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Key Documents

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G10105

Sigma-Aldrich

18β-Glycyrrhetinic acid

97%

Sinónimos:

3β-Hydroxy-11-oxo-18β,20β-olean-12-en-29-oic acid, Enoxolone, Glycyrrhetin, Subglycyrrhelinic acid, Uralenic acid

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About This Item

Fórmula empírica (notación de Hill):
C30H46O4
Número de CAS:
471-53-4
Peso molecular:
470.68
Beilstein/REAXYS Number:
2229654
EC Number:
207-444-6
MDL number:
MFCD00003706
UNSPSC Code:
12352115
PubChem Substance ID:
24895033
NACRES:
NA.22

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

Gene Information

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

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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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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
A robust screening method for dietary agents that activate tumour-suppressor microRNAs.
Hagiwara K, et al.
Scientific Reports, 5 (2015)
Rawindra Gaware et al.
Bioorganic & medicinal chemistry, 19(6), 1866-1880 (2011-03-08)
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
18?-Glycyrrhetinic acid interaction with bovine serum albumin.
Zhou N, et al.
Journal of Photochemistry and Photobiology A: Chemistry, 185(2), 271-276 (2007)
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
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