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G10105

Sigma-Aldrich

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:
Molecular Weight:
470.68
Beilstein:
2229654
EC Number:
MDL number:
UNSPSC Code:
12352115
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.

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

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