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G9548

Sigma-Aldrich

Glabridin

≥98% (HPLC), powder, isoflavan

Synonyma:

4-[(3R)-3,4-Dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-3-yl]-1,3-benzenediol, Glabridin, (R)-4-(3,4-Dihydro-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b′]dipyran-3-yl)-1,3-benzenediol

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About This Item

Empirický vzorec (Hillův zápis):
C20H20O4
Číslo CAS:
59870-68-7
Molekulová hmotnost:
324.37
Beilstein/REAXYS Number:
7141956
MDL number:
MFCD03427694
UNSPSC Code:
12352200
PubChem Substance ID:
329799990
NACRES:
NA.77

Název produktu

Glabridin, ≥98% (HPLC), powder

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to light brown

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

room temp

SMILES string

CC1(C)Oc2ccc3C[C@@H](COc3c2C=C1)c4ccc(O)cc4O

InChI

1S/C20H20O4/c1-20(2)8-7-16-18(24-20)6-3-12-9-13(11-23-19(12)16)15-5-4-14(21)10-17(15)22/h3-8,10,13,21-22H,9,11H2,1-2H3/t13-/m0/s1

InChI key

LBQIJVLKGVZRIW-ZDUSSCGKSA-N

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Application

Glabridin has been used:
  • to analyze its transthyretin (TTR)-stabilizing effect in plasma of healthy volunteers
  • as a standard in proton nuclear magnetic resonance (1H NMR) to study the interaction between glabridin and human serum albumin using multi-spectroscopic and molecular docking techniques
  • to study its effect on nucleotide-binding oligomerization domain-like receptor pyrin-domain-containing protein 3 (NLRP3) inflammasome activation

Biochem/physiol Actions

Glabridin is a bio-available isoflavan isolated from licorice (Glycyrrhiza glabra L.) root extract. Glabridin has been reported to possess various biological activities including strong antioxidant activity, antioxidant against LDL oxidation, anti-Helicobacter pylori properties, estrogen-like activity and antinephritic and radical scavenging activities. Also it appears to inhibit serotonin re-uptake, melanogenesis, inflammation and cytochrome P450 3A4, 2B6, and 2C9.
Glabridin is a main component of glavonoid, also known as licorice-derived flavonoid oil, which is a natural supplement used in traditional medicine and herbal medicine.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

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Osvědčení o analýze (COA)

Lot/Batch Number
0000399060
0000406059
0000399061
0000376147
0000184149

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Glycyrrhizic Acid Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1516

Glycyrrhizic Acid

Glycyrrhizic acid United States Pharmacopeia (USP) Reference Standard

USP

1295888

Glycyrrhizic acid

Glycyrrhizic acid ammonium salt from glycyrrhiza root (licorice) ≥95.0% (NT)

Sigma-Aldrich

50531

Glycyrrhizic acid ammonium salt from glycyrrhiza root (licorice)

Bacoside A3 analytical standard

Supelco

53889

Bacoside A3

Glycyrrhizin phyproof® Reference Substance

PHL89217

Glycyrrhizin

18β-Glycyrrhetinic acid 97%

Sigma-Aldrich

G10105

18β-Glycyrrhetinic acid

Baicalein 98%

Sigma-Aldrich

465119

Baicalein

Silibinin ≥98% (HPLC)

Sigma-Aldrich

S0417

Silibinin

Polycaprolactone average Mn 45,000

Sigma-Aldrich

704105

Polycaprolactone

Structural insights into the binding behavior of isoflavonoid glabridin with human serum albumin
Razzak MA, et al.
Food Hydrocolloids, 91, 290-300 (2019)
Fumiki Aoki et al.
Journal of the American College of Nutrition, 26(3), 209-218 (2007-07-20)
Licorice flavonoids have various physiological activities such as abdominal fat-lowering, hypoglycemic and antioxidant effects. Licorice flavonoid oil (LFO: Kaneka Glavonoid Rich Oil) is a new dietary ingredient containing licorice flavonoids dissolved in medium-chain triglycerides (MCT). Glabridin is one of the
Hiroaki Matsushita et al.
Heliyon, 7(10), e08101-e08101 (2021-10-26)
Transthyretin (TTR) is an amyloidogenic protein associated with hereditary and nonhereditary transthyretin amyloidoses (ATTR). Dissociation of the tetramer of TTR to the monomer induces TTR misfolding, which leads to amyloid fibril formation and triggers the onset of ATTR amyloidosis. Stabilizers
A novel fluorescent recombinant cell-based biosensor for screening NLRP3 inflammasome inhibitors
Ye Y, et al.
Sensors and Actuators B, Chemical, 301, 126864-126864 (2019)
Rudy Simons et al.
Analytical and bioanalytical chemistry, 401(1), 305-313 (2011-05-17)
The roots of licorice (Glycyrrhiza glabra) are a rich source of flavonoids, in particular, prenylated flavonoids, such as the isoflavan glabridin and the isoflavene glabrene. Fractionation of an ethyl acetate extract from licorice root by centrifugal partitioning chromatography yielded 51
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