Acetyl zingerone
Based on 1 Customer Validation
Acetyl zingerone is an analog of Zingerone (HY-14621). Acetyl zingerone downregulates the expression of ROS metabolism-related genes, fibroblast senescence-related genes, keratinocyte differentiation-related genes, and IL-17A target genes. Acetyl zingerone inhibits the activities of MMP-1, MMP-3, and MMP-12, as well as the activation of NLRP3 inflammasome, pyroptosis (pyroptosis), ferroptosis (ferroptosis), cartilage destruction, and UVA-induced cyclobutane pyrimidine dimer formation. Acetyl zingerone upregulates the expression of collagen, proteoglycan, extracellular matrix glycoprotein, Notch pathway, and GPX4 gene, activates Nrf2 and HO-1, induces extracellular matrix synthesis and PINK1/Parkin-mediated mitophagy (mitophagy), and promotes chondrocyte survival. Acetyl zingerone alleviates the progression of osteoarthritis in mice. Acetyl zingerone can be used in research related to skin aging, inflammatory skin diseases, osteoarthritis, melanoma, and non-melanoma skin cancer.
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研究用途以外に使用した場合、当社は一切の責任を負いかねます。
- 純度: 99.34%
- CAS 番号: 30881-23-3
- 分子式: C13H16O4
- 分子量:236.26
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保管条件:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
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生物活性
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化学情報
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溶剤 & 溶解度
- 純度とドキュメンテーション
- 参考文献
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Help & FAQs
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生物活性
Acetyl zingerone alters gene expression in recombinant human epidermis, upregulating genes related to the core matrix group, Notch, and ERK1/ERK2 pathways, while downregulating inflammation-related genes, as well as genes associated with the TGF-β signaling pathway and AP-1/NF-κB[1].
Acetyl zingerone (10-200 µg/mL; 6 days) dose-dependently increases the abundance of extracellular matrix proteins per cell density in cultured human skin fibroblasts[1].
Acetyl zingerone (10 µL/cm2; once daily for 4 consecutive days) doubles the dermal collagen content in ex vivo human facial skin biopsy samples[1].
Acetyl zingerone (with 1:1 serial dilutions performed starting from a stock solution prepared by dissolving 0.1 g AZ in 1 mL DMSO; 10 min (MMP-1, MMP-3); 15 min (MMP-12)) inhibits the activities of MMP-1, MMP-3 and MMP-12 in cell-free assays, with the strongest inhibitory potency against MMP-12 (IC50 = 0.255 mg), followed by MMP-3 (IC50 = 0.505 mg) and MMP-1 (IC50 = 1.065 mg)[1].
Acetyl zingerone reverses gene expression patterns associated with fibroblast senescence, keratinocyte differentiation, and IL-17A stimulation in reconstructed human epidermis[1].
Acetyl zingerone (25-200 μM; 2-48 h) exerts a protective effect on ATDC5 chondrocytes, protecting them from LPS (HY-D1056)+ ATP (HY-B2176)-induced cytotoxic damage and restoring their proliferative capacity[2].
Acetyl zingerone (100 μM; 24 h) inhibits LPS + ATP-induced pyroptosis of ATDC5 chondrocytes by alleviating cell membrane damage, suppressing NLRP3 inflammasome activation, and reducing the expression of downstream pyroptosis-related proteins[2].
Acetyl zingerone (100 μM; 24 h) attenuates LPS + ATP-induced mitochondrial damage in ATDC5 chondrocytes by reducing ROS/mtROS production and restoring mitochondrial membrane potential and structural integrity[2].
Acetyl zingerone (100 μM; 24 h pretreatment, 24 h LPS + ATP induction) activates PINK1/Parkin-mediated mitophagy in LPS + ATP-treated ATDC5 chondrocytes[2].
Acetyl zingerone (25-100 μM; 24-48 h) increases the survival rate of primary rat chondrocytes treated with IL-1β and restores their proliferative capacity[3].
Acetyl zingerone (25-100 μM; 24 h) maintains ECM homeostasis in IL-1β-treated primary rat chondrocytes and mouse ATDC5 chondrogenic cells by upregulating aggrecan and COL2A1, and downregulating matrix-degrading enzymes and inflammatory factors[3].
Acetyl zingerone (25-100 μM; 24 h) inhibits IL-1β-induced apoptosis in IL-1β-treated primary rat chondrocytes and mouse ATDC5 chondrogenic cells by upregulating Notch1 and SOCS3 and reducing the level of activated caspase-3[3].
Acetyl zingerone (25-100 μM; 24 h) reduces IL-1β-induced ROS accumulation in primary rat chondrocytes[3].
Acetyl zingerone (100 μM; 24 h) inhibits IL-1β-induced ferroptosis in primary rat chondrocytes and mouse ATDC5 chondrogenic cells by increasing GSH levels, decreasing MDA levels, stabilizing mitochondrial structure, upregulating GPX4, and activating the Nrf2/HO-1 pathway[3].
Acetyl zingerone (25 µg/mL; administered 1-6 h post-UVA irradiation) significantly reduces the formation of dark-state cyclobutane pyrimidine dimers (dark-CPD) in melanocytes of C57BL/6 mice within the first 2 hours after UVA exposure, with an inhibition rate of approximately 82% at 1 h post-irradiation, without impairing DNA repair function or cell viability[4].
Acetyl zingerone (25-50 µg/mL; 20 min pre-incubation prior to 25 min UVA irradiation) dose-dependently reduces UVA-induced ROS production in normal human neonatal epidermal keratinocytes, with reduction rates of 35% and 46%, respectively[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:Cultured human dermal fibroblasts
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Concentration:0, 10, 25, 50, 100, 200 µg/mL
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Incubation Time:6 day
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Result:Increased protein abundance per unit cell density (P < 0.05) in a dose-dependent manner for type I, IV, and VI collagens; fibromodulin; transforming growth factor-β; fibronectin; TIMP-1; and vimentin.
Showed greater abundance with higher AZ concentrations, with significant differences from control observed at specific doses (e.g., type I collagen at 100 µg/mL, type IV collagen at 50 and 100 µg/mL).
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Cell Line:ATDC5 chondrocytes
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Concentration:25, 50, 100, 200 μM
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Incubation Time:24 h, 48 h (co-treatment with LPS + ATP); 24 h (treatment with LPS + ATP), 2 h (EdU (HY-118411) incubation)
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Result:Shows no cytotoxicity at concentrations below 100 μM.
Significantly reduces cell viability at 200 μM after 24 h and 48 h.
Mitigates LPS + ATP-induced cytotoxicity, with 100 μM producing the most pronounced improvement in cell viability.
Reverses LPS + ATP-induced inhibition of chondrocyte proliferation, with 100 μM being the most effective concentration.
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Cell Line:ATDC5 chondrocytes
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Concentration:100 μM
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Incubation Time:24 h pretreatment, followed by 24 h LPS + ATP induction
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Result:Significantly increases the expression of PINK1, Parkin, and LC3-II, and decreases p62 expression in LPS + ATP-treated chondrocytes.
Enhances PINK1 and Parkin expression, which is suppressed by chloroquine (CQ) via immunofluorescence.
Increases co-localization of Parkin and LC3B with mitochondria, enhances autolysosome formation, and promotes mitophagic clearance of damaged mitochondria; these effects are attenuated by CQ.
Reduces LPS + ATP-induced ROS and mtROS production, an effect reversed by CQ.
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Cell Line:primary rat chondrocytes, mouse ATDC5 chondrogenic cells
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Concentration:25, 50 and 100 μM
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Incubation Time:24 h
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Result:Reduced IL-1β-induced apoptosis (lower early + late apoptotic cell proportion), increased cell number, upregulated Notch1 and SOCS3 expression, and decreased the cleaved caspase-3/caspase-3 ratio compared with the IL-1β-treated group.
Flow cytometry confirmed the anti-apoptotic effect at 100 μM, while crystal violet staining and western blot showed dose-dependent effects at 25, 50, and 100 μM.
Produced similar results in mouse ATDC5 cells.
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Cell Line:primary rat chondrocytes
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Concentration:100 μM
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Incubation Time:24 h
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Result:Upregulated Nrf2, HO-1, and GPX4 expression compared with the IL-1β-treated group.
Had its protective effect on GPX4 expression abolished by Nrf2 or HO-1 inhibitors, which exacerbated IL-1β-induced GPX4 suppression.
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Cell Line:C57BL/6 mouse melanocytes
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Concentration:25 µg/mL
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Incubation Time:1, 2, 4, 6 h post-UVA irradiation
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Result:Significantly reduced dark-CPD formation within the first 2 h post-irradiation, with an ~82% reduction observed after 1 h compared to controls.
Matched control CPD levels by 6 h post-irradiation, indicating no interference with DNA repair.
Left cell viability unaffected.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:C57BL/6 J (male, 8-week-old, DMM surgery-induced osteoarthritis)[2]
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Dosage:1 mg/kg
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Administration:intra-articular injection; twice a week; 8 weeks
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Result:Significantly reduced calcified menisci and bone remnants compared to the DMM-only group.
Normalized subchondral bone microarchitecture parameters, increasing bone volume/tissue volume (BV/TV) and trabecular thickness (Tb.Th) relative to the DMM-only group.
Reduced cartilage loss and proteoglycan depletion, lowering Osteoarthritis Research Society International (OARSI) scores compared to the DMM-only group.
Decreased immunohistochemical staining of pyroptosis-related protein NLRP3 and matrix-degrading protein MMP13 in cartilage tissues relative to the DMM-only group.
Increased immunohistochemical staining of mitophagy-related proteins Parkin and LC3B, as well as matrix-synthesizing protein Collagen II, in cartilage tissues relative to the DMM-only group.
化学情報
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CAS 番号 30881-23-3
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性状 Solid
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分子量 236.26
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分子式 C13H16O4
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Color White to off-white
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SMILES
O=C(C(CC1=CC=C(C(OC)=C1)O)C(C)=O)C
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輸送条件
Room temperature in continental US; may vary elsewhere.
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保管条件
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
溶剤 & 溶解度
DMSO : 100 mg/mL (423.26 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
濃度 (開始) × 体積 (開始) = 濃度 (終了) × 体積 (終了)
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 5 mg/mL (21.16 mM); Clear solution
This protocol yields a clear solution of ≥ 5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (50.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 5 mg/mL (21.16 mM); Clear solution
This protocol yields a clear solution of ≥ 5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (50.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL.
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
純度とドキュメンテーション
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データシート (291 KB)
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SDS (251 KB)
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取扱説明書 (2659 KB)
参考文献
[1]. Swindell WR, et al. A Zingerone Analog, Acetyl Zingerone, Bolsters Matrisome Synthesis, Inhibits Matrix Metallopeptidases, and Represses IL-17A Target Gene Expression. J Invest Dermatol. 2020;140(3):602-614.e15. [Content Brief]
[2]. Zhang Z, et al. Acetyl zingerone inhibits chondrocyte pyroptosis and alleviates osteoarthritis progression by promoting mitophagy through the PINK1/parkin signaling pathway. Int Immunopharmacol. 2025;161:115055. [Content Brief]
[3]. Chen X, et al. Acetyl zingerone ameliorates osteoarthritis by inhibiting chondrocyte programmed cell death. Mol Med Rep. 2023;28(5):202. [Content Brief]
[4]. Chaudhuri RK, et al. Acetyl zingerone: An efficacious multifunctional ingredient for continued protection against ongoing DNA damage in melanocytes after sun exposure ends. Int J Cosmet Sci. 2020;42(1):36-45. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 4.2326 mL | 21.1631 mL | 42.3263 mL | 105.8156 mL |
| 5 mM | 0.8465 mL | 4.2326 mL | 8.4653 mL | 21.1631 mL | |
| 10 mM | 0.4233 mL | 2.1163 mL | 4.2326 mL | 10.5816 mL | |
| 15 mM | 0.2822 mL | 1.4109 mL | 2.8218 mL | 7.0544 mL | |
| 20 mM | 0.2116 mL | 1.0582 mL | 2.1163 mL | 5.2908 mL | |
| 25 mM | 0.1693 mL | 0.8465 mL | 1.6931 mL | 4.2326 mL | |
| 30 mM | 0.1411 mL | 0.7054 mL | 1.4109 mL | 3.5272 mL | |
| 40 mM | 0.1058 mL | 0.5291 mL | 1.0582 mL | 2.6454 mL | |
| 50 mM | 0.0847 mL | 0.4233 mL | 0.8465 mL | 2.1163 mL | |
| 60 mM | 0.0705 mL | 0.3527 mL | 0.7054 mL | 1.7636 mL | |
| 80 mM | 0.0529 mL | 0.2645 mL | 0.5291 mL | 1.3227 mL | |
| 100 mM | 0.0423 mL | 0.2116 mL | 0.4233 mL | 1.0582 mL |
Acetyl zingerone 関連分類
HY-164826 関連分類
Powered by Bioz
- Acetyl zingerone
- 30881-23-3
- Interleukin Related
- Reactive Oxygen Species (ROS)
- MMP
- Pyroptosis
- Ferroptosis
- Notch
- Keap1-Nrf2
- PINK1/Parkin
- Mitophagy
- Caspase
- Apoptosis
- MMP-12
- C57BL/6 mouse melanocytes
- MMP-1
- primary rat chondrocytes
- ATDC5 chondrocytes
- NLRP3 inflammasome
- reconstructed human epidermis
- MMP-3
- normal human neonatal epidermal keratinocytes
- human dermal fibroblasts
- Inhibitor
- inhibitor
- inhibit