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Tigogenin

Tigogenin Structure
CAS No.
77-60-1
Chemical Name:
Tigogenin
Synonyms
Nsc93754;TIGOGENIN;Ticogenin;Sisalagenin;TIGOGENIN90%;Sisal saponin;Spirostan-3-ol;SMILAGENIN(RG);Trigonegenin B;Tsosarsasaprgein
CBNumber:
CB1669512
Molecular Formula:
C27H44O3
Molecular Weight:
416.64
MOL File:
77-60-1.mol
Modify Date:
2024/8/28 13:53:21

Tigogenin 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)
form Solid
pka 15.14±0.70(Predicted)
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)

SAFETY

Risk and Safety Statements

RTECS  WH1443500

Tigogenin Chemical Properties,Uses,Production

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.

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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)- 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 (25R)-5a-Spirostan-3b-ol (25R)-3β-Hydroxy-5α-spirostane Trigonegenin B Nsc93754 22-Isoallospirostan-3β-ol (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-ol 22-Isoallospirostan-3β-ol (25R)-5.α.-Spirostan-3.β.-ol (2aS,4S,5'R,6aS,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-5',6a,8a,9-Tetramethyldocosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-ol 5α, 20α, 22α, 25D-SPIROSTAN-3β-OL Sisal saponin (2aS,4S,5'R,6aS,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-5',6a,8a,9-Tetramethyldocosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-ol 77-60-1 Miscellaneous Natural Products