Basic information
- CAS
77-60-1- Standard SMILES
C[C@@H]1CC[C@@]2(OC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C- InChIKey
GMBQZIIUCVWOCD-MFRNJXNGSA-N- Molecular formula
- C27H44O3
- Average molar mass
- 416.6 g/mol
- Monoisotopic mass
- 416.32904526
Overview
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.
Names & identifiers
- Preferred name
- Tigogenin
- IUPAC
- (1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-ol
- English name
- Tigogenin
- Molecular formula
- C27H44O3
- Molecular weight
- 416.64
Names & synonyms
Tigogenin77-60-15-alpha-Spirostan-3-beta-ol4SMU15RR44Spirostan-3-ol, (3beta,5alpha,25R)-CHEBI:9595DTXSID40903920NSC-93754(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-ol(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icosane-6,2'-oxane)-16-olRefChem:1100117DTXCID801331880
Show more names
Nsc93754SisalageninTIGOGENIN90%Tigogenin-RMSisal saponinSMILAGENIN(RG)Trigonegenin BTsosarsasaprgein
201-041-9(25R)-5alpha-Spirostan-3beta-olTICOGENIN(5alpha,25R)-Spirostan-3beta-olMFCD00067287(2aS,2'R,4S,5'R,6aS,6bS,8aS,8bR,9S,11aS,12aS,12bR)-5',6a,8a,9-Tetramethyldocosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-olSCHEMBL330309A1CGZ
Properties
Computed structural properties
- XLogP
- 6.5
- Topological polar surface area
- 38.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 694
Experimental & physicochemical properties
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Spirostanols and derivatives [ST0108]
SpringerMaterials PropertiesCrystal structure
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section199.26 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 202 · 202-204°C
- alpha
- -68 · -68 º (c=0.8g/100ml, CHCl3)
- Boiling point
- 474.91 °C · 474.91°C (rough estimate)
- Density
- 1.0362 · 1.0362 (rough estimate)
- refractive index
- 1.47 · 1.4700 (estimate)
- storage temp.
- -20 °C · -20°C Freezer, Under inert atmosphere
- solubility
- Chloroform (Slightly)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- rtecs
- WH1443500
Chemistry & industry
Applications
DescriptionTigogenin 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.
UsesTigogenin is a saponin structurally similar to Diosgenin (D484700) and acts as a natural plant steroid which induces apoptosis in rheumatoid arthritic fibroblast-like synoviocytes.
Upstream & downstream products
Downstream products
Related reactions
11 records
Compound notes
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