Description
Tetrahydrocurcumin is being studied for the treatment of cancer and dementia. Tetrahydrocurcumin has been shown to have protective effects against diabetes and vascular dysfunction via alleviation of oxidative stress. Tetrahydrocurcumin is a natural functional whitening material, which is extracted from the rhizome of Curcuma longa L. It can effectively inhibit the generation of oxygen free radicals and remove the formed free radicals, and has obvious antioxidant effects, such as anti-aging of human skin, repairing, fading pigment, removing freckles, and so on. It is widely used in whitening, removing freckles, and antioxidant skin care products. It can also treat acne and reduce acne marks and pits. It has antibacterial, anti-inflammatory, antiallergenic, and analgesic effects, and can also prevent scars and fibrosis.
Synonyms
1,7-Bis(4-hydroxy-3-methoxyphenyl)-3,5-heptanedione; AS-KTC 004; HZIV 81-2; NSC 687845; Sabiwhite; Tetrahydrodiferuloylmethane
IUPAC Name
1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione
Molecular Formula
C21H24O6
Canonical SMILES
COC1=C(C=CC(=C1)CCC(=O)CC(=O)CCC2=CC(=C(C=C2)O)OC)O
InChI
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
InChIKey
LBTVHXHERHESKG-UHFFFAOYSA-N
Boiling Point
564.1±45.0 °C(Predicted)
Solubility
Soluble in DMSO (Slightly), Methanol (Slightly, Heated)
Appearance
Off-white to yellow solid
Storage
- 20 °C, Light sensitive
Chemical Properties
Off-white crystalline powder or Yellow Solid, soluble in methanol, ethanol, DMSO and other organic solvents, derived from turmeric bulbs.
Color
Light Yellow to Yellow
Definition
ChEBI: Tetrahydrocurcumin is a beta-diketone that is curcumin in which both of the double bonds have been reduced to single bonds. It has a role as a metabolite. It is a beta-diketone, a polyphenol and a diarylheptanoid. It derives from a curcumin.
Preparation
Tetrahydrocurcumin can also be chemically synthesized from curcumin by catalytic hydrogenation using PtO2 or palladium as a catalyst.One gram (1.0 g) of curcumin was dissolved in 20 ml of acetone and placed in a 100-ml glass reactor for reduction, to which was then added 500 mg of activated Raney-nickel catalyst. Subsequently, the atmosphere of the reactor was replaced for hydrogen gas by the routine method. A rubber-made balloon filled with hydrogen gas was arranged on the upper portion of the reactor in order to keep hydrogen gas pressure constant in the reactor by supplying hydrogen gas to make up for the consumed amount of hydrogen gas. The reactor was stirred while maintained at a given temperature in a constant-temperature water bath kept at 30 °C. for 2-hour reduction.After completion of the reaction, the Raney-nickel catalyst was removed from the solution by filtering, which was then evaporated and dried by concentration under reduced pressure and was dissolved again in a small amount of acetone.Subsequently, the eluate was concentrated and dried under reduced pressure to obtain 674 mg of tetrahydrocurcumin.Method for making tetrahydrocurcumin and a substance containing the antioxidative substance tetrahydrocurcumin
Stability
Light Sensitive
Uses
Tetrahydrocurcumin is an antioxidant and skin-whitening ingredient. It is a major curcuminoid metabolite of curcumin that has been shown to have protective effects against diabetes and vascular dysfunction via alleviation of oxidative stress.The interest in tetrahydrocurcumin research is increasing because it is superior to curcumin in its solubility in water, chemical stability, bioavailability, and anti-oxidative activity. Curcumin metabolizes into tetrahydrocurcumin by bacterial enzyme NADPH-dependent curcumin reductase in the intestine.
