>>Signaling Pathways>> Ox Stress Reagents>> Antioxidants>>5-(3',4'-Dihydroxyphenyl)-γ-Valerolactone

5-(3',4'-Dihydroxyphenyl)-γ-Valerolactone (Synonyms: (±)-δ-(3,4-Dihydroxyphenyl)-γ-Valerolactone, 5-(3',4'-Dihydroxyphenyl)-γ-VL)

Catalog No.GC52227

An active metabolite of various polyphenols

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5-(3',4'-Dihydroxyphenyl)-γ-Valerolactone Chemical Structure

Cas No.: 21618-92-8

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5 mg
US$91.00
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10 mg
US$174.00
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25 mg
US$386.00
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50 mg
US$683.00
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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Background

5-(3',4'-Dihydroxyphenyl)-γ-valerolactone is an active metabolite of various polyphenols, including (-)-epicatechin and procyanidin .1,2 It is formed from these polyphenols by gut microbiota. 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone is an inhibitor of matrix metalloproteinase-1 (MMP-1) and MMP-2 collagen degradation activity (IC50s = 108 and 106 nM, respectively), MMP-1 and MMP-9 gelatin degradation activity (IC50s = 45.2 and 17.7 nM, respectively), and MMP-2 and MMP-9 elastin degradation activity (IC50s = 61.8 and 89 nM, respectively).3 It also scavenges free radicals in a Trolox equivalent antioxidant capacity (TEAC) assay.1

1.Unno, T., Tamemoto, K., Yayabe, F., et al.Urinary excretion of 5-(3',4'-dihydroxyphenyl)-γ-valerolactone, a ring-fission metabolite of (?)-epicatechin, in rats and its in vitro antioxidant activityJ. Agric. Food Chem.51(23)6893-6898(2003) 2.Appeldoorn, M.M., Vincken, J.-P., Aura, A.-M., et al.Procyanidin dimers are metabolized by human microbiota with 2-(3,4-dihydroxyphenyl)acetic acid and 5-(3,4-dihydroxyphenyl)-γ-valerolactone as the major metabolitesJ. Agric. Food Chem.57(3)1084-1092(2009) 3.Grimm, T., SchÄfer, A., and HÖgger, P.Antioxidant activity and inhibition of matrix metalloproteinases by metabolites of maritime pine bark extract (pycnogenol)Free Radic. Biol. Med.36(6)811-822(2004)

Chemical Properties

Cas No. 21618-92-8 SDF Download SDF
Synonyms (±)-δ-(3,4-Dihydroxyphenyl)-γ-Valerolactone, 5-(3',4'-Dihydroxyphenyl)-γ-VL
Canonical SMILES OC(C(O)=C1)=CC=C1CC2CCC(O2)=O
Formula C11H12O4 M.Wt 208.2
Solubility DMF: 10 mg/ml,DMSO: 10 mg/ml,Ethanol: Slightly soluble,PBS (pH 7.2): 0.25 mg/ml Storage -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 4.8031 mL 24.0154 mL 48.0307 mL
5 mM 0.9606 mL 4.8031 mL 9.6061 mL
10 mM 0.4803 mL 2.4015 mL 4.8031 mL
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