-11-oxo-18β,20β-olean-12-en-29-oic acid, Enoxolone, Uralenic acid, Glycyrrhetin, Subglycyrrhelinic acid
Empirical Formula (Hill Notation):
C30H46O4
CAS Number:
Molecular Weight:
470.68
Beilstein/REAXYS Number:
2229654
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

optical activity

[α]22/D +170.0°, c = 1 in chloroform

mp

292-295 °C (lit.)

SMILES string

CC1(C)[C@@H](O)CC[C@@]2(C)[C@H]1CC[C@]3(C)[C@@H]2C(=O)C=C4[C@@H]5C[C@](C)(CC[C@]5(C)CC[C@@]34C)C(O)=O

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

InChI key

MPDGHEJMBKOTSU-YKLVYJNSSA-N

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General description

18β-Glycyrrhetinic acid is a pentacyclic triterpenoid found in the Glycyrrhiza glabra L.(liquorice) roots. It is the key metabolite of glycyrrhizin and glycyrrhizic acid.

Application

The product may be used as a starting material to prepare 18β-glycyrrhetinic acid derivatives, which show anti-inflammatory and antioxidant properties.

Packaging

10, 25 g in poly bottle

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Synthesis, anti-inflammatory, and antioxidant activities of 18?-glycyrrhetinic acid derivatives as chemical mediators and xanthine oxidase inhibitors.
Maitraie D, et al.
Bioorganic & Medicinal Chemistry, 17(7), 2785-2792 (2009)
Christian Stanetty et al.
Bioorganic & medicinal chemistry, 18(21), 7522-7541 (2010-09-21)
Glycyrrhetinic acid, the metabolite of the natural product glycyrrhizin, is a well known nonselective inhibitor of 11β-hydroxysteroid dehydrogenase (11β-HSD) type 1 and type 2. Whereas inhibition of 11β-HSD1 is currently under consideration for treatment of metabolic diseases, such as obesity...
From Test Tube to Clinical Trial; Promising Herbs with NF-?B and COX-2 Activity.
Wilkinson F and Cundell DR
Current Immunology Reviews, 10(2), 82-98 (2014)
Gaëlle Le Bras et al.
Journal of medicinal chemistry, 50(24), 6189-6200 (2007-11-06)
Selective hsp90 inhibitors simultaneously destabilize and deplete key signaling proteins involved in cell proliferation and survival, angiogenesis, and metastasis. Investigation of novobiocin analogues lacking the noviose moiety as novel inhibitors of hsp90 was carried out. A novel series of 3-aminocoumarin...
Igor Beseda et al.
Bioorganic & medicinal chemistry, 18(1), 433-454 (2009-11-17)
The effect of glycyrrhetinic acid (GA) and GA-derivatives towards 11beta-hydroxysteroid dehydrogenase (11beta-HSD) was investigated. Novel compounds with modifications at positions C-3, C-11 and C-29 of the GA skeleton were prepared. Single crystal X-ray diffraction data of selected substances are reported...

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