[10]-Shogaol is an antioxidant found in ginger that is used as a skin cell growth/proliferation and migration enhancer. [10]-Shogaol1 inhibits COX-2 with IC50 of 7.5 μM and has anti-proliferation activity.

Physicochemical Properties

Molecular Formula	C21H32O3
Molecular Weight	332.4770
Exact Mass	332.235
CAS #	36752-54-2
PubChem CID	6442612
Appearance	Colorless to light yellow liquid
LogP	5.599
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	13
Heavy Atom Count	24
Complexity	351
Defined Atom Stereocenter Count	0
SMILES	O=C(C([H])([H])C([H])([H])C1C([H])=C([H])C(=C(C=1[H])OC([H])([H])[H])O[H])/C(/[H])=C(\[H])/C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]
InChi Key	FADFGCOCHHNRHF-VAWYXSNFSA-N
InChi Code	InChI=1S/C21H32O3/c1-3-4-5-6-7-8-9-10-11-12-19(22)15-13-18-14-16-20(23)21(17-18)24-2/h11-12,14,16-17,23H,3-10,13,15H2,1-2H3/b12-11+
Chemical Name	(E)-1-(4-hydroxy-3-methoxyphenyl)tetradec-4-en-3-one
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: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	- Cyclooxygenase-2 (COX-2): [10]-Shogaol inhibits COX-2 activity with an IC50 of 2.7 μM; it shows no significant inhibition on COX-1 (IC50 > 100 μM), indicating high selectivity for COX-2 [2] - Drug resistance-related transporters (ABCG2, MRP1): [10]-Shogaol downregulates the expression of these transporters in docetaxel-resistant prostate cancer cells[3]
ln Vitro	- Skin cell proliferation and migration promotion [1] - On HaCaT human keratinocytes: [10]-Shogaol (1 μM, 5 μM, 10 μM) increased cell proliferation by 15%, 32%, and 45% respectively (48 h, MTT assay) vs. control. In the scratch wound healing assay, 5 μM [10]-Shogaol accelerated wound closure rate by 58% at 24 h and 72% at 48 h vs. control. - Antioxidant activity: It scavenged DPPH radicals with an EC50 of 8.3 μM and ABTS radicals with an EC50 of 6.1 μM. It also reduced H₂O₂-induced intracellular ROS levels in HaCaT cells by 42% (5 μM, 2 h treatment) [1] - COX-2 inhibitory activity [2] - In a cell-free COX-2 assay: [10]-Shogaol (0.1–10 μM) inhibited COX-2-mediated prostaglandin E2 (PGE2) production in a dose-dependent manner. At 5 μM, it reduced PGE2 levels by 89% vs. the enzyme-only control [2] - Antiproliferative and drug resistance-modulating activity in prostate cancer cells [3] - On docetaxel-resistant DU145 (DU145/DocR) cells: [10]-Shogaol inhibited proliferation with an IC50 of 12.5 μM (72 h, MTT assay). It downregulated the expression of ABCG2 (protein level reduced by 65% at 10 μM) and MRP1 (protein level reduced by 58% at 10 μM) via western blot. It also sensitized DU145/DocR cells to docetaxel, reducing the docetaxel IC50 from 80 nM to 22 nM (10 μM [10]-Shogaol pretreatment) [3]
Enzyme Assay	- Reaction system preparation: The assay mixture (200 μL total volume) contained 50 mM Tris-HCl buffer (pH 8.0), 1 μM heme, 100 μM arachidonic acid (substrate), recombinant human COX-2 enzyme, and serial dilutions of [10]-Shogaol (0.1–10 μM). The control group lacked [10]-Shogaol. - Incubation and detection: The mixture was incubated at 37°C for 15 minutes to allow PGE2 synthesis. The reaction was terminated by adding 5 μL of 1 M HCl. PGE2 concentration was measured using a competitive ELISA kit, with absorbance read at 450 nm. The IC50 was calculated by fitting the dose-response curve of PGE2 inhibition [2]
Cell Assay	- HaCaT cell proliferation and migration assays [1] - Proliferation assay (MTT): HaCaT cells were seeded in 96-well plates (5×10³ cells/well) and incubated overnight. [10]-Shogaol (0.5–20 μM) was added, and cells were incubated for 24 h/48 h. MTT reagent was added, incubated for 4 h, formazan dissolved in DMSO, and absorbance measured at 570 nm. Proliferation rate was calculated vs. control. - Wound healing assay: HaCaT cells were seeded in 6-well plates and grown to 100% confluence. A scratch was made with a pipette tip; [10]-Shogaol (1–10 μM) was added. Images were taken at 0 h, 24 h, 48 h, and wound closure rate was calculated as [(initial wound width – final wound width)/initial wound width] × 100% [1] - DU145/DocR prostate cancer cell assays [3] - Proliferation assay (MTT): DU145/DocR cells were seeded in 96-well plates (3×10³ cells/well) and treated with [10]-Shogaol (2.5–40 μM) for 72 h. MTT assay was performed as above to calculate IC50. - Drug resistance factor detection (western blot): Cells were treated with [10]-Shogaol (5 μM, 10 μM) for 48 h, lysed with RIPA buffer. Equal amounts of protein were separated by SDS-PAGE, transferred to PVDF membranes, and probed with anti-ABCG2 and anti-MRP1 antibodies. Band intensity was quantified vs. GAPDH (loading control) [3]
References	[1]. 10-Shogaol, an antioxidant from Zingiber officinale for skin cell proliferation and migration enhancer. Int J Mol Sci. 2012;13(2):1762-77. [2]. Cyclooxygenase-2 inhibitors in ginger (Zingiber officinale). Fitoterapia. 2011 Jan;82(1):38-43. [3]. Ginger Phytochemicals Inhibit Cell Growth and Modulate Drug Resistance Factors in Docetaxel Resistant Prostate Cancer Cell. Molecules. 2017 Sep 5;22(9). pii: E1477.
Additional Infomation	[10]-Shogaol is a monomethoxybenzene, a member of phenols and an enone. [10]-Shogaol has been reported in Zingiber officinale with data available. See also: Ginger (part of). - [10]-Shogaol is a bioactive phenol derived from the rhizome of Zingiber officinale (ginger), formed by dehydration of [6]-gingerol during ginger processing (e.g., drying, heating) [1,2,3] - Mechanisms of action: [1] Antioxidant activity via scavenging free radicals (DPPH/ABTS) and reducing intracellular ROS; promotes HaCaT cell migration possibly by activating the ERK1/2 signaling pathway (phospho-ERK1/2 upregulated by 2.3-fold at 5 μM). [2] Selective COX-2 inhibition by binding to the enzyme’s active site, blocking arachidonic acid conversion to PGE2. [3] Sensitizes docetaxel-resistant prostate cancer cells by downregulating ABCG2/MRP1 (ATP-binding cassette transporters that efflux chemotherapeutics) [1,2,3]

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~300.77 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (7.52 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 (7.52 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (7.52 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	3.0077 mL	15.0385 mL	30.0770 mL
	5 mM	0.6015 mL	3.0077 mL	6.0154 mL
	10 mM	0.3008 mL	1.5038 mL	3.0077 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.