OctahydrocurcuminCAS# 36062-07-4 |
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| Cas No. | 36062-07-4 | SDF | Download SDF |
| PubChem ID | 13888132 | Appearance | Powder |
| Formula | C21H28O6 | M.Wt | 376.44 |
| Type of Compound | Phenols | Storage | Desiccate at -20°C |
| Synonyms | Hexahydrobisdemethoxycurcumin | ||
| Solubility | DMSO : 100 mg/mL (265.65 mM; Need ultrasonic) | ||
| Chemical Name | (3S,5S)-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-diol | ||
| SMILES | COC1=C(C=CC(=C1)CCC(CC(CCC2=CC(=C(C=C2)O)OC)O)O)O | ||
| Standard InChIKey | OELMAFBLFOKZJD-IRXDYDNUSA-N | ||
| Standard InChI | InChI=1S/C21H28O6/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/h5-6,9-12,16-17,22-25H,3-4,7-8,13H2,1-2H3/t16-,17-/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Octahydrocurcumin has antioxidant and and anti-inflammatory activities, it can inhibit the lipopolysaccharide (LPS)-induced inflammatory response via the mechanism of inhibiting NF-κB translocation to the nucleus. Octahydrocurcumin exhibits potent cytotoxic effect (IC50 =19.46 ug/mL) and shows high antimicrobial activity. |
| Targets | NF-kB | Antifection |
| In vitro | Different Curcuminoids Inhibit T-Lymphocyte Proliferation Independently of Their Radical Scavenging Activities[Reference: WebLink]Pharmaceutical Research,2008, 25,(8):1822-7.We investigated the inhibitory effects of curcumin, curcumin derivatives and degradation products on OKT3-induced human peripheral blood mononuclear cell (PBMC) proliferation and the role of their radical scavenging activity.
Comparative antioxidant activities of curcumin and its demethoxy and hydrogenated derivatives.[Pubmed: 17202663]Biol.Pharm. Bull., 2007, 30(1):74-8.
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Octahydrocurcumin Dilution Calculator
Octahydrocurcumin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.6565 mL | 13.2823 mL | 26.5647 mL | 53.1293 mL | 66.4116 mL |
| 5 mM | 0.5313 mL | 2.6565 mL | 5.3129 mL | 10.6259 mL | 13.2823 mL |
| 10 mM | 0.2656 mL | 1.3282 mL | 2.6565 mL | 5.3129 mL | 6.6412 mL |
| 50 mM | 0.0531 mL | 0.2656 mL | 0.5313 mL | 1.0626 mL | 1.3282 mL |
| 100 mM | 0.0266 mL | 0.1328 mL | 0.2656 mL | 0.5313 mL | 0.6641 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Octahydrocurcumin is a hydrogenated derivatives of curcumin; metabolite of curcumin. IC50 value: Target: OKT3-induced PBMC proliferation was inhibited by octahydrocurcumin with IC50 of 82 uM. The investigated substances with the strongest effect on radical scavenging were tetrahydro-, hexahydro-, and octahydrocurcumin with IC50 values of 10.0, 11.7, and 12.3 microM, respectively [1]. curcumin and tetrahydrocurcumin significantly inhibited the release of prominent cytokines, including tumor necrosis factor?α (TNF?α) and interleukin?6 (IL?6); however, hexahydrocurcumin and octahydrocurcumin did not significantly alter cytokine release [2]. Hydrogenated derivatives of curcumin exhibited stronger DPPH scavenging activity compared to curcumin and a reference antioxidant, trolox. The scavenging activity significantly decreased in the order THC>HHC=OHC>trolox>curcumin>Dmc>>>Bdmc [3].
References:
[1]. Deters M, et al. Different curcuminoids inhibit T-lymphocyte proliferation independently of their radical scavenging activities. Pharm Res. 2008 Aug;25(8):1822-7.
[2]. Zhao F, et al. Curcumin and its major metabolites inhibit the inflammatory response induced by lipopolysaccharide: Translocation of nuclear factor-κB as potential target. Mol Med Rep. 2015 Apr;11(4):3087-93.
[3]. Somparn P, et al. Comparative antioxidant activities of curcumin and its demethoxy and hydrogenated derivatives. Biol Pharm Bull. 2007 Jan;30(1):74-8.
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Comparative antioxidant activities of curcumin and its demethoxy and hydrogenated derivatives.[Pubmed:17202663]
Biol Pharm Bull. 2007 Jan;30(1):74-8.
The antioxidant activities of curcumin, its natural demethoxy derivatives (demethoxycurcumin, Dmc and bisdemethoxycurcumin, Bdmc) and metabolite hydrogenated derivatives (tetrahydrocurcumin, THC; hexahydrocurcumin, HHC; Octahydrocurcumin; OHC) were comparatively studied using 2,2-diphenyl-1-picrylhydrazyl (DDPH) radical, 2,2'-azobis(2-amidinopropane)dihydrochloride (AAPH) induced linoleic oxidation and AAPH induced red blood cell hemolysis assays. Hydrogenated derivatives of curcumin exhibited stronger DPPH scavenging activity compared to curcumin and a reference antioxidant, trolox. The scavenging activity significantly decreased in the order THC>HHC=OHC>trolox>curcumin>Dmc>>>Bdmc. Stronger antioxidant activities toward lipid peroxidation and red blood cell hemolysis were also demonstrated in the hydrogenated derivatives. By the model of AAPH induced linoleic oxidation, the stoichiometric number of peroxyl radical that can be trapped per molecule (n) of hydrogenated derivatives were 3.4, 3.8 and 3.1 for THC, HHC and OHC, respectively. The number (n) of curcumin and Dmc were 2.7 and 2.0, respectively, which are comparable to trolox, while it was 1.4 for Bdmc. The inhibition of AAPH induced red blood cell hemolysis significantly decreased in the order OHC>THC=HHC>trolox>curcumin=Dmc. Results in all models demonstrated the lower antioxidant activity of the demethoxy derivatives, suggesting the ortho-methoxyphenolic groups of curcumin are involved in antioxidant activities. On the other hand, hydrogenation at conjugated double bonds of the central seven carbon chain and beta diketone of curcumin to THC, HHC and OHC remarkably enhance antioxidant activity.
