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| | 14-DEOXY-11,12-DIDEHYDROANDROGRAPHOLIDE Basic information |
| Product Name: | 14-DEOXY-11,12-DIDEHYDROANDROGRAPHOLIDE | | Synonyms: | 14-DEOXY-11,12-DIDEHYDROANDROGRAPHOLIDE;3-[(1E)-2-[(1R,4aS,5R,6R,8aR)-Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethenyl]- 2(5H)-furanone;ent-(3β,11E)-3,19-Dihydroxy-8(17),11,13-labdatrien-16,15-olide;11,12-Didehydro-14-deoxyandrographolide;14-Deoxy-11,14-didehydroandrographolide;AP 10;Deoxy-11,12-Didehydroandrographolide, 14-;3-[(E)-2-[(1R,4aβ)-2-Methylene-5α-(hydroxymethyl)-5,8aα-dimethyl-6α-hydroxydecalin-1α-yl]ethenyl]-2,5-dihydrofuran-2-one | | CAS: | 42895-58-9 | | MF: | C20H28O4 | | MW: | 332.43 | | EINECS: | 226-852-5 | | Product Categories: | | | Mol File: | 42895-58-9.mol |  |
| | 14-DEOXY-11,12-DIDEHYDROANDROGRAPHOLIDE Chemical Properties |
| Melting point | 204-205℃ | | Boiling point | 519.6±50.0 °C(Predicted) | | density | 1.17 | | storage temp. | Store at -20°C | | solubility | DMF: 10 mg/ml; DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml; DMSO: 2 mg/ml | | form | Solid | | pka | 14.80±0.70(Predicted) | | color | White to off-white | | Major Application | food and beverages | | InChI | 1S/C20H28O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h5-6,9,15-17,21-22H,1,4,7-8,10-12H2,2-3H3/b6-5+/t15-,16+,17-,19+,20+/m1/s1 | | InChIKey | XMJAJFVLHDIEHF-CRBRZBHVSA-N | | SMILES | C[C@@]1(CO)[C@H](O)CC[C@]2(C)[C@@H]1CCC(=C)[C@H]2\C=C\C3=CCOC3=O |
| WGK Germany | 3 | | Storage Class | 11 - Combustible Solids |
| | 14-DEOXY-11,12-DIDEHYDROANDROGRAPHOLIDE Usage And Synthesis |
| Description | 14-deoxy-11,12-didehydro Andrographolide is an analog of the natural diterpenoid andrographolide that can be isolated from A. paniculata. It retains the anti-inflammatory, antiallergenic, immuno-stimulatory, antiviral, antioxidant, hepatoprotective, and cardiovascular activities of andrographolide without producing cytotoxicity in KB cells (ED50 >20 μg/ml) that can occur with andrographolide 6.5 μg/ml. | | Uses | 14-Deoxy-11,12-didehydroandrographolide is the derivative of Andrographolide(A637475) is a labdane diterpenoid (2). Andrographolide is the main bioactive component isolated from the medicinal plant Andrographis paniculata (2). Andrographolide showed significant antihepatotoxic action in P. berghei K173-induced hepatic damage in M. natalensis(1). Andrographolide inhibits tumor necrosis factor-α (TNF-α)-induced intercellular adhesion mol.-1 (ICAM-1) expression and adhesion of HL-60 cells onto human umbilical vein endothelial cells (HUVEC), which are associated with inflammatory diseases (2). These findings suggest that Andrographolide may have potential as a cardiovascular-protective agent. | | Definition | ChEBI: 14-Deoxy-11,12-didehydroandrographolide is a diterpene lactone. It has a role as a metabolite. | | 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]. | | IC 50 | NF-κB | | References | [1] WENKUI LI. Secondary metabolites from Andrographis paniculata.[J]. Chemical & pharmaceutical bulletin, 2007, 55 3: 455-458. DOI: 10.1248/cpb.55.455
[2] K. JARUKAMJORN N N. Pharmacological Aspects of Andrographis paniculata on Health and Its Major Diterpenoid Constituent Andrographolide[J]. Journal of Health Science, 2008, 38 1: 370-381. DOI: 10.1248/jhs.54.370 |
| | 14-DEOXY-11,12-DIDEHYDROANDROGRAPHOLIDE Preparation Products And Raw materials |
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