(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编号: 72937
• 分子式: C27H42O3
• 平均质量: 414.62058
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: diosgenin; nitogenin
• 别名: (25R)-5-Spirosten-3β-ol; 3β-Hydroxy-5-spirostene; Diosgenin; DHA; Diosgenin

登记号

• CAS号: 512-04-9
• EC号: 208-134-3
• MDL号: MFCD00016887
• Beilstein号: 94582
• PubChem SID: 162037857; 24893501
• PubChem CID: 99474
• CHEMBL: 412437
• Chemspider ID: 89870
• 美国药典/FDA物质标识码: K49P2K8WLX
• 维基百科标题: Diosgenin

理论计算性质

• Acid pKa: 18.20429
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 4.927305
• LogD (pH = 7.4): 4.927305
• Log P: 4.927305
• 摩尔折射率: 120.2659 cm^3
• 极化性: 47.84818 Å^3
• 极化表面积: 38.69 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: chloroform: soluble20 mg/mL, clear, slightly yellow

安全信息

• 保存条件: -20°C
• 德国WGK号: 2
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 相关基因信息: human ... UGT1A4(54657)

产品相关信息

• 纯度: ≥93%; ≥99.0% (TLC)
• 成盐信息: Free Base
• 杂质: ≤4% water
• Empirical Formula (Hill Notation): C27H42O3

详细说明

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.

参考文献

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