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Merck
CN

G10105

18β-Glycyrrhetinic acid

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%

Key Documents

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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)

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Related Categories

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

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM2783
BCCJ1409
BCCF7969
BCCD0167
BCCC0217

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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
18?-Glycyrrhetinic acid interaction with bovine serum albumin.
Zhou N, et al.
Journal of Photochemistry and Photobiology A: Chemistry, 185(2), 271-276 (2007)
A robust screening method for dietary agents that activate tumour-suppressor microRNAs.
Hagiwara K, et al.
Scientific Reports, 5 (2015)
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Global Trade Item Number

SKUGTIN
G10105-10G04061833624715
G10105-25G04061833317693

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