(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[10.8.0.02,9.04,8.013,18]icosan]-18'-en-16'-ol

• ChemBase ID: 72937
• Molecular Formular: C27H42O3
• Molecular Mass: 414.62058
• Monoisotopic Mass: 414.3133952
• SMILES: C1[C@@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3C[C@H]2[C@@H]1[C@@H]([C@]1(O2)CC[C@H](CO1)C)C)C)O
• Canonical SMILES: C[C@@H]1CC[C@@]2(OC1)O[C@@H]1[C@H]([C@@H]2C)[C@@]2([C@@H](C1)[C@@H]1CC=C3[C@]([C@H]1CC2)(C)CC[C@@H](C3)O)C
• 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/t16-,17+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1
• InChIKey: WQLVFSAGQJTQCK-VKROHFNGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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,^8.0^1^3,^1^8]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
• IUPAC Traditional name: diosgenin; nitogenin
• Synonyms: (25R)-5-Spirosten-3β-ol; 3β-Hydroxy-5-spirostene; Diosgenin; DHA; Diosgenin

Database IDs

• CAS Number: 512-04-9
• EC Number: 208-134-3
• MDL Number: MFCD00016887
• Beilstein Number: 94582
• PubChem SID: 24893501; 162037857
• PubChem CID: 99474
• CHEMBL: 412437
• Chemspider ID: 89870
• Unique Ingredient Identifier: K49P2K8WLX
• Wikipedia Title: Diosgenin

CALCULATED PROPERTIES

• Acid pKa: 18.20429
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.927305
• LogD (pH = 7.4): 4.927305
• Log P: 4.927305
• Molar Refractivity: 120.2659 cm^3
• Polarizability: 47.84818 Å^3
• Polar Surface Area: 38.69 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: chloroform: soluble20 mg/mL, clear, slightly yellow

Safety Information

• Storage Condition: -20°C
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... UGT1A4(54657)

Product Information

• Purity: ≥93%; ≥99.0% (TLC)
• Salt Data: Free Base
• Impurities: ≤4% water
• Empirical Formula (Hill Notation): C27H42O3

DETAILS

MP Biomedicals - 05212687

MP Biomedicals Rare Chemical collection

Selleck Chemicals - S2291

Research Area: Infection
Biological Activity:
Diosgenin is a steroid sapogenin and the precursor for the semisynthesis of progesterone which in turn was used in early combined oral contraceptive pills.It 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), diosgenin is used for the commercial synthesis of cortisone, pregnenolone, progesterone, and other steroid products. [1] Diosgenin also causes an inhibition of the growth of fibroblast-like synoviocytes from human rheumatoid arthritis, with apoptosis induction associated with cyclooxygenase-2 (COX-2) up-regulation. Celecoxib, a selective COX-2 inhibitor, provoked a large decrease in diosgenin-induced apoptosis even in the presence of exogenous prostaglandin E2, whereas interleukin-1β, a COX-2 inducer, strongly increased diosgenin-induced apoptosis of these synoviocytes. [2]

Sigma Aldrich - D1634

Biochem/physiol Actions
Diosgenin is a plant steroid which induces apoptosis in colon cancer cell lines and induces apoptosis, cell cycle arrest and COX activity in osteosarcoma cells.

REFERENCES

• Liagre B et al. Arthritis Res Ther. 2004;6(4):R373-83.