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Hexahydrocurcumin

Cat No.:V30758 Purity: ≥98%
Hexahydrocurcumin is one of the major metabolites of curcumin and a selective orally bioactive COX-2 inhibitor (antagonist) with no activity against COX-1.
Hexahydrocurcumin
Hexahydrocurcumin Chemical Structure CAS No.: 36062-05-2
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
10mg
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Product Description
Hexahydrocurcumin is one of the major metabolites of curcumin and a selective orally bioactive COX-2 inhibitor (antagonist) with no activity against COX-1. Hexahydrocurcumin has antioxidant, anticancer and anti~inflammatory effects.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Hexahydrocurcumin (0-25 μM; 24-48 hours; HT-29 cells) treatment dramatically decreased the viability of HT-29 colon cancer cells in a way that was dependent on both time and concentration. Hexahydrocurcumin's IC50 values were 56.95 and 77.05 after 24 and 48 hours of exposure, respectively [1]. Combining 5-fluorouracil (5-FU; 5 μM) with hexahydrocurcumin (0-25 μM; 24-48 hours; HT-29 cells) dramatically decreased COX-2 expression. Levels of COX-1 remain constant [1]. COX-2 protein was dramatically reduced by hexahydrocurcumin (0-25 μM; 24-48 hours; HT-29 cells) in combination with 5-fluorouracil (5-FU; 5 μM). The amounts of COX-1 protein are unaltered [1]. In murine macrophages (RAW 264.7), lipopolysaccharide (LPS)-induced rise in prostaglandin E2 (PGE2) is attenuated in a concentration-dependent manner by hexahydrocurcumin (7–14 μM; 24 hours) [2].
ln Vivo
Rats with colon cancer who received oral hexahydrocurcumin treatment (50 mg/kg; daily; for 16 weeks; male Wistar rats) had a significant decrease in the number of aberrant crypt foci (ACF). Moreover, hexahydrocurcumin dramatically lowered COX-2 protein expression. Rats with normal COX-1 protein levels are not different [3].
Cell Assay
Cell Viability Assay[1]
Cell Types: HT-29 Cell
Tested Concentrations: 0 µM, 5 µM, 10 µM, 25 µM
Incubation Duration: 24 hrs (hours) or 48 hrs (hours)
Experimental Results: Dramatically diminished the viability of HT-29 colon cancer cells.

RT-PCR[1]
Cell Types: HT-29 Cell
Tested Concentrations: 25 µM
Incubation Duration: 24 hrs (hours)
Experimental Results: Combination with 5-fluorouracil (5-FU; 5 µM) Dramatically diminished COX-2 expression.

Western Blot Analysis[1]
Cell Types: HT-29 Cell
Tested Concentrations: 25 µM
Incubation Duration: 24 hrs (hours)
Experimental Results: Combined use with 5-fluorouracil (5-FU; 5 µM) Dramatically diminished COX-2 protein.
Animal Protocol
Animal/Disease Models: Male Wistar rats (100-120 g) were injected with dimethylhydrazine (DMH) [3]
Doses: 50 mg/kg
Route of Administration: Oral; injection. Daily; continued for 16 weeks
Experimental Results: The amount of ACF was Dramatically diminished in rats with colon cancer. COX-2 protein expression was also Dramatically diminished.
References

[1]. Hexahydrocurcumin enhances inhibitory effect of 5-fluorouracil on HT-29 human colon cancer cells. World J Gastroenterol. 2012 May 21;18(19):2383-9.

[2]. In vitro antioxidant and anti-inflammatory activities of 1-dehydro-[6]-gingerdione, 6-shogaol, 6-dehydroshogaol and hexahydrocurcumin. Food Chem. 2012 Nov 15;135(2):332-7.

[3]. Effects of hexahydrocurcumin in combination with 5-fluorouracil on dimethylhydrazine-induced colon cancer in rats. World J Gastroenterol. 2012 Dec 21;18(47):6951-9.

Additional Infomation
Hexahydrocurcumin is a diarylheptanoid.
Hexahydrocurcumin has been reported in Zingiber officinale with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H32O6
Molecular Weight
380.47518
Exact Mass
374.172
CAS #
36062-05-2
PubChem CID
5318039
Appearance
White to yellow solid powder
Density
1.2±0.1 g/cm3
Boiling Point
622.6±55.0 °C at 760 mmHg
Melting Point
80-82℃
Flash Point
218.4±25.0 °C
Vapour Pressure
0.0±1.9 mmHg at 25°C
Index of Refraction
1.583
LogP
1.49
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
10
Heavy Atom Count
27
Complexity
442
Defined Atom Stereocenter Count
0
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~267.07 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.68 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (6.68 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (6.68 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.6283 mL 13.1413 mL 26.2826 mL
5 mM 0.5257 mL 2.6283 mL 5.2565 mL
10 mM 0.2628 mL 1.3141 mL 2.6283 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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