An active metabolite of various polyphenols
Related Products
Parent Compound(s)
11807(−)-Epicatechin 29763Procyanidin
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5-(3',4'-Dihydroxyphenyl)-γ-Valerolactone

Item No. 36690

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-[(3,4-dihydroxyphenyl)methyl]dihydro-2(3H)-furanone
CAS Number
21618-92-8
Synonyms
  • (±)-δ-(3,4-Dihydroxyphenyl)-γ-Valerolactone
  • 5-(3',4'-Dihydroxyphenyl)-γ-VL
Molecular Formula
C11H12O4
Formula Weight
208.2
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: Slightly solublePBS (pH 7.2): 0.25 mg/ml
SMILES
OC(C(O)=C1)=CC=C1CC2CCC(O2)=O
InChi Code
InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2
InChi Key
ZNXXWTPQHVLMQT-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

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    5 mg

    $74

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    10 mg

    $140

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    25 mg

    $311

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    50 mg

    $548

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    Product Description

    5-(3’,4’-Dihydroxyphenyl)-γ-valerolactone is an active metabolite of various polyphenols, including (–)-epicatechin (Item No. 11807) and procyanidin (Item No. 29763).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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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 activity. J. 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 metabolites. J. 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).