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G10105

18β-Glycyrrhetinic acid

Name: 18β-Glycyrrhetinic acid
Brand: ALDRICH

97%

Synonym(s):

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

Empirical Formula (Hill Notation):

C₃₀H₄₆O₄

CAS Number:

471-53-4

Molecular Weight:

470.68

UNSPSC Code:

12352115

NACRES:

NA.22

PubChem Substance ID:

24895033

EC Number:

207-444-6

Beilstein/REAXYS Number:

2229654

MDL number:

MFCD00003706

Assay:

97%

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Properties

Quality Level

100

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)

Description

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.

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Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Synthesis of novel 3-amino and 29-hydroxamic acid derivatives of glycyrrhetinic acid as selective 11β-hydroxysteroid dehydrogenase 2 inhibitors.

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 of glycyrrhetinic acid derivatives for the treatment of metabolic diseases.

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

Synthesis of new glycyrrhetinic acid derived ring A azepanone, 29-urea and 29-hydroxamic acid derivatives as selective 11β-hydroxysteroid dehydrogenase 2 inhibitors.

Rawindra Gaware et al.

Bioorganic & medicinal chemistry, 19(6), 1866-1880 (2011-03-08)

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Global Trade Item Number

SKU	GTIN
G10105-10G	04061833624715
G10105-25G	04061833317693