| Identification | More | [Name]
Tigogenin | [CAS]
77-60-1 | [Synonyms]
25R,5ALPHA-SPIROSTAN-3BETA-OL
5-ALPHA, 20-ALPHA, 22-ALPHA, 25D-SPIROSTAN-3-BETA-OL
TIGOGENIN
(25r)-5-alpha-spirostan-3-beta-o
(25R)-5-Spirostan-3-ol
(3-beta,5-alpha,25r)-spirostan-3-o
5-alpha-spirostan-3-beta-ol
5alpha-Spirostan-3beta-ol, (25R)-
Spiro[8H-naphth[2',1':4,5]indeno[2,1-b]furan-8,2'-[2H]pyran], spirostan-3-ol deriv.
Spirostan-3-ol
Spirostan-3-ol, (3beta,5alpha,25R)-
Ticogenin
Tsosarsasaprgein
(5alpha,25R)-spirostan-3beta-ol
TIGOGENIN90%
SMILAGENIN(RG)
(3,5,25R)-3-Hydroxy-spirostane
(3-beta,5-alpha,25r)-spirostan-3-ol
TIGOGENIN (91%: 95%) (5A,25R)-SPIROSTAN-3B-OL)
Sisalagenin | [EINECS(EC#)]
201-041-9 | [Molecular Formula]
C27H44O3 | [MDL Number]
MFCD00067287 | [Molecular Weight]
416.64 | [MOL File]
77-60-1.mol |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
15.14±0.70(Predicted) | [color ]
Off-White | [Optical Rotation]
-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) |
| Hazard Information | Back Directory | [Description]
Tigogenin is a steroidal sapogenin that has been found in A. sisalana and has diverse biological activities.1,2,3,4 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.2 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).3 It inhibits carrageenan-induced paw edema in rats when administered at a dose of 4.2 μg/kg.4 | [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 |
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