10-Gingerol
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 530429

CAS#: 23513-15-7

Description: [10]-Gingerol is a bioactive compound found in ginger (Zingiber officinale) with anti-inflammatory and antioxidant activity.


Chemical Structure

img
10-Gingerol
CAS# 23513-15-7

Theoretical Analysis

MedKoo Cat#: 530429
Name: 10-Gingerol
CAS#: 23513-15-7
Chemical Formula: C21H34O4
Exact Mass: 350.2457
Molecular Weight: 350.499
Elemental Analysis: C, 71.96; H, 9.78; O, 18.26

Price and Availability

Size Price Availability Quantity
5.0mg USD 315.0 2 Weeks
10.0mg USD 550.0 2 Weeks
1.0g USD 3650.0 2 Weeks
2.0g USD 5650.0 2 Weeks
5.0g USD 8650.0 2 Weeks
Bulk inquiry

Synonym: 10-Gingerol

IUPAC/Chemical Name: (S)- 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-tetradecanone

InChi Key: AIULWNKTYPZYAN-SFHVURJKSA-N

InChi Code: InChI=1S/C21H34O4/c1-3-4-5-6-7-8-9-10-18(22)16-19(23)13-11-17-12-14-20(24)21(15-17)25-2/h12,14-15,18,22,24H,3-11,13,16H2,1-2H3/t18-/m0/s1

SMILES Code: CCCCCCCCC[C@H](O)CC(CCC1=CC=C(O)C(OC)=C1)=O

Appearance: Oil

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:

Biological target: 10-Gingerol has anti-inflammatory, antioxidant and anti-proliferative activities.
In vitro activity: The MTT assay results demonstrated that 10-gingerol can suppress the proliferation of MDA-MB-231/IR cells in a dose and time-dependent manner (Figure 1A). The doses of 10-gingerol causing 50% growth inhibition (IC50) of MDA-MB-231/IR cells at 24 and 48 h incubations were 121.2 and 101.4 µM, respectively. In contrast, 10-gingerol demonstrated fewer anti-proliferative effects in parental MDA-MB-231 cells (Figure S1 of Supplementary Materials 1), indicating a selective anti-proliferative pattern toward radio-resistant MDA-MB-231 cells. In addition, 10-gingerol exerted fewer cytotoxic effects in MCF-10A normal mammary epithelial cells than the positive control docetaxel at two post-incubation periods [IC50 10-gingerol: 327.8 µM (24 h), and 219.8 µM (48 h); docetaxel: 3.03 µM (24 h) and 1.78 µM (48 h)] (Figure 1A).
In vivo activity: To investigate the in vivo efficacy of 10-gingerol, this study conducted a zebrafish study that induced the osteoporosis-like phenotypes by prednisolone. As shown in Figure 3A, the regenerated control scales exhibited mild TRAP activity (red color as osteoclast population) with a normal round shape, whereas the PN-treated scales had an irregular shape, resorbed edges, resorption pits, and considerably increased levels of osteoclasts present, as previously reported. 10-gingerol or GHE treatment resulted in a normal shape, few resorption sites, and decreased osteoclasts compared to PN-treated scales, as well as AL treatment. Quantitative analysis for the TRAP signal revealed significant (p < 0.01) decreases in the TRAP-positive osteoclasts in the scales treated with 10-gingerol (0.22-fold), GHE (0.34-fold), and AL (0.36-fold) compared to the PN-treated group (Figure 3B). Reference: Front Cell Dev Biol. 2021; 9: 588093. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7978033/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 65.0 185.45
DMF 30.0 85.59
Ethanol 30.0 85.59
PBS (pH 7.2) 1.0 2.85

Preparing Stock Solutions

The following data is based on the product molecular weight 350.499 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Ediriweera MK, Moon JY, Nguyen YT, Cho SK. 10-Gingerol Targets Lipid Rafts Associated PI3K/Akt Signaling in Radio-Resistant Triple Negative Breast Cancer Cells. Molecules. 2020 Jul 10;25(14):3164. doi: 10.3390/molecules25143164. PMID: 32664351; PMCID: PMC7397170. 2. Rasmussen A, Murphy K, Hoskin DW. 10-Gingerol Inhibits Ovarian Cancer Cell Growth by Inducing G2 Arrest. Adv Pharm Bull. 2019 Oct;9(4):685-689. doi: 10.15171/apb.2019.080. Epub 2019 Oct 24. PMID: 31857975; PMCID: PMC6912173. 3. Zang L, Kagotani K, Nakayama H, Bhagat J, Fujimoto Y, Hayashi A, Sono R, Katsuzaki H, Nishimura N, Shimada Y. 10-Gingerol Suppresses Osteoclastogenesis in RAW264.7 Cells and Zebrafish Osteoporotic Scales. Front Cell Dev Biol. 2021 Mar 3;9:588093. doi: 10.3389/fcell.2021.588093. PMID: 33748100; PMCID: PMC7978033. 4. Fuzer AM, Martin ACBM, Becceneri AB, da Silva JA, Vieira PC, Cominetti MR. [10]-Gingerol Affects Multiple Metastatic Processes and Induces Apoptosis in MDAMB- 231 Breast Tumor Cells. Anticancer Agents Med Chem. 2019;19(5):645-654. doi: 10.2174/1871520618666181029125607. PMID: 30370858.
In vitro protocol: 1. Ediriweera MK, Moon JY, Nguyen YT, Cho SK. 10-Gingerol Targets Lipid Rafts Associated PI3K/Akt Signaling in Radio-Resistant Triple Negative Breast Cancer Cells. Molecules. 2020 Jul 10;25(14):3164. doi: 10.3390/molecules25143164. PMID: 32664351; PMCID: PMC7397170. 2. Rasmussen A, Murphy K, Hoskin DW. 10-Gingerol Inhibits Ovarian Cancer Cell Growth by Inducing G2 Arrest. Adv Pharm Bull. 2019 Oct;9(4):685-689. doi: 10.15171/apb.2019.080. Epub 2019 Oct 24. PMID: 31857975; PMCID: PMC6912173.
In vivo protocol: 1. Zang L, Kagotani K, Nakayama H, Bhagat J, Fujimoto Y, Hayashi A, Sono R, Katsuzaki H, Nishimura N, Shimada Y. 10-Gingerol Suppresses Osteoclastogenesis in RAW264.7 Cells and Zebrafish Osteoporotic Scales. Front Cell Dev Biol. 2021 Mar 3;9:588093. doi: 10.3389/fcell.2021.588093. PMID: 33748100; PMCID: PMC7978033. 2. Fuzer AM, Martin ACBM, Becceneri AB, da Silva JA, Vieira PC, Cominetti MR. [10]-Gingerol Affects Multiple Metastatic Processes and Induces Apoptosis in MDAMB- 231 Breast Tumor Cells. Anticancer Agents Med Chem. 2019;19(5):645-654. doi: 10.2174/1871520618666181029125607. PMID: 30370858.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Joo JH, Hong SS, Cho YR, Seo DW. 10-Gingerol inhibits proliferation and invasion of MDA-MB-231 breast cancer cells through suppression of Akt and p38MAPK activity. Oncol Rep. 2016 Feb;35(2):779-84. doi: 10.3892/or.2015.4405. PubMed PMID: 26554741.

2: Bernard M, Furlong SJ, Power Coombs MR, Hoskin DW. Differential Inhibition of T Lymphocyte Proliferation and Cytokine Synthesis by [6]-Gingerol, [8]-Gingerol, and [10]-Gingerol. Phytother Res. 2015 Nov;29(11):1707-13. doi: 10.1002/ptr.5414. PubMed PMID: 26178781.

3: Ryu MJ, Chung HS. [10]-Gingerol induces mitochondrial apoptosis through activation of MAPK pathway in HCT116 human colon cancer cells. In Vitro Cell Dev Biol Anim. 2015 Jan;51(1):92-101. doi: 10.1007/s11626-014-9806-6. PubMed PMID: 25148824.

4: Ho SC, Chang KS, Lin CC. Anti-neuroinflammatory capacity of fresh ginger is attributed mainly to 10-gingerol. Food Chem. 2013 Dec 1;141(3):3183-91. doi: 10.1016/j.foodchem.2013.06.010. PubMed PMID: 23871076.

5: Chen H, Soroka DN, Haider J, Ferri-Lagneau KF, Leung T, Sang S. [10]-Gingerdiols as the major metabolites of [10]-gingerol in zebrafish embryos and in humans and their hematopoietic effects in zebrafish embryos. J Agric Food Chem. 2013 Jun 5;61(22):5353-60. doi: 10.1021/jf401501s. PubMed PMID: 23701129; PubMed Central PMCID: PMC3840088.

6: Sadakane C, Muto S, Nakagawa K, Ohnishi S, Saegusa Y, Nahata M, Hattori T, Asaka M, Takeda H. 10-Gingerol, a component of rikkunshito, improves cisplatin-induced anorexia by inhibiting acylated ghrelin degradation. Biochem Biophys Res Commun. 2011 Sep 2;412(3):506-11. doi: 10.1016/j.bbrc.2011.08.002. PubMed PMID: 21846463.

7: Dugasani S, Pichika MR, Nadarajah VD, Balijepalli MK, Tandra S, Korlakunta JN. Comparative antioxidant and anti-inflammatory effects of [6]-gingerol, [8]-gingerol, [10]-gingerol and [6]-shogaol. J Ethnopharmacol. 2010 Feb 3;127(2):515-20. doi: 10.1016/j.jep.2009.10.004. PubMed PMID: 19833188.

8: Chen CY, Li YW, Kuo SY. Effect of [10]-gingerol on [ca2+]i and cell death in human colorectal cancer cells. Molecules. 2009 Mar 2;14(3):959-69. doi: 10.3390/molecules14030959. PubMed PMID: 19255554.

9: Wang W, Li CY, Wen XD, Li P, Qi LW. Simultaneous determination of 6-gingerol, 8-gingerol, 10-gingerol and 6-shogaol in rat plasma by liquid chromatography-mass spectrometry: Application to pharmacokinetics. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Mar 15;877(8-9):671-9. doi: 10.1016/j.jchromb.2009.01.021. PubMed PMID: 19201263.

10: Park M, Bae J, Lee DS. Antibacterial activity of [10]-gingerol and [12]-gingerol isolated from ginger rhizome against periodontal bacteria. Phytother Res. 2008 Nov;22(11):1446-9. doi: 10.1002/ptr.2473. PubMed PMID: 18814211.

11: Zick SM, Djuric Z, Ruffin MT, Litzinger AJ, Normolle DP, Alrawi S, Feng MR, Brenner DE. Pharmacokinetics of 6-gingerol, 8-gingerol, 10-gingerol, and 6-shogaol and conjugate metabolites in healthy human subjects. Cancer Epidemiol Biomarkers Prev. 2008 Aug;17(8):1930-6. doi: 10.1158/1055-9965.EPI-07-2934. PubMed PMID: 18708382; PubMed Central PMCID: PMC2676573.

12: Lee S, Khoo C, Halstead CW, Huynh T, Bensoussan A. Liquid chromatographic determination of 6-, 8-, 10-gingerol, and 6-shogaol in ginger (Zingiber officinale) as the raw herb and dried aqueous extract. J AOAC Int. 2007 Sep-Oct;90(5):1219-26. PubMed PMID: 17955965.

13: Schwertner HA, Rios DC. High-performance liquid chromatographic analysis of 6-gingerol, 8-gingerol, 10-gingerol, and 6-shogaol in ginger-containing dietary supplements, spices, teas, and beverages. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Sep 1;856(1-2):41-7. PubMed PMID: 17561453.

14: Nagoshi C, Shiota S, Kuroda T, Hatano T, Yoshida T, Kariyama R, Tsuchiya T. Synergistic effect of [10]-gingerol and aminoglycosides against vancomycin-resistant enterococci (VRE). Biol Pharm Bull. 2006 Mar;29(3):443-7. PubMed PMID: 16508142.