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G10105

Sigma-Aldrich

18β-Glycyrrhetinic acid

97%

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Synonym(s):
3β-Hydroxy-11-oxo-18β,20β-olean-12-en-29-oic acid, Enoxolone, Glycyrrhetin, Subglycyrrhelinic acid, Uralenic acid
Empirical Formula (Hill Notation):
C30H46O4
CAS Number:
Molecular Weight:
470.68
Beilstein:
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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1 of 4

This Item
L6250M6699E0180500
Lithocholic acid ≥95%

Sigma-Aldrich

L6250

Lithocholic acid

Maslinic acid ≥98% (HPLC)

Sigma-Aldrich

M6699

Maslinic acid

Enoxolone European Pharmacopoeia (EP) Reference Standard

E0180500

Enoxolone

mp

292-295 °C (lit.)

mp

183-188 °C (lit.)

mp

-

mp

292-295 °C (lit.)

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

-

optical activity

[α]22/D +170.0°, c = 1 in chloroform

optical activity

-

optical activity

-

optical activity

-

Gene Information

human ... HSD11B1(3290), HSD11B2(3291)
rat ... Hsd11b1(25116), Hsd11b2(25117)

Gene Information

human ... POLA1(5422), TOP2A(7153)
rat ... Polb(29240)

Gene Information

-

Gene Information

-

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Ammonium glycyrrhizate European Pharmacopoeia (EP) Reference Standard

Y0000433

Ammonium glycyrrhizate

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
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)
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
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)
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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