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)

InChIKey

GMBQZIIUCVWOCD-YBQFXAOSNA-N

CAS DataBase Reference

77-60-1(CAS DataBase Reference)

NIST Chemistry Reference

Tigogenin(77-60-1)

Safety Information

RTECS 

WH1443500

MSDS

• Language:English Provider:(25R)-5alpha-Spirostan-3beta-ol

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.

References

[1] A.L. CRIPPS  G. B. A quantitative gas-liquid chromatographic method for the estimation of hecogenin and tigogenin in the leaves, juice and sapogenin concentrates of agave sisalana[J]. Steroids, 1978, 31 5: Pages 661-669. DOI: 10.1016/s0039-128x(78)80006-3
[2] HUA ZHOU . Tigogenin inhibits adipocytic differentiation and induces osteoblastic differentiation in mouse bone marrow stromal cells[J]. Molecular and Cellular Endocrinology, 2007, 270 1: Pages 17-22. DOI: 10.1016/j.mce.2007.01.017
[3] SUNIL KUMAR UPADHYAY . Synthesis and antifungal activity of functionalized 2,3-spirostane isomers[J]. Bioorganic & Medicinal Chemistry Letters, 2011, 21 10: Pages 2826-2831. DOI: 10.1016/j.bmcl.2011.03.092
[4] A T PEANA. Anti-inflammatory activity of aqueous extracts and steroidal sapogenins of Agave americana.[J]. Planta medica, 1997, 63 3: 199-202. DOI: 10.1055/s-2006-957652

Tigogenin(77-60-1)Related Product Information

• Ginsenoside Rh2
• Ginseng extract
• Saponin
• TRIBULOSIDE
• Hecogenin
• Diosgenin
• Escin
• PAMAQUESIDE
• DIGITONIN
• TIQUESIDE
• HECOGENIN ACETATE
• Escin sodium
• (25R)-5ALPHA-SPIROSTAN-2ALPHA,3BETA-DIOL
• Ginsenosides
• SMILAGENIN
• TIGOGENIN ACETATE
• nigrumnin I
• GSK-3 BETA