Zingerone

Alias: Gingerone; Zingerone; AI331837; AI3 31837; AI3-31837
Cat No.:V13889 Purity: ≥98%
Zingerone (Vanillylacetone) is a non-toxic methoxyphenol obtained from ginger and has anti~inflammatory, anti-diabetic, anti-lipid allergy, anti-diarrheal, anti-spasmodic and anti-tumor activities.
Zingerone Chemical Structure CAS No.: 122-48-5
Product category: NF-κB
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
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500mg
1g
5g
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Product Description
Zingerone (Vanillylacetone) is a non-toxic methoxyphenol obtained from ginger and has anti~inflammatory, anti-diabetic, anti-lipid allergy, anti-diarrheal, anti-spasmodic and anti-tumor activities. Zingerone can alleviate oxidative stress and inflammation and downregulate NF-κB-mediated signaling pathways. Zingerone works as an antimitotic agent and suppresses the growth of neuroblastoma.
Biological Activity I Assay Protocols (From Reference)
Targets
NF-κB
ln Vitro
Zingerone is a non-toxic methoxyphenol that has powerful anti-inflammatory, anti-diabetic, anti-lipolytic, anti-diarrheic, and antispasmodic properties[1].
Zingerone (0–2 mM) reduces neoblastoma cell survival[3].
Zingerone (0–2 mM) decreases cyclin D1 expression and increases caspase-3 and PARP-1 cleavage in BE(2)-M17 cells[3].
ln Vivo
Zingerone (50, 100 mg/kg, p.o. daily for 21 days) protects against alloxan-induced diabetes in rats by reducing oxidative stress and inflammation[2].
Zingerone (10 mg/kg, i.p.) slows the growth of tumors by stopping the mitotic cycle, preventing cell division, and inducing apoptosis[3].
References

[1]. A Review on Pharmacological Properties of Zingerone (4-(4-Hydroxy-3-methoxyphenyl)-2-butanone). ScientificWorldJournal. 2015;2015:816364.

[2]. Zingerone (4-(4-hydroxy-3-methylphenyl) butan-2-one) protects against alloxan-induced diabetes via alleviation of oxidative stress and inflammation: Probable role of NF-kB activation. Saudi Pharm J. 2018 Dec;26(8):1137-1145.

[3]. Zingerone Suppresses Tumor Development through Decreasing Cyclin D1 Expression and Inducing Mitotic Arrest. Int J Mol Sci. 2018 Sep 19;19(9).

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H14O3
Molecular Weight
194.23
Exact Mass
194.0943
Elemental Analysis
C, 68.02; H, 7.27; O, 24.71
CAS #
122-48-5
Related CAS #
122-48-5
Appearance
Solid powder
SMILES
CC(=O)CCC1=CC(=C(C=C1)O)OC
InChi Key
OJYLAHXKWMRDGS-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H3
Chemical Name
4-(4-hydroxy-3-methoxyphenyl)butan-2-one
Synonyms
Gingerone; Zingerone; AI331837; AI3 31837; AI3-31837
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

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
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: 38~100 mg/mL (195.6~514.9 mM)
Water: ~10 mg/mL (~51.5 mM)
Ethanol: ~38 mg/mL (~195.6 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.87 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 (12.87 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 (12.87 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 5.1485 mL 25.7427 mL 51.4854 mL
5 mM 1.0297 mL 5.1485 mL 10.2971 mL
10 mM 0.5149 mL 2.5743 mL 5.1485 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

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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?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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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:
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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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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.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT05779280 Active
Recruiting
Other: THDA + Acetyl Zingerone
Topical Product
Other: THDA
Wrinkle
Skin Pigmentation
Integrative Skin Science and
Research
April 6, 2023 Not Applicable
NCT03530787 Completed Other: Acetyl Zingerone Topical
Cream
Other: Topical cream
Wrinkle Appearance
Skin Pigment
University of California, Davis December 11, 2017 Not Applicable
Biological Data
  • Chemical structure of zingerone. IUPAC name: [4-(3-methoxy-4-hydroxyphenyl)-butan-2-one]. ScientificWorldJournal . 2015:2015:816364.
  • Pharmacological dimensions of zingerone. ScientificWorldJournal . 2015:2015:816364.
  • Effect of Zingerone on Glycosylation of Hb levels in different experimental groups: Group-I: normal control; Group-II: diabetic control; Group-III: diabetic rats treated with zingerone (50 mg/kg bw/day); Group-IV: diabetic rats treated with zingerone (100 mg/kg bw/day); Group-V: Diabetic rats treated with glibenclamide 4.5 mg/kg bw/day). Saudi Pharm J . 2018 Dec;26(8):1137-1145.
  • Effect of Zingerone on NF-κB-p65 levels in different experimental groups: Group-I: normal control; Group-II: diabetic control; Group-III: diabetic rats treated with zingerone (50 mg/kg bw/day); Group-IV: diabetic rats treated with zingerone (100 mg/kg bw/day); Group-V: Diabetic rats treated with glibenclamide 4.5 mg/kg bw/day). Saudi Pharm J . 2018 Dec;26(8):1137-1145.
  • Effect of Zingerone on TNF-α levels in different experimental groups: Group-I: normal control; Group-II: diabetic control; Group-III: diabetic rats treated with zingerone (50 mg/kg bw/day); Group-IV: diabetic rats treated with zingerone (100 mg/kg bw/day); Group-V: Diabetic rats treated with glibenclamide 4.5 mg/kg bw/day). Saudi Pharm J . 2018 Dec;26(8):1137-1145.
  • Effects of zingerone on viability of neuroblastoma cell lines. Int J Mol Sci . 2018 Sep 19;19(9):2832.
  • Effects of zingerone on cell-cycle arrest in BE(2)-M17 cells. Int J Mol Sci . 2018 Sep 19;19(9):2832.
  • Effect of zingerone on the expressions of cell-cycle-associated proteins and apoptosis in BE(2)-M17 cells. Int J Mol Sci . 2018 Sep 19;19(9):2832.
  • Effect of zingerone on tumor growth and expressions of cell-cycle-regulatory protein in an in vivo mouse tumor model. Int J Mol Sci . 2018 Sep 19;19(9):2832.
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