1.0 2010-04-08 22:10:20 UTC 2026-09-19 20:24:14 UTC FDB012734 Diosgenin Diosgenin is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Diosgenin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Diosgenin can be found in a number of food items such as carrot, wild carrot, yam, and bitter gourd, which makes diosgenin a potential biomarker for the consumption of these food products. Diosgenin, a phytosteroid sapogenin, is the product of hydrolysis by acids, strong bases, or enzymes of saponins, extracted from the tubers of Dioscorea wild yam, such as the Kokoro. The sugar-free (aglycone) product of such hydrolysis, diosgenin is used for the commercial synthesis of cortisone, pregnenolone, progesterone, and other steroid products . (25R)-Spirost-5-en-3β-ol (25R)-Spirost-5-en-3b-ol «delta&raquo 22α-Spirost-5-en-3β-ol 25d-Spirost-5-en-3b-ol 5,20a,22a,25D-spirosten-3β-ol 5,20alpha,22alpha,25D-Spirosten-3 beta-ol Dioscorea sapogenin Diosgenin Nitogenin Spirost-5-en-3-ol Spirost-5-en-3-ol deriv. Spirost-5-en-3-ol, (3β,25R)- Spirost-5-en-3-ol, (3b,25R)- Spirost-5-en-3α-Spirost-5-en-3β-ol Spirost-5-en-3β-ol, (25R)- Spirost-5-en-3b-ol, (25R)- C27H42O3 414.6206 414.31339521 (1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-en-16'-ol (1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-en-16'-ol 512-04-9 CC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CO1 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 WQLVFSAGQJTQCK-UHFFFAOYSA-N belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Triterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Triterpenoids Aliphatic heteropolycyclic compounds 3-beta-hydroxy delta-5-steroids 3-beta-hydroxysteroids Cyclic alcohols and derivatives Delta-5-steroids Hydrocarbon derivatives Ketals Oxacyclic compounds Oxanes Secondary alcohols Spirostanes and derivatives Tetrahydrofurans 3-beta-hydroxy-delta-5-steroid 3-beta-hydroxysteroid 3-hydroxy-delta-5-steroid 3-hydroxysteroid Acetal Alcohol Aliphatic heteropolycyclic compound Cyclic alcohol Delta-5-steroid Hydrocarbon derivative Hydroxysteroid Ketal Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Secondary alcohol Spirostane skeleton Steroid Tetrahydrofuran Triterpenoid 3beta-sterol Spirostan and derivatives Spirostanols and derivatives hexacyclic triterpenoid sapogenin spiroketal spirostan logp 4.15 ALOGPS logs -5.88 ALOGPS solubility 5.52e-04 g/l ALOGPS melting_point Mp 204-207° logp 4.93 ChemAxon pka_strongest_acidic 18.2 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac (1'S,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R,16'S)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-18'-en-16'-ol ChemAxon average_mass 414.6206 ChemAxon mono_mass 414.31339521 ChemAxon smiles CC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CO1 ChemAxon formula C27H42O3 ChemAxon inchi 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 ChemAxon inchikey WQLVFSAGQJTQCK-UHFFFAOYSA-N ChemAxon polar_surface_area 38.69 ChemAxon refractivity 120.27 ChemAxon polarizability 50.68 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon 495816 Asparagus Type 1 specific Asparagus officinalis 4686 Bitter gourd Type 1 specific Momordica charantia 3673 Carrot Type 1 specific Daucus carota ssp. sativus 79200 570.0 570.0 570.0 mg/100 g Fenugreek Type 1 specific Trigonella foenum-graecum 78534 1115.0 1115.0 1115.0 mg/100 g Wild carrot Type 1 specific Daucus carota 4039 570.0 570.0 570.0 mg/100 g Yam Type 1 specific Dioscorea 4672 Flavonol synthase/flavanone 3-hydroxylase Q41452 FLS_SOLTU Mitochondrial-processing peptidase subunit alpha Q10713 PMPCA Anti carcinogenic 161 A substance that inhibits or prevents the proliferation of neoplasms. Anti neoplastic 465 A substance that inhibits or prevents the proliferation of neoplasms. Anti peroxidative 520 Anti-cancer 159 A substance that inhibits or prevents the proliferation of neoplasms. Anti-diabetic 228 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-fatigue 274 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-inflammatory 370 A substance that reduces or suppresses inflammation. Anti-oxidant 502 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. Anti-proliferative 548 Anti-stress 632 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-viral 689 A substance that destroys or inhibits replication of viruses. Antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. Cardioprotective 769 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. Cytotoxic 859 A role played by the molecular entity or part thereof which causes the development of a pathological process. Estrogenic 922 Hepatoprotective 981 Any compound that is able to prevent damage to the liver. Hypocholesterolemic 1016 Hypolipidemic 1020 Immunosuppressant 1033 An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response. Inhibitor 1432 A substance that diminishes the rate of a chemical reaction. Insulin-Secretagogue 1465 Mastogenic 1092