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G2137

Sigma-Aldrich

Glycyrrhizic acid ammonium salt from glycyrrhiza root (licorice)

≥70% (HPLC)

Synonym(s):

3-O-(2-O-β-D-Glucopyranuronosyl-α-D-glucopyranuronosyl)-18β-glycyrrhetinic acid ammonium salt, Glycyrrhizin

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About This Item

Linear Formula:
C42H62O16 · NH3
CAS Number:
53956-04-0
Molecular Weight:
839.96
Beilstein:
3897076
EC Number:
258-887-7
MDL number:
MFCD00167400
UNSPSC Code:
12352005
PubChem Substance ID:
57654204
NACRES:
NA.22

Assay

≥70% (HPLC)

storage temp.

2-8°C

SMILES string

N.CC1(C)[C@H](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)O[C@H]6O[C@@H]([C@@H](O)[C@H](O)[C@H]6O[C@@H]7O[C@@H]([C@@H](O)[C@H](O)[C@H]7O)C(O)=O)C(O)=O

InChI

1S/C42H62O16.H3N/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50;/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54);1H3/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+;/m0./s1

InChI key

ILRKKHJEINIICQ-OOFFSTKBSA-N

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General description

Glycyrrhizic acid (GA) is a non-selective inhibitor of 11β-hydroxysteroid dehydrogenase (11β-HSD), which mediates the inter-conversion of active and inactive glucocorticoids. GA also shows inhibitory effect on the cytokine activity of high-mobility group box 1 protein (HMGB1).

Application

The product has been used a source of glycyrrhizic acid (GA), to study its effect on glucose intolerance and insulin resistance in rats fed on high-fat/high-sucrose (HF/HS) diet.

Biochem/physiol Actions

Biologically active constituent in the sweet root of Glycyrrhiza species (licorice). Antiviral.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ashraf M Morgan et al.
Environmental science and pollution research international, 26(34), 34924-34930 (2019-10-30)
Atrazine (ATR) is a common herbicide used worldwide. It is a potent endocrine disruptor that causes hormonal imbalance. We investigated the modulatory role predisposed by glycyrrhizic acid (GA) against the hazardous effects caused by the ATR in the rabbit spleen.
Novel inhibitory effects of Glycyrrhizic Acid on the accumulation of advanced glycation end product and its receptor expression.
Cheng HS, et al.
Natural products and bioprospecting, 4(6), 325-333 (2014)
High-mobility group box-1 was released actively and involved in LPS induced depressive-like behavior.
Wu TY, et al.
Journal of Psychiatric Research, 64, 99-106 (2015)
Oluwaseun O Ojo et al.
American journal of physiology. Lung cellular and molecular physiology, 309(11), L1354-L1366 (2015-10-04)
High mobility group box 1 (HMGB1) is a damage-associated molecular pattern (DAMP) protein that binds Toll-like receptors (e.g., TLR4) and the receptor for advanced glycated end products (RAGE). The direct effects of HMGB1 on airway structural cells are not fully
Yu Okuma et al.
Neuropharmacology, 85, 18-26 (2014-05-27)
Glycyrrhizin (GL) is a major constituent of licorice root and has been suggested to inhibit the release of high mobility group box-1 (HMGB1), a protein considered representative of damage-associated molecular patterns. We found that GL bound HMGB1 but not RAGE
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