Tetrahydrocurcumin

Base Information

• Chemical Name: Tetrahydrocurcumin
• CAS No.: 36062-04-1
• Molecular Formula: C21H24O6
• Molecular Weight: 372.418
• Hs Code.: 2914509090
• European Community (EC) Number: 609-201-3
• NSC Number: 687845
• UNII: 00U0645U03
• DSSTox Substance ID: DTXSID30865801
• Nikkaji Number: J478.221F
• Wikidata: Q27135730
• RXCUI: 1362136
• Pharos Ligand ID: PU6MSMD7RNY9
• Metabolomics Workbench ID: 38759
• ChEMBL ID: CHEMBL318743
• Mol file: 36062-04-1.mol

Synonyms:1,7-bis(4-hydroxy-3-methoxyphenyl)-3,5-heptanedione;tetrahydrocurcumin

Chemical Property of Tetrahydrocurcumin

Chemical Property:

• Melting Point: 95-97 °C
• Boiling Point: 564.1 °C at 760 mmHg
• PKA: 9.12±0.10(Predicted)
• Flash Point: 196.2 °C
• PSA: 96.22000
• Density: 1.222 g/cm³
• LogP: 3.69140
• Storage Temp.: -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 372.15728848
• Heavy Atom Count: 27
• Complexity: 437

Purity/Quality:

98% up by HPLC ^*data from raw suppliers

TetrahydroCurcumin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)CCC(=O)CC(=O)CCC2=CC(=C(C=C2)O)OC)O
• Description: Tetrahydrocurcumin (THC), the active metabolite of curcumin, is gaining popularity amongst scientist due to its wide spectrum of pharmacological activities, better stability and colourless nature. Tetrahydrocurcumin has a similar structure to that of curcumin. THC lacks the α, β-unsaturated carbonyl moiety in its chemical structure. It is naturally sourced from the roots of Curcuma zedoaria, Zingiber mioga, and Zingiber officinale and has potent antioxidant activity and depigmentation of the skin. THC is being studied for the treatment of cancer and dementia. THC is also known to epigenetically ameliorate mitochondrial dysfunction in brain vasculature during Ischemic Stroke. Tetrahydrocurcumin (THC) has been used as a neuroprotective agent to study its therapeutic potential in improving mitochondrial dysfunction in the ischemic stroke mice model.
• 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.

Technology Process of Tetrahydrocurcumin

There total 19 articles about Tetrahydrocurcumin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

C38H36O10 → 1,7-bis(4-hydroxy-3-methoxyphenyl)-heptane-3,5-dione (36062-04-1)

Guidance literature:

C₃₈H₃₆O₁₀; With sodium chloride; In water; dimethyl sulfoxide; at 150 ℃; for 3h;

With sodium; In methanol; at 20 ℃; for 3h;

Reference yield: 95.0%

1,7-bis(4’-acetoxy-3’-methoxyphenyl)-3,5-heptadione (52199-86-7) → 1,7-bis(4-hydroxy-3-methoxyphenyl)-heptane-3,5-dione (36062-04-1)

Guidance literature:

With water; sodium carbonate; sodium hydroxide; In methanol; ethanol; at 100 ℃; for 1h; Temperature; Reagent/catalyst; Solvent;

Reference yield: 92.9%

curcumin (458-37-7) → 1,7-bis(4-hydroxy-3-methoxyphenyl)-heptane-3,5-dione (36062-04-1)

Guidance literature:

With platinum-iron-nickel hydroxide composite nanoparticle catalyst; In ethanol; at 24 ℃; for 1h;

upstream raw materials:

curcumin

curcumin

vanillin

acetylacetone

Downstream raw materials:

3,5-bis<β-(4-hydroxy-3-methoxyphenyl)ethyl>pyrazole

tetrahydrocurcumin isoxazole

Refernces

• 1、 Park, Soo-Bong,Bae, Da-Woon,Clavio, Nina Abigail B.,Zhao, Lei,Jeong, Chang-Sook,Choi, Bo Mee,Macalino, Stephani Joy Y.,Cha, Hee-Jeong,Park, Jin-Byung,Lee, Jun Hyuck,Nam, Sang-Jip,Choi, Sun,Kim, Min-Kyu,Cha, Sun-Shin. "Structural and Biochemical Characterization of the Curcumin-Reducing Activity of CurA from Vibrio vulnificus". . p. 10608 - 10616. Retrieved 2018.
• 2、 -. "NOVEL TETRAHYDROCURCUMIN COMPOSITIONS, METHODS OF MAKING, AND METHODS OF USING THE SAME". . . Retrieved 2021/07/10.
• 3、 -. "Preparation method of tetrahydrocurcumin and intermediate thereof". . . Retrieved 2020/05/01.