5-(3',4'-Dihydroxyphenyl)-gamma-Valerolactone

5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone is an active metabolite of various polyphenols, including (-)-epicatechin (Cay-11807) and procyanidin (Cay-29763). It is formed from these polyphenols by gut microbiota. 5-(3',4'-Dihydroxyphenyl)-gamma-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). It also scavenges free radicals in a Trolox equivalent antioxidant capacity (TEAC) assay.Formal Name: 5-[(3,4-dihydroxyphenyl)methyl]dihydro-2(3H)-furanone. CAS Number: 21618-92-8. Synonyms: (±)-delta-(3,4-Dihydroxyphenyl)-gamma-Valerolactone, 5-(3',4'-Dihydroxyphenyl)-gamma-VL. Molecular Formula: C11H12O4. Formula Weight: 208.2. Purity: >95%. Formulation: (Request formulation change), A solid. Solubility: DMF: 10 mg/ml, DMSO: 10 mg/ml, Ethanol: Slightly soluble, PBS (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.