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3-[2-[(1R,4aβ)-2-Methylene-5α-(hydroxymethyl)-5,8aα-dimethyl-6α-hydroxydecalin-1α-yl]ethyl]-2,5-dihydrofuran-2-one

Basic information Safety Supplier Related

3-[2-[(1R,4aβ)-2-Methylene-5α-(hydroxymethyl)-5,8aα-dimethyl-6α-hydroxydecalin-1α-yl]ethyl]-2,5-dihydrofuran-2-one Basic information

Product Name:
3-[2-[(1R,4aβ)-2-Methylene-5α-(hydroxymethyl)-5,8aα-dimethyl-6α-hydroxydecalin-1α-yl]ethyl]-2,5-dihydrofuran-2-one
Synonyms:
  • 3-[2-[(1R,4aS,5R,6R,8aS)-Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethyl]-2(5H)-furanone
  • AD 04130-4
  • 3-[2-[(1R,4aβ)-2-Methylene-5α-(hydroxymethyl)-5,8aα-dimethyl-6α-hydroxydecalin-1α-yl]ethyl]-2,5-dihydrofuran-2-one
  • 3-[2-[(1R,4aβ)-Decahydro-6α-hydroxy-5α-hydroxymethyl-5,8aα-dimethyl-2-methylenenaphthalen-1α-yl]ethyl]furan-2(5H)-one
  • 3-{2-[(1R,4aS,5R,6R,8aS)-6-Hydroxy-5-(hydroxymethyl)-5,8a-dimethy l-2-methylenedecahydro-1-naphthalenyl]ethyl}-2(5H)-furanone
  • 2(5H)-Furanone,3-[2-[(1R,4aS,5R,6R,8aS)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethyl]-
  • Andrographolide Impurity 8
  • platelet activating factor,rat,bovine neutrophils,14 Deoxyandrographolide,Calcium Channel,inhibit,14-Deoxyandrographolide,Ca channels,uterine smooth muscle,Inhibitor,14Deoxyandrographolide,Ca2+ channels
CAS:
4176-97-0
MF:
C20H30O4
MW:
334.45
EINECS:
2017-001-1
Mol File:
4176-97-0.mol
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3-[2-[(1R,4aβ)-2-Methylene-5α-(hydroxymethyl)-5,8aα-dimethyl-6α-hydroxydecalin-1α-yl]ethyl]-2,5-dihydrofuran-2-one Chemical Properties

Melting point:
176-178℃
Boiling point:
509.5±50.0 °C(Predicted)
Density 
1.15
storage temp. 
Store at -20°C
solubility 
Acetonitrile: soluble
form 
A solid
pka
14.89±0.70(Predicted)
color 
White to off-white
InChI
InChI=1S/C20H30O4/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/h9,15-17,21-22H,1,4-8,10-12H2,2-3H3/t15-,16+,17-,19+,20+/m1/s1
InChIKey
GVRNTWSGBWPJGS-YSDSKTICSA-N
SMILES
O1CC=C(CC[C@H]2[C@@]3(C)[C@@]([H])([C@@](CO)(C)[C@H](O)CC3)CCC2=C)C1=O
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3-[2-[(1R,4aβ)-2-Methylene-5α-(hydroxymethyl)-5,8aα-dimethyl-6α-hydroxydecalin-1α-yl]ethyl]-2,5-dihydrofuran-2-one Usage And Synthesis

Chemical Properties

White powder, soluble in methanol, ethanol, DMSO and other organic solvents, from Andrographis paniculata (Burm. f.) Nees.

Uses

14-Deoxyandrographolide is an Ayurvedic herb Kalmegh (Andrographis paniculata) that is used to fight against respiratory viral infections.

in vivo

14-Deoxyandrographolide (40 mg/kg, intraperitoneal injection, single dose) makes rat liver cells resistant to apoptosis induced by TNF-α by downregulating the formation of death-inducing signaling complex. It enhances the activity of microsomal Ca-ATPase and increases calcium ion influx into the microsomal lumen through the NO/cGMP pathway, which in turn promotes the release of TNFRSF1A[2].

Animal Model:Male Sprague-Dawley rats[2]
Dosage:40 mg/kg; single dose
Administration:Intraperitoneal injection (i.p.)
Result:Reduced ALT elevation caused by TNF-α/ActD, reduced the number of hepatocyte apoptosis, and reduced the amount of TNF-α retained in the liver.

IC 50

Caspase 3

3-[2-[(1R,4aβ)-2-Methylene-5α-(hydroxymethyl)-5,8aα-dimethyl-6α-hydroxydecalin-1α-yl]ethyl]-2,5-dihydrofuran-2-oneSupplier

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