Tetrahydrocurcumin
tetrahydrocurcuminoids · Tetrahydrodiferuloylmethane · SabiWhite- · 3,5-Heptanedione, 1,7-bis(4-hydroxy-3-methoxyphenyl)- · LGB-TCH · HZIV 81-2 · Nsc687845 · Aids110028
Identifikatoren & physikalische Daten
| CAS No. | 36062-04-1 |
|---|---|
| Summenformel | C21H24O6 |
| Durchschnittliche Molmasse | 372,4 g/mol |
| Monoisotopische Masse | 372,15728849 g/mol |
| SMILES | COc1cc(CCC(=O)CC(=O)CCc2ccc(O)c(OC)c2)ccc1O |
| InChIKey | LBTVHXHERHESKG-UHFFFAOYSA-N |
| PubChem CID | 124072 |
| ChEMBL | CHEMBL318743 |
| ChEBI | CHEBI:67263 |
| EC No. | 609-201-3 |
| DTXSID | DTXSID30865801 |
Chemische & physikalische Eigenschaften
| XLogP | 2,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 93,1 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 10 |
| Schwere Atome | 27 |
| Formalladung | 0 |
| Komplexität | 437 |
| Kosmetika | Antioxidant |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 95 - 97 °C95-97 ºC |
| Physical Description | Solid |
| Collision Cross Section | 181.2 Ų [M+Na]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID30865801] |
| Siedepunkt | 564.1±45.0 °C(Predicted) |
| Dichte | 1.222 |
| Flammpunkt | 196℃ |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Löslichkeit | DMSO (Slightly), Methanol (Slightly, Heated) |
| pKa (Säurekonstante) | 9.12±0.10(Predicted) |
| Aggregatzustand | powder |
| Farbe | Light Yellow to Yellow |
| BRN | 3485469 |
| Stabilität | Light Sensitive |
| Hauptanwendungen | food and beverages |
| Kosmetik-Inhaltsstoffe Funktionen | 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 (Verteilungskoeffizient) | 2.728 (est) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.Not ClassifiedAggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: 3,5-Heptanedione, 1,7-bis(4-hydroxy-3-methoxyphenyl)-Status: Active Update: 18-06-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/72833,5-Heptanedione, 1,7-bis(4-hydroxy-3-methoxyphenyl)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Hazard Classes and Categories | Not Classified |
| Wassergefährdungsklasse (WGK) | 3 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
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.
Verwenden
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.
Herstellung & Synthese
synthetische
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