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G8503

Sigma-Aldrich

18α-Glycyrrhetinic acid

≥95%

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Synonym(s):
18α-Glycyrrhetic acid, 18-Isoglycyrrhetinic acid, 3β-Hydroxy-11-oxo-18α,20β-olean-12-en-29-oic acid
Empirical Formula (Hill Notation):
C30H46O4
CAS Number:
Molecular Weight:
470.68
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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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This Item
PHL82552G10105PHL89694
18α-Glycyrrhetinic acid phyproof® Reference Substance

PHL82552

18α-Glycyrrhetinic acid

18β-Glycyrrhetinic acid phyproof® Reference Substance

PHL89694

18β-Glycyrrhetinic acid

Quality Level

100

Quality Level

-

Quality Level

100

Quality Level

-

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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A simple method for preparation of 18a-glycyrrhetinic acid and its derivatives.
Ignatov DV, et al.
Russian Journal of Bioorganic Chemistry, 29(4), 390-394 (2003)
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
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)
Simultaneous quantification of flavonoids and triterpenoids in licorice using HPLC.
Wang YC and Yang YS.
Journal of Chromatography. B, Biomedical Applications, 850(1), 392-399 (2007)
18a-glycyrrhetinic acid extracted from Glycyrrhiza radix inhibits proliferation and promotes apoptosis of the hepatic stellate cell line.
Zong L, et al.
Journal of Digestive Diseases, 14(6), 328-336 (2013)

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