p-Hydroxy-5,6-dehydrokawainCAS# 39986-86-2 |
Quality Control & MSDS
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| Cas No. | 39986-86-2 | SDF | Download SDF |
| PubChem ID | 10243535 | Appearance | Powder |
| Formula | C14H12O4 | M.Wt | 244.2 |
| Type of Compound | Phenols | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 6-[(E)-2-(4-hydroxyphenyl)ethenyl]-4-methoxypyran-2-one | ||
| SMILES | COC1=CC(=O)OC(=C1)C=CC2=CC=C(C=C2)O | ||
| Standard InChIKey | VWYHYOYHRIWSJU-QPJJXVBHSA-N | ||
| Standard InChI | InChI=1S/C14H12O4/c1-17-13-8-12(18-14(16)9-13)7-4-10-2-5-11(15)6-3-10/h2-9,15H,1H3/b7-4+ | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 4'-Hydroxy-5,6-dehydrokawain shows significant antiproliferative activity against murine colon 26-L5 carcinoma. |
| In vitro | Six new diarylheptanoids from the seeds of Alpinia blepharocalyx.[Reference: WebLink]Journal of Natural Products, 2001, 64(3):289-293.
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p-Hydroxy-5,6-dehydrokawain Dilution Calculator
p-Hydroxy-5,6-dehydrokawain Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 4.095 mL | 20.475 mL | 40.95 mL | 81.9001 mL | 102.3751 mL |
| 5 mM | 0.819 mL | 4.095 mL | 8.19 mL | 16.38 mL | 20.475 mL |
| 10 mM | 0.4095 mL | 2.0475 mL | 4.095 mL | 8.19 mL | 10.2375 mL |
| 50 mM | 0.0819 mL | 0.4095 mL | 0.819 mL | 1.638 mL | 2.0475 mL |
| 100 mM | 0.041 mL | 0.2048 mL | 0.4095 mL | 0.819 mL | 1.0238 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Synthesis of novel 5,6-dehydrokawain analogs as osteogenic inducers and their action mechanisms.[Pubmed:28427810]
Bioorg Med Chem Lett. 2017 Jun 1;27(11):2401-2406.
An imbalance between bone resorption by osteoclasts and bone formation by osteoblasts can cause bone loss and bone-related disease. In a previous search for natural products that increase osteogenic activity, we found that 5,6-dehydrokawain (1) from Alpinia zerumbet promotes osteoblastogenesis. In this study, we synthesized and evaluated series of 5,6-dehydrokawain analogs. Our structure-activity relationships revealed that alkylation of para or meta position of aromatic ring of 1 promote osteogenic activity. Among the potential analogs we synthesized, (E)-6-(4-Ethylstyryl)-4-methoxy-2H-pyran-2-one (14) and (E)-6-(4-Butylstyryl)-4-methoxy-2H-pyran-2-one (21) both significantly up-regulated Runx2 and Osterix mRNA expression at 10microM. These osteogenic activities could be mediated by bone morphogenetic protein (BMP) and activation of p38 MAPK signaling pathways. Compounds 14 and 21 also inhibited RANKL-induced osteoclast differentiation of RAW264 cells. These results indicated that novel 5,6-dehydrokawain analogs not only increase osteogenic activity but also inhibit osteoclast differentiation, and could be potential lead compounds for the development of anti-osteoporosis agents.
Syntheses and biological activities of dihydro-5,6-dehydrokawain derivatives.[Pubmed:8987662]
Biosci Biotechnol Biochem. 1996 Oct;60(10):1643-5.
The syntheses and biological activities of dihydro-5,6-dehydrokawain derivatives against plant pathogenic fungi and termites were investigated. Dihydro-5,6-dehydrokawain was isolated by a simple method without chromatography from the leaves of Alpinia speciosa K. SCHUM. The white crystalline compound obtained was identified as dihydro-5,6-dehydrokawain (1) by instrumental analyses. 4-Hydroxy-6-(2-phenylethyl)-2H-pyran-2-one (3) was prepared by hydrolyzing dihydro-5,6-dehydrokawain. Three dihydro-5,6-dehydrokawain derivatives were synthesized by reacting 3 with phosphoric agents. Among the synthesized compounds, dimethyl [6-(2-phenylethyl)-2-oxo-2H-pyran-4-yl]phosphorothionate (4) had the strongest antifungal activity of 91% at 100 ppm against Corticium rolfsii.
5,6-Dehydrokawain from Alpinia zerumbet promotes osteoblastic MC3T3-E1 cell differentiation.[Pubmed:26940726]
Biosci Biotechnol Biochem. 2016 Jul;80(7):1425-32.
Bone homeostasis is maintained by balancing bone formation and bone resorption, but an imbalance between them is associated with various bone-related diseases such as osteoporosis and rheumatoid arthritis. We found that 5,6-dehydrokawain (DK) and dihydro-5,6-dehydrokawain (DDK), which were isolated as promising compounds from Alpinia zerumbet rhizomes, promote differentiation of osteoblastic MC3T3-E1 cells. DK and DDK increased the alkaline phosphatase activity and matrix mineralization of MC3T3-E1 cells. DK exerts larger effects than DDK. The gene expression of runt-related transcription factor 2 and osterix, which are essential transcription factors in the early period of osteoblast differentiation, was significantly increased by DK treatment. The mRNA level of distal-less homeobox 5 was also enhanced by DK treatment, and DK activated the p38 mitogen-activated protein kinase pathway. Therefore, DK may have clinical potential for preventing osteoporosis, and could be considered as a potential anabolic therapeutic agent.
