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G9548

Sigma-Aldrich

Glabridin

≥98% (HPLC), powder, isoflavan

Synonym(s):

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

Empirical Formula (Hill Notation):
C20H20O4
CAS Number:
59870-68-7
Molecular Weight:
324.37
Beilstein:
7141956
MDL number:
MFCD03427694
UNSPSC Code:
12352200
PubChem Substance ID:
329799990
NACRES:
NA.77

product name

Glabridin, ≥98% (HPLC), powder

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

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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H-S Kwon et al.
Clinical and experimental immunology, 151(1), 165-173 (2007-11-17)
Inflammatory bowel disease (IBD) is characterized by detrimental immune reactivity in the gut, and the imbalance between proinflammatory and anti-inflammatory reactivity. The aims of this study were to determine whether oral administration of glabridin, a functional component of liquorice, could
Structural insights into the binding behavior of isoflavonoid glabridin with human serum albumin
Razzak MA, et al.
Food Hydrocolloids, 91, 290-300 (2019)
C V Chandrasekaran et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 18(4), 278-284 (2010-09-25)
Glycyrrhiza glabra and its phytoconstituents have been known to possess widespread pharmacological properties as an anti-inflammatory, anti-viral, antitumour and hepatoprotective drug. In this study, we examined the inhibitory potential of extract of G. glabra (GutGard™) root and its phytoconstituents (glabridin
Graziano Riccioni et al.
Nutrition (Burbank, Los Angeles County, Calif.), 28(6), 605-610 (2012-04-07)
The associations linking endothelial inflammation, endothelial oxidative stress, and atherogenesis and the potential for dietary phytonutrients to decrease the impact of these associations were assessed. A detailed literature review was conducted and summarized. A large body of scientific evidence describes
Jiyun Ahn et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 51, 439-445 (2012-09-13)
Licorice (Glycyrrhiza glabra Linne) is a well-known medicinal plant and glabridin is an isoflavan isolated from licorice. In this study, we investigated the anti-obesity effect of glabridin and glabridin-rich supercritical fluid extract of licorice (LSC). Glabridin effectively inhibited adipogenesis in
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