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Tigogenin

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Tigogenin Basic information

Product Name:
Tigogenin
Synonyms:
  • TIGOGENIN
  • (25r)-5-alpha-spirostan-3-beta-o
  • 25R,5ALPHA-SPIROSTAN-3BETA-OL
  • 5-ALPHA, 20-ALPHA, 22-ALPHA, 25D-SPIROSTAN-3-BETA-OL
  • (25R)-5-Spirostan-3-ol
  • (3-beta,5-alpha,25r)-spirostan-3-o
  • 5-alpha-spirostan-3-beta-ol
  • 5alpha-Spirostan-3beta-ol, (25R)-
CAS:
77-60-1
MF:
C27H44O3
MW:
416.64
EINECS:
201-041-9
Product Categories:
  • Miscellaneous Natural Products
Mol File:
77-60-1.mol
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Tigogenin Chemical Properties

Melting point:
202-204°C
alpha 
-68 º (c=0.8g/100ml, CHCl3)
Boiling point:
474.91°C (rough estimate)
Density 
1.0362 (rough estimate)
refractive index 
1.4700 (estimate)
storage temp. 
-20°C Freezer, Under inert atmosphere
solubility 
Chloroform (Slightly)
pka
15.14±0.70(Predicted)
form 
Solid
color 
Off-White
optical activity
-67.218 (c 1, CHCl3)
CAS DataBase Reference
77-60-1(CAS DataBase Reference)
NIST Chemistry Reference
Tigogenin(77-60-1)
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Safety Information

RTECS 
WH1443500

MSDS

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Tigogenin Usage And Synthesis

Description

Tigogenin is a steroidal sapogenin that has been found in A. sisalana and has diverse biological activities. It increases the proliferation rate of, as well as mRNA levels of genes encoding the osteoblastic differentiation markers Cbfa1, collagen type I, and osteocalcin in, mouse bone marrow stromal cells (BMSCs) in a concentration-dependent manner. It also increases matrix calcium deposition in BMSCs when used at concentrations of 30 and 90 μM. Tigogenin is active against the fungus A. fumigatus (MIC50 = 16 μg/ml). It inhibits carrageenan-induced paw edema in rats when administered at a dose of 4.2 μg/kg.

Chemical Properties

mp 196-208C° LOD ≤0.5%

Uses

Tigogenin is a saponin structurally similar to Diosgenin (D484700) and acts as a natural plant steroid which induces apoptosis in rheumatoid arthritic fibroblast-like synoviocytes.

Definition

ChEBI: Tigogenin is a widely used steroidal sapogenin isolated from several plant species and used for synthesizing steroid drugs. It has a role as a gout suppressant and a plant metabolite.

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