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G2137

Sigma-Aldrich

Glycyrrhizic acid ammonium salt from glycyrrhiza root (licorice)

≥70% (HPLC)

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Synonym(s):
3-O-(2-O-β-D-Glucopyranuronosyl-α-D-glucopyranuronosyl)-18β-glycyrrhetinic acid ammonium salt, Glycyrrhizin
Linear Formula:
C42H62O16 · NH3
CAS Number:
Molecular Weight:
839.96
Beilstein:
3897076
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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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This Item
50531PHL82467G0460000
Glycyrrhizin ammonium salt phyproof® Reference Substance

PHL82467

Glycyrrhizin ammonium salt

Glycyrrhizate monoammonium European Pharmacopoeia (EP) Reference Standard

G0460000

Glycyrrhizate monoammonium

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

-

Quality Level

200

Quality Level

100

Quality Level

-

Quality Level

-

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

Signal Word

Warning

Hazard Statements

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

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Glycyrrhizate monoammonium European Pharmacopoeia (EP) Reference Standard

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18α-Glycyrrhetinic acid phyproof® Reference Substance

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Sigma-Aldrich

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Hong Fan et al.
Journal of neuroinflammation, 17(1), 295-295 (2020-10-11)
Spinal cord injury (SCI) favors a persistent pro-inflammatory macrophages/microglia-mediated response with only a transient appearance of anti-inflammatory phenotype of immune cells. However, the mechanisms controlling this special sterile inflammation after SCI are still not fully elucidated. It is known that
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

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