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14-DEOXY-11,12-DIDEHYDROANDROGRAPHOLIDE

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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
Mol File:
42895-58-9.mol
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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
pka
14.80±0.70(Predicted)
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Safety Information

WGK Germany 
3
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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.

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