21618-92-8
Chemical Structure
5-(3',4'-Dihydroxyphenyl)-γ-valerolactone
- CAS No.: 21618-92-8
- Formula:C11H12O4
- Molecular Weight:208.21
IUPAC Name: 1,3-dihydroxyacridin-9(10H)-one
InChIKey: ZNXXWTPQHVLMQT-UHFFFAOYSA-N
SMILES: C1CC(=O)OC1CC2=CC(=C(C=C2)O)O
Biological Activity: 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone is an intestinal microbiota metabolite of (-)-Epicatechin (HY-N0001). 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone downregulates TNF-α-stimulated phosphorylation of IKK and IκBα, inhibits the transcriptional activation of NF-κB, and suppresses the expression of adhesion molecules and chemokines. 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone promotes autophagy, alleviates oxidative stress, maintains osteoblast differentiation, induces G1 phase arrest, inhibits adipogenesis, and scavenges ABTS free radicals. 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone inhibits the adhesion of uropathogenic Escherichia coli to bladder epithelial cells; when used in combination with Curcumin (HY-N0005), it downregulates the NLRP3 and NOX2/Nrf2 signaling pathways, thereby reducing microglial activation. 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone can be used in research related to diabetes, atherosclerosis, osteoporosis, obesity, neurodegenerative diseases involving microglial activation, and urinary tract infections[1][2][3][4][6][7][8][9].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
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5-(3',4'-Dihydroxyphenyl)-γ-valerolactone | 99.16% | 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone is an intestinal microbiota metabolite of (-)-Epicatechin (HY-N0001). 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone downregulates TNF-α-stimulated phosphorylation of IKK and IκBα, inhibits the transcriptional activation of NF-κB, and suppresses the expression of adhesion molecules and chemokines. 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone promotes autophagy, alleviates oxidative stress, maintains osteoblast differentiation, induces G1 phase arrest, inhibits adipogenesis, and scavenges ABTS free radicals. 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone inhibits the adhesion of uropathogenic Escherichia coli to bladder epithelial cells; when used in combination with Curcumin (HY-N0005), it downregulates the NLRP3 and NOX2/Nrf2 signaling pathways, thereby reducing microglial activation. 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone can be used in research related to diabetes, atherosclerosis, osteoporosis, obesity, neurodegenerative diseases involving microglial activation, and urinary tract infections. | ||||||||||||||||||||
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References
- [1]. Della Vedova L, et al. Pre-ADMET studies of 5-(3',4'-dihydroxyphenyl)-γ-valerolactone, the bioactive intestinal metabolite of proanthocyanidins. Archiv der Pharmazie. 2025 Jan;358(1):e2400575. [Content Brief]
- [2]. Lee CC, et al. 5-(3',4'-Dihydroxyphenyl-γ-valerolactone), a Major Microbial Metabolite of Proanthocyanidin, Attenuates THP-1 Monocyte-Endothelial Adhesion. International journal of molecular sciences. 2017 Jun 26;18(7):1363. [Content Brief]
- [3]. Chen F, et al. 5-(3',4'-dihydroxyphenyl)-γ-valerolactone, a microbiota metabolite of flavan-3-ols, activates SIRT1-mediated autophagy to attenuate H₂O₂-induced inhibition of osteoblast differentiation in MC3T3-E1 cells. Free radical biology & medicine. 2023 Nov 01;208:309-318. [Content Brief]
- [4]. Lee Y, et al. 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone, a metabolite of procyanidins in cacao, suppresses MDI-induced adipogenesis by regulating cell cycle progression through direct inhibition of CDK2/cyclin O. Food Funct. 2019 May 22;10(5):2958-2969. [Content Brief]
- [6]. Marcolin E, et al. A Combination of 5-(3',4'-Dihydroxyphenyl)-γ-Valerolactone and Curcumin Synergistically Reduces Neuroinflammation in Cortical Microglia by Targeting the NLRP3 Inflammasome and the NOX2/Nrf2 Signaling Pathway. Nutrients. 2025 Apr 10;17(8):1316. [Content Brief]
- [7]. Sanchez-Patan F, et al. Synthesis, analytical features, and biological relevance of 5-(3',4'-dihydroxyphenyl)-γ-valerolactone, a microbial metabolite derived from the catabolism of dietary flavan-3-ols. Journal of agricultural and food chemistry. 2011 Jul 13;59(13):7083-91. [Content Brief]
- [8]. Mena P, et al. 5‑(3′,4′‑Dihydroxyphenyl)-γ-valerolactone and its sulphate conjugates, representative circulating metabolites of flavan‑3‑ols, exhibit anti‑adhesive activity against uropathogenic Escherichia coli in bladder epithelial cells. Journal of Functional Foods. 2017 Feb;29:275‑280.
- [9]. Momma TY, et al. 5-(3',4'-Dihydroxyphenyl)-γ-Valerolactone Is a Substrate for Human Paraoxonase: A Novel Pathway in Flavan-3-ol Metabolism. Molecular nutrition & food research. 2023 Sep;67(17):e2300281. [Content Brief]
