Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 00:37:26 UTC
Update Date2024-10-17 07:49:33 UTC
Metabolite IDMMDBc0031152
Metabolite Identification
Common NameTetrahydrocurcumin
DescriptionTetrahydrocurcumin (THC), is a product of the metabolism of curcumin by the enzyme NADPH-dependent curcumin reductase. Curcumin is a yellow, polyphenolic pigment, derived from the rhizomes of a plant (Curcuma longa Linn). It is the principal curcuminoid of the popular Indian spice turmeric, which is a member of the ginger family and is a natural antioxidant exhibiting a variety of pharmacological activities and therapeutic properties. It has long been used as a traditional medicine and as a preservative and coloring agent in foods. In E. coli curcumin is a substrate for the enzyme NADPH-dependent curcumin reductase which catalyzes the metal-independent reduction of curcumin to dihydrocurcumin (DHC) as an intermediate product, followed by further reduction to tetrahydrocurcumin (THC) as an end product. Tetrahydrocurcumin (THC) exhibits many of the same physiologic and pharmacological activities as curcumin and in some systems may exert greater antioxidant activity than curcumin [PMID:21467222 ]
Structure
Synonyms
ValueSource
1,7-Bis(4-hydroxy-3-methoxyphenyl)-3,5-heptanedioneChEBI
Molecular FormulaC21H24O6
Average Mass372.4117
Monoisotopic Mass372.1572885
IUPAC Name1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione
Traditional Nametetrahydrocurcumin
CAS Registry Number36062-04-1
SMILES
COC1=CC(CCC(=O)CC(=O)CCC2=CC(OC)=C(O)C=C2)=CC=C1O
InChI Identifier
InChI=1S/C21H24O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h5-6,9-12,24-25H,3-4,7-8,13H2,1-2H3
InChI KeyLBTVHXHERHESKG-UHFFFAOYSA-N