| Identification | Back Directory | [Name]
Tetrahydrocurcumin | [CAS]
36062-04-1 | [Synonyms]
LGB-TCH
Nsc687845
HZIV 81-2
Aids110028
SabiWhite-
Aids-110028
BioaActive THC
NanoActive THC
etrahydrocurcumin
TetrahydrocucuMin
Tetrahydrocurcumin
TETRAHYDROCURCUMINOID
TETRAHYDROCURCUMIN(P)
tetrahydrocurcuminoids
Tetrahydrodiferuloylmethane
36062-04-1 TETRAHYDROCURCUMIN
Tetrahydrocurcumin 36062-04-1
Tetrahydrocurcuminoids (THCs)
BioActive Tetrahydrocurcuminoids
NanoActive Tetrahydrocurcuminoids
Fat Soluble Tetrahydrocurcuminoids
Nanoactive Tetrahydrocurcumin (THC)
Cosmetic use Tetrahydrocurcuminoids
NanoLiposomal Tetrahydrocurcuminoids
Water Soluble Tetrahydrocurcuminoids
Nanoactive tetrahydrocurcuminoids THC
Tetrahydrocurcumin, 98%, from Curcuma longa L.
Tetrahydro Curcumin (Mixture of Tautomeric Isomers)
1,7-bis(4-hydroxy-3-methoxy-phenyl)heptane-3,5-dione
3,5-Heptanedione, 1,7-bis(4-hydroxy-3-methoxyphenyl)-
Soluble TETRAHYDROCURCUMINOIDS, Liposomal TETRAHYDROCURCUMINOIDS, TETRAHYDROCURCUMINOIDS NanoEmulsion, NanoActive TETRAHYDROCURCUMINOIDS | [EINECS(EC#)]
609-201-3 | [Molecular Formula]
C21H24O6 | [MDL Number]
MFCD04152347 | [MOL File]
36062-04-1.mol | [Molecular Weight]
372.41 |
| Chemical Properties | Back Directory | [Melting point ]
95-97 ºC | [Boiling point ]
564.1±45.0 °C(Predicted) | [density ]
1.222 | [Fp ]
196℃ | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly, Heated) | [form ]
powder | [pka]
9.12±0.10(Predicted) | [color ]
Light Yellow to Yellow | [BRN ]
3485469 | [Stability:]
Light Sensitive | [Major Application]
food and beverages | [Cosmetics Ingredients Functions]
ANTIOXIDANT | [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 | [SMILES]
C(C1=CC=C(O)C(OC)=C1)CC(=O)CC(=O)CCC1=CC=C(O)C(OC)=C1 | [LogP]
2.728 (est) |
| Hazard Information | Back Directory | [Description]
Tetrahydrocurcumin is a metabolite of curcumin (Item Nos. 81025 | 81025.1) that has diverse biological activities, including antioxidant, anti-inflammatory, anti-angiogenic, and anticancer properties.1,2,3,4 It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals in a cell-free assay with an EC50 value of 16.8 μM.1 Tetrahydrocurcumin (50 μM) inhibits LPS-induced increases in inducible nitric oxide synthase (iNOS) and COX-2 expression in RAW 264.7 cells.2 It also inhibits LPS-induced increases in TNF-α release when used at a concentration of 100 μM and increases in nitric oxide (NO) production and IL-6 levels in a concentration-dependent manner. Tetrahydrocurcumin reduces carrageenan-induced paw edema in rats (ED50 = 20 mg/kg).3 It also reduces the formation of neocapillaries and decreases microvascular density as well as VEGF, VEGF receptor 2 (VEGFR2), and hypoxia-inducible factor-1α (HIF-1α) expression in a CaSki cervical cancer nude mouse xenograft model when administered at doses of 100, 300, and 500 mg/kg.4 | [Chemical Properties]
Yellow Solid | [Uses]
Tetrahydro Curcumin is a major metabolite of Curcumin (C838500) that has been shown to have protective effects against diabetes and vascular dysfunction via alleviation of oxidative stress. | [Definition]
ChEBI: A beta-diketone that is curcumin in which both of the double bonds have been reduced to single bonds. | [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 | [benefits]
Tetrahydrocurcumin (ultra pure whitening element) is a natural functional whitening ingredient extracted from the roots of Ginger Curcuma longa. It has strong activity of inhibiting tyrosinase. The whitening effect is better than that of arbutin. It can effectively inhibit the generation of oxygen free radicals and remove the formed free radicals. It has obvious antioxidant, inhibits melanin, repairs freckle, anti-inflammatory activity, blocks the inflammatory process, etc. In addition, tetrahydrocurcumin has potent antioxidant activity and potential anti-aging benefits. | [Biological Activity]
Tetrahydrocurcumin is a metabolite of curcumin that has diverse biological activities, including antioxidant, anti-inflammatory, anti-angiogenic, and anticancer properties. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals in a cell-free assay with an EC50 value of 16.8 μM. Tetrahydrocurcumin (50 μM) inhibits LPS-induced increases in inducible nitric oxide synthase (iNOS) and COX-2 expression in RAW 264.7 cells. It also inhibits LPS-induced increases in TNF-α release when used at a concentration of 100 μM and increases in nitric oxide (NO) production and IL-6 levels in a concentration-dependent manner. Tetrahydrocurcumin reduces carrageenan-induced paw edema in rats (ED50 = 20 mg/kg). It also reduces the formation of neocapillaries and decreases microvascular density as well as VEGF, VEGF receptor 2 (VEGFR2), and hypoxia-inducible factor-1α (HIF-1α) expression in a CaSki cervical cancer nude mouse xenograft model when administered at doses of 100, 300, and 500 mg/kg. | [Synthesis]
The general procedure for the synthesis of tetrahydrocurcumin using (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione as starting material: 1 g of platinum-iron-nickel hydroxide composite nanoparticle catalyst was added to a reaction flask containing 300 ml of ethanol along with 100 g of curcumin, and the reaction was stirred for 1 hour at 24°C at room temperature. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give 98 g of a pale yellow viscous substance. The substance was dissolved in 400 ml of ethanol and subsequently concentrated to 150 ml. The concentrate was placed in a refrigerator and allowed to crystallize, resulting in 92.9 g of light yellow solid product in 92.9% yield. | [target]
COX | Caspase | p38MAPK | Bcl-2/Bax | p21 | VEGFR | HIF | [storage]
Store at -20°C | [References]
[1] Patent: CN104496779, 2017, B. Location in patent: Paragraph 0014; 0015; 0016; 0017; 0018-0023
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 6, p. 495 - 497
[3] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 22, p. 6175 - 6181
[4] Bioscience, biotechnology, and biochemistry, 1995, vol. 59, # 9, p. 1609 - 1612
[5] Biochemical Pharmacology, 1996, vol. 52, # 4, p. 519 - 525 |
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J & K SCIENTIFIC LTD.
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https://www.jkchemical.com |
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Energy Chemical
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400-0056266 |
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www.energy-chemical.com |
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