Introduction：Basic information about CAS 42895-58-9|14-Deoxy-11,12-didehydroandrographolide, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | 14-Deoxy-11,12-didehydroandrographolide |
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| CAS Number | 42895-58-9 | Molecular Weight | 332.434 |
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| Density | 1.2±0.1 g/cm3 | Boiling Point | 519.6±50.0 °C at 760 mmHg |
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| Molecular Formula | C20H28O4 | Melting Point | 204-205ºC |
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| MSDS | ChineseUSA | Flash Point | 182.4±23.6 °C |
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Names
| Name | 14-Deoxy-11,12-didehydroandrographolide |
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| Synonym | More Synonyms |
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14-Deoxy-11,12-didehydroandrographolide BiologicalActivity
| Description | 14-Deoxy-11,12-didehydroandrographolide is an analogue of Andrographolide that can be isolated from A. paniculata. 14-Deoxy-11,12-didehydroandrographolide inhibits NF-κB activation. |
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| Related Catalog | Research Areas >>Inflammation/ImmunologyNatural Products >>Terpenoids and Glycosides |
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| Target | NF-κB |
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| In Vitro | 14-deoxy-11,12-didehydroandrographolide, a naturally occurring noncytotoxic analogue of Andrographolide, effectively reduces Ovalbumin (OVA)-induced inflammatory cell recruitment into bronchoalveolar lavage (BAL) fluid, IL-4, IL-5, IL-13, and eotaxin production, serum IgE synthesis, pulmonary eosinophilia, mucus hypersecretion, mast cell degranulation, and airway hyper-responsiveness (AHR) in a mouse asthma model, probably via inhibition of NF-κB activity[1]. |
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| In Vivo | 14-deoxy-11,12-didehydroandrographolide (1 mg/kg) dramatically reduces resistance (Rl) and restores Cdyn in OVA-challenged mice in response to methacholine[1]. |
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| Cell Assay | A549 cells (3×103/well), BEAS-2B cells (5×103/well), and RBL-2H3 cells (3×103/well) are seeded in flat-bottomed 96-well plates overnight and then incubated with increasing concentrations (3-120 μM) of 14-deoxy-11,12-didehydroandrographolide or Andrographolide for 24 and 48 h at 37°C. Cell viability is analyzed using the CellTiter 96 AQueous cell proliferation assay. This MTS assay is based on the ability of viable cells to convert a soluble tetrazolium salt to a colored formazan product. Absorbance is recorded at 490 nm[1]. |
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| Animal Admin | Mice[1] Female BALB/c mice, 6 to 8 weeks old, are sensitized and challenged with OVA. Briefly, mice are sensitized by ip injections of 20 μg of OVA and 4 mg of Al(OH)3 suspended in 0.1 mL of saline on days 0 and 14. On days 22, 23, and 24, mice are challenged with 1% OVA aerosol for 30 min. 14-deoxy-11,12-didehydroandrographolide (0.1, 0.5, and 1 mg/kg) or vehicle (1% DMSO) in 0.1 mL of saline is given by ip injections 2 h before and 10 h after each OVA aerosol challenge. Saline aerosol is used as a negative control. |
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| References | [1]. Guan SP, et al. Protective role of 14-deoxy-11,12-didehydroandrographolide, a noncytotoxic analogue ofandrographolide, in allergic airway inflammation. J Nat Prod. 2011 Jun 24;74(6):1484-90. |
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Chemical & Physical Properties
| Density | 1.2±0.1 g/cm3 |
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| Boiling Point | 519.6±50.0 °C at 760 mmHg |
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| Melting Point | 204-205ºC |
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| Molecular Formula | C20H28O4 |
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| Molecular Weight | 332.434 |
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| Flash Point | 182.4±23.6 °C |
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| Exact Mass | 332.198761 |
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| PSA | 66.76000 |
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| LogP | 1.89 |
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| Vapour Pressure | 0.0±3.1 mmHg at 25°C |
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| Index of Refraction | 1.567 |
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| InChIKey | XMJAJFVLHDIEHF-CRBRZBHVSA-N |
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| SMILES | C=C1CCC2C(C)(CO)C(O)CCC2(C)C1C=CC1=CCOC1=O |
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| Storage condition | -20°C |
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Safety Information
| RIDADR | NONH for all modes of transport |
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Synonyms
| 2(5H)-Furanone, 3-[(E)-2-[(1R,4aS,5R,6R,8aR)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethenyl]- |
| 4-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one |
| 3-{(E)-2-[(1R,4aS,5R,6R,8aR)-6-Hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl]vinyl}furan-2(5H)-one |
| 3-{(E)-2-[(1R,4aS,5R,6R,8aR)-6-Hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydro-1-naphthalenyl]vinyl}-2(5H)-furanone |
