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| | Diosgenin Basic information |
| | Diosgenin Chemical Properties |
| Melting point | 205-208°C | | Boiling point | 473.46°C (rough estimate) | | alpha | D25 -129° (c = 1.4 in CHCl3) | | density | 1.0483 (rough estimate) | | refractive index | 1.4700 (estimate) | | storage temp. | 2-8°C | | solubility | chloroform: 20 mg/mL, clear, slightly yellow | | pka | 15.02±0.70(Predicted) | | form | Solid | | color | White to Pale Yellow | | Water Solubility | Soluble in chloroform (50 mg/ml), ethanol (83 mg/ml at 25°C), water (<1 mg/ml at 25°C), DMSO (<1 mg/ml at 25°C), and methanol. | | Merck | 14,3295 | | BRN | 94582 | | LogP | 6.602 (est) | | CAS DataBase Reference | 512-04-9(CAS DataBase Reference) | | NIST Chemistry Reference | Diosgenin(512-04-9) |
| | Diosgenin Usage And Synthesis |
| Chemical Properties | White to Off-White Dolid | | Uses | antiinflammatory, estrogen | | Uses | Aglicone of saponin dioscin. Diosgenin exists in some food supplements and herbal medicines and lowers plasma cholesterol by increasing fecal cholesterol excretion.
e and Progesterone. | | Uses | pregnenolone and progesterone precursor | | Definition | ChEBI: Diosgenin is a sapogenin that is spirostan which is substituted by a hydroxy group at the 3beta position, contains a double bond at the 5-6 position, and has R- configuration at position 25. A natural product found in Dioscorea (wild yam) species, it is used as the starting point for the commercial synthesis of a number of steroids, including cortisone, pregnenolone and progesterone. It has a role as an apoptosis inducer, an antiviral agent, an antineoplastic agent and a metabolite. It is a 3beta-sterol, a spiroketal, a hexacyclic triterpenoid and a sapogenin. It derives from a hydride of a spirostan. | | General Description | Diosgenin is a triterpene and a glycone derivative of dioscin. Yams, Trigonella foenum-graecum and Costus speciosus are some of its source. | | Biochem/physiol Actions | Diosgenin induces apoptosis in colon cancer cell lines and induces apoptosis, cell cycle arrest and cyclooxygenase activity in osteosarcoma cells. It serves as a precursor in steroid drug production. Diosgenin is shown to promote cholesterol production by stimulating biliary excretion. It influences lipoxygenase induced human erythroleukemia cell line differentiation. | | Anticancer Research | It is a steroidal saponin and legumes and yams are the rich sources of it. It is a notoriousprecursor of several synthetic steroidal drugs. It suppresses growth of cells andinduces apoptosis in human osteosarcoma, colon cancer, and leukemia. Its anticancermechanism is by arresting the cell cycle, disrupting the calcium homeostasis,activating p53, releasing apoptosis inducing factors, and modulating caspase-3activity. It suppresses NF-κB activation induced by TNF as a result of DNA binding,IκBα kinase activation, degradation, phosphorylation, p65 nuclear translocation,and phosphorylation. It suppresses proliferation and invasion and induces apoptosisby downregulation of cFLIP, cyclin-D1, TRAF1, COX-2, c-myc, Bfl-1/A1, BclxL,IAP1, Bcl-2, and MMP-9 (Aggarwal et al. 2008; Raju and Mehta 2008). | | Purification Methods | Crystallise diosgenin from acetone, and chromatograph it on Al2O3 and elute with *C6H6/Et2O (9:1), then recrystallise it from MeOH. Its solubility is ~4% in H2O and 5% in CHCl3. The acetate crystallises from AcOH with m 198o; and has [] D 20 -119o (pyridine). [Marker et al. J Am Chem Soc 65 1199 1943. Mazur et al. J Am Chem Soc 82 5889 1960, Beilstein 19 IV 862.] |
| | Diosgenin Preparation Products And Raw materials |
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