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Merck

G8503

Sigma-Aldrich

18α-Glycyrrhetinic acid

≥95%

Sinónimos:

18α-Glycyrrhetic acid, 18-Isoglycyrrhetinic acid, 3β-Hydroxy-11-oxo-18α,20β-olean-12-en-29-oic acid

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About This Item

Fórmula empírica (notación de Hill):
C30H46O4
Número de CAS:
Peso molecular:
470.68
EC Number:
MDL number:
UNSPSC Code:
12352115
PubChem Substance ID:
NACRES:
NA.22

assay

≥95%

SMILES string

[H][C@]12C[C@](C)(CC[C@]1(C)CC[C@]3(C)C2=CC(=O)C4[C@@]5(C)CC[C@H](O)C(C)(C)[C@]5([H])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-/m1/s1

InChI key

MPDGHEJMBKOTSU-PMTKVOBESA-N

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General description

18α-Glycyrrhetinic acid (18α-GA) is a bioactive triterpenoid found in licorice. It shows selective inhibition of 11-HSD1 (11-hydroxysteroid dehydrogenase 1). It also shows anti-proliferative and apoptotic effect on hepatic stellate cells (HSCs).

Application

18α-Glycyrrhetinic acid may be used to synthesize:
  • 3-keto-18α-glycyrrhetinic acid
  • methyl esters of 18α-glycyrrhetinic acid
  • methyl esters of 3-keto-18α-glycyrrhetinic acid

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificados de análisis (COA)

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Selective inhibition of 11?-hydroxysteroid dehydrogenase 1 by 18a-glycyrrhetinic acid but not 18?-glycyrrhetinic acid.
Classen-Houben D, et al.
The Journal of Steroid Biochemistry and Molecular Biology, 113(3), 248-252 (2009)
Sebastian M Goerke et al.
Tissue engineering. Part A, 18(23-24), 2395-2405 (2012-06-27)
Neovascularization represents an important issue in tissue-engineering applications, since survival of implanted cells strongly relies on sufficient oxygen and nutrient supply. We have recently observed that human bone marrow-derived mesenchymal stem cells (MSCs) support neovessel formation originating from coimplanted endothelial
Mohammad Shahidullah et al.
American journal of physiology. Cell physiology, 302(12), C1751-C1761 (2012-04-12)
In several tissues, transient receptor potential vanilloid 4 (TRPV4) channels are involved in the response to hyposmotic challenge. Here we report TRPV4 protein in porcine lens epithelium and show that TRPV4 activation is an important step in the response of
Manuel Viotti et al.
PLoS biology, 10(3), e1001276-e1001276 (2012-03-14)
Establishment of left-right (LR) asymmetry occurs after gastrulation commences and utilizes a conserved cascade of events. In the mouse, LR symmetry is broken at a midline structure, the node, and involves signal relay to the lateral plate, where it results
Manuela Buonanno et al.
PloS one, 6(6), e21540-e21540 (2011-07-09)
An increased risk of carcinogenesis caused by exposure to space radiation during prolonged space travel is a limiting factor for human space exploration. Typically, astronauts are exposed to low fluences of ionizing particles that target only a few cells in

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