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50531

Sigma-Aldrich

Glycyrrhizic acid ammonium salt from glycyrrhiza root (licorice)

≥95.0% (NT)

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/REAXYS Number:
3897076
EC Number:
258-887-7
MDL number:
MFCD00167400
UNSPSC Code:
12352106
PubChem Substance ID:
57651257

Quality Level

100

assay

≥95.0% (NT)

optical activity

[α]20/D +48±4°, c = 1% in ethanol: water (1:1)

sweetness

50 × sucrose

impurities

≤7% water

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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Related Categories

Biochem/physiol Actions

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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High mobility group box 1 (HMGB1) participates actively in oxidative stress damage and the latter relates closely to diabetic complications, including poor implant osseointegration. This article is aimed at investigating the effects of HMGB1 on dysfunction of bone marrow stromal
Guannan Li et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 109, 182-190 (2017-08-05)
The potential of licorice dietary supplements to interact with drug metabolism was evaluated by testing extracts of three botanically identified licorice species (Glycyrrhiza glabra L., Glycyrrhiza uralensis Fish. ex DC. and Glycyrrhiza inflata Batalin) and 14 isolated licorice compounds for
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
Zhihui Zhu et al.
PloS one, 9(5), e96576-e96576 (2014-05-08)
The metazoan liver exhibits a remarkable capacity to regenerate lost liver mass without leaving a scar following partial hepatectomy (PH). Whilst previous studies have identified components of several different signaling pathways that are essential for activation of hepatocyte proliferation during
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