36062-04-1 Usage
Description
SabiWhiteis a natural, colorless, and stable derivative of curcumin, known as Tetrahydrocurcumin (THC). It is an active metabolite of curcumin, which is gaining popularity among scientists due to its wide spectrum of pharmacological activities, better stability, and colorless nature. SabiWhitepossesses potent antioxidant activity and is known for its depigmentation properties, making it a promising ingredient in the skincare industry. It is also being studied for its potential therapeutic effects in treating cancer and dementia, as well as improving mitochondrial dysfunction in the brain vasculature during ischemic stroke.
Uses
Used in Skincare Industry:
SabiWhiteis used as an antioxidant and skin-whitening ingredient for its protective effects against oxidative stress and its ability to depigment the skin.
Used in Pharmaceutical Industry:
SabiWhiteis used as a neuroprotective agent for its potential therapeutic effects in improving mitochondrial dysfunction in the ischemic stroke mice model and its potential in treating cancer and dementia.
Used in Antioxidant Applications:
SabiWhiteis used as an antioxidant for its potent antioxidant activity, which helps protect against diabetes and vascular dysfunction by alleviating oxidative stress.
Used in Solvent Applications:
SabiWhiteis used as a soluble compound in various organic solvents such as methanol, ethanol, and DMSO, making it suitable for use in a range of applications where solubility is required.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 36062-04-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,6,0,6 and 2 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 36062-04:
(7*3)+(6*6)+(5*0)+(4*6)+(3*2)+(2*0)+(1*4)=91
91 % 10 = 1
So 36062-04-1 is a valid CAS Registry Number.
InChI:InChI=1/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
36062-04-1Relevant articles and documents
Neuroprotective effects of Tetrahydrocurcumin against glutamate-induced oxidative stress in hippocampal HT22 cells
Park, Chang-Hyun,Song, Ji Hoon,Kim, Su-Nam,Lee, Ji Hwan,Lee, Hae-Jeung,Kang, Ki Sung,Lim, Hyung-Ho
, (2020)
In the central nervous system, glutamate is a major excitable neurotransmitter responsible for many cellular functions. However, excessive levels of glutamate induce neuronal cell death via oxidative stress during acute brain injuries as well as chronic neurodegenerative diseases. The present study was conducted to examine the effect of tetrahydrocurcumin (THC), a major secondary metabolite of curcumin, and its possible mechanism against glutamate-induced cell death. We prepared THC using curcumin isolated from Curcuma longa (turmeric) and demonstrated the protective effect of THC against glutamate-induced oxidative stress in HT22 cells. THC abrogated glutamate-induced HT22 cell death and showed a strong antioxidant effect. THC also significantly reduced intracellular calcium ion increased by glutamate. Additionally, THC significantly reduced the accumulation of intracellular oxidative stress induced by glutamate. Furthermore, THC significantly diminished apoptotic cell death indicated by annexin V-positive in HT22 cells. Western blot analysis indicated that the phosphorylation of mitogen-activated protein kinases including c-Jun N-terminal kinase, extracellular signal-related kinases 1/2, and p38 by glutamate was significantly diminished by treatment with THC. In conclusion, THC is a potent neuroprotectant against glutamate-induced neuronal cell death by inhibiting the accumulation of oxidative stress and phosphorylation of mitogen-activated protein kinases.
NOVEL TETRAHYDROCURCUMIN COMPOSITIONS, METHODS OF MAKING, AND METHODS OF USING THE SAME
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, (2021/07/10)
The present invention relates to novel tetrahydrocurcumin (THCu) compositions, novel methods of manufacturing, and methods of using these compositions for therapeutic applications. The novel synthetic pathway(s) result in THCu compositions that generally lack hexahydrocurcumin (HHC), and include an improved impurity profile with reduced additional species that are generally present in hydrogenated curcumin compositions.
Preparation method of tetrahydrocurcumin and intermediate thereof
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Paragraph 0068-0085, (2020/05/01)
The invention provides a preparation method of tetrahydrocurcumin and an intermediate thereof, and the preparation method of the intermediate comprises the following steps: step a, in the presence ofalkali, reacting a compound (IV) with an acetylation reagent in a solvent to obtain a compound (III); b, in the presence of a catalyst and a solvent, the compound (III) and hydrogen or a hydrogen donor are subjected to a reduction reaction to obtain a compound (II), namely the tetrahydrocurcumin intermediate; and the tetrahydrocurcumin preparation method comprises the step that acetyl is removed from the compound (II) in the solvent in the presence of alkali to obtain a compound (I), namely tetrahydrocurcumin. The selectivity of the diacetyl curcumin reduction reaction is far superior to thatof direct reduction of curcumin, and the yield is high; the method is simple and convenient in purification and high in product content, and hardly contains curcumin, hexahydrocurcumin and octahydrocurcumin; the method disclosed by the invention is simple and feasible to operate, stable and durable in process, easy to control, easy to amplify and convenient in post-reaction treatment, and can be economically and conveniently used for industrial production.
NOVEL TETRAHYDROCURCUMIN COMPOSITIONS, METHODS OF MAKING, AND METHODS OF USING THE SAME
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Paragraph 0023; 0029, (2020/09/19)
The present invention relates to novel tetrahydrocurcumin (THCu) compositions, novel methods of manufacturing, and methods of using these compositions for therapeutic applications. The novel synthetic pathway(s) result in THCu compositions that generally lack hexahydrocurcumin (HHC), and include an improved impurity profile with reduced additional species that are generally present in hydrogenated curcumin compositions.