Diosgenin

Nitogenin; (25R)-5-Spirosten-3beta-ol; 3beta-Hydroxy-5-spirostene

White to off-white powder.

512-04-9

32160000

liquid

Protect from light and moisture.

InChI=1S/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28H,6-15H2,1-4H3/t16-,17+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1

WQLVFSAGQJTQCK-VKROHFNGSA-N

Chemical. CAS: 512-04-9. Formula: C27H42O3. MW: 414.62. Diosgenin, a well-known steroid sapogenin derived from plants, has been used as a starting material for commercial synthesis of cortisone, pregnenolone, progesterone, and other steroid products. Diosgenin has shown many pharmacological activities. It exhibits anticancer, hypocholesterolemic, anti-diabetic, neuroprotective, immunomodulatory, anti-inflammatory, estrogenic, and skin protective effects. This is mainly by inducing apoptosis, suppressing malignant transformation, decreasing oxidative stress, preventing inflammatory events, promoting cellular differentiation/proliferation, and regulating T-cell immune response. It interferes with cell death pathways and their regulators to induce apoptosis. Diosgenin antagonizes tumor metastasis by modulating epithelial-mesenchymal transition and actin cytoskeleton to change cellular motility, suppressing degradation of matrix barrier, and inhibiting angiogenesis. Diosgenin has also been reported to reverse multi-drug resistance in cancer cells and sensitize cancer cells to standard chemotherapy. Additionally, diosgenin improves antioxidant status and inhibits lipid peroxidation. Its anti-inflammatory activity is through inhibiting production of pro-inflammatory cytokines, enzymes and adhesion molecules. Furthermore, diosgenin drives cellular growth/differentiation through the estrogen receptor (ER) cascade and transcriptional factor PPARgamma. Diosgenin has also be used to synthesize steroidal drugs. Several novel diosgenin analogs and nano-formulations have been synthesized with improved anti-cancer efficacy and pharmacokinetic profile.

MFCD00016887

C27H42O3

414.62

Vial

Diosgenin, a well-known steroid sapogenin derived from plants, has been used as a starting material for commercial synthesis of cortisone, pregnenolone, progesterone, and other steroid products. Diosgenin has shown many pharmacological activities. It exhibits anticancer, hypocholesterolemic, anti-diabetic, neuroprotective, immunomodulatory, anti-inflammatory, estrogenic, and skin protective effects. This is mainly by inducing apoptosis, suppressing malignant transformation, decreasing oxidative stress, preventing inflammatory events, promoting cellular differentiation/proliferation, and regulating T-cell immune response. It interferes with cell death pathways and their regulators to induce apoptosis. Diosgenin antagonizes tumor metastasis by modulating epithelial-mesenchymal transition and actin cytoskeleton to change cellular motility, suppressing degradation of matrix barrier, and inhibiting angiogenesis. Diosgenin has also been reported to reverse multi-drug resistance in cancer cells and sensitize cancer cells to standard chemotherapy. Additionally, diosgenin improves antioxidant status and inhibits lipid peroxidation. Its anti-inflammatory activity is through inhibiting production of pro-inflammatory cytokines, enzymes and adhesion molecules. Furthermore, diosgenin drives cellular growth/differentiation through the estrogen receptor (ER) cascade and transcriptional factor PPARgamma. Diosgenin has also be used to synthesize steroidal drugs. Several novel diosgenin analogs and nano-formulations have been synthesized with improved anti-cancer efficacy and pharmacokinetic profile.

>98% (HPLC)

C[C@@H](CO1)CC[C@@]21O[C@@]3([H])C[C@@]4([H])[C@]5([H])CC=C6C[C@@H](O)CC[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@@]3([H])[C@@H]2C

Soluble in ethanol (10mg/ml) or methanol. Insoluble in water or DMSO (both <1 mg/ml).

Plant

Non-hazardous

Natural Products/Extracts

12352200

Stable for at least 2 years after receipt when stored at +4°C.