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18β-Glycyrrhetinic Acid

18β-Glycyrrhetinic Acid

Product ID G4597
Cas No. 471-53-4
Purity ≥98%
Product Unit SizeCostQuantityStock
5 g $84.10 In stock
10 g $138.30 In stock
25 g $252.30 In stock
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  • Product Info
  • Shipping and Storage
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  • References
  • Description
  • Product Info
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Description

18β-Glycyrrhetinic Acid (enoxolone) is a triterpene glycoside found in Glycyrrhiza that exhibits anti-hyperlipidemic, anti-obesity, anti-inflammatory, anticancer, and anti-metastatic activities. Enoxolone is commercially used as a flavorant. Enoxolone inhibits 15-hydroxyprostaglandin dehydrogenase, altering the metabolism of prostaglandins E2 (PGE2) and F2 (PGF2). Enoxolone also modulates ion channel activity, inhibiting human ether-related-a-go-go (hERG) K+ channels and Kv1.3 K+ channels. In vitro, enoxolone prevents production of IL-2 and activation of T cells. In other cellular models, enoxolone decreases cellular invasion, expression of matrix metalloproteinase 9 (MMP9) and VEGF, and activity of NF-κB. This compound also induces apoptosis in non-small cell lung cancer (NSCLC) cells, decreasing expression of Bcl-2, Bcl-xl, cyclin D1, and cyclin E, increasing activation of caspases and PARP, and downregulating phosphorylation of JNK and PKC. In animal models, enoxolone inhibits anandamide-induced adipocyte differentiation, suppresses expression of fatty acid synthase, and decreases plasma lipid levels, fat weight, and body weight.

Product Info

Cas No.

471-53-4

Purity

≥98%

Formula

C30H46O4

Formula Wt.

470.68

Chemical Name

(3β,20β)-3-Hydroxy-11-oxoolean-12-en-29-oic acid

IUPAC Name

(2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9, 12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12, 14b-dodecahydro-1H-picene-2-carboxylic acid

Synonym

Enoxolone, Uralenic acid, Arthrodont, Biosone

Melting Point

296°C

Solubility

Soluble in ethanol, chloroform, dioxone, pyridine or acetic acid.

Appearance

White to off white powder

Shipping and Storage

Store Temp

Ambient

Ship Temp

Ambient

Downloads

MSDS

G4597 MSDS PDF

Info Sheet

G4597 Info Sheet PDF

References

Jayasooriya RG, Dilshara MG, Park SR, et al. 18β-Glycyrrhetinic acid suppresses TNF-α induced matrix metalloproteinase-9 and vascular endothelial growth factor by suppressing the Akt-dependent NF-κB pathway. Toxicol In Vitro. 2014 Aug;28(5):751-8. PMID: 24613819.

Park M, Lee JH, Choi JK, et al. 18β-glycyrrhetinic acid attenuates anandamide-induced adiposity and high-fat diet induced obesity. Mol Nutr Food Res. 2014 Jul;58(7):1436-46. PMID: 24687644.

Song J, Ko HS, Sohn EJ, et al. Inhibition of protein kinase C α/βII and activation of c-Jun NH2-terminal kinase mediate glycyrrhetinic acid induced apoptosis in non-small cell lung cancer NCI-H460 cells. Bioorg Med Chem Lett. 2014 Feb 15;24(4):1188-91. PMID: 24461294.

Wu D, Jiang L, Wu H, et al. Inhibitory effects of glycyrrhetinic Acid on the delayed rectifier potassium current in Guinea pig ventricular myocytes and HERG channel. Evid Based Complement Alternat Med. 2013;2013:481830. PMID: 24069049.

Fu XX, Du LL, Zhao N, et al. 18β-Glycyrrhetinic acid potently inhibits Kv1.3 potassium channels and T cell activation in human Jurkat T cells. J Ethnopharmacol. 2013 Jul 9;148(2):647-54. PMID: 23707333.

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