5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one

• ChemBase编号: 72938
• 分子式: C28H32O15
• 平均质量: 608.54468
• 单一同位素质量: 608.17412032
• SMILES: [C@@H]1([C@H]([C@@H](O[C@H]([C@@H]1O)C)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)Oc1cc2c(c(c1)O)c(=O)cc(o2)c1cc(c(cc1)OC)O)O)O)O)O)O
• Canonical SMILES: COc1ccc(cc1O)c1cc(=O)c2c(o1)cc(cc2O)O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C28H32O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-8,10,19,21-30,32-37H,9H2,1-2H3/t10-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1
• InChIKey: GZSOSUNBTXMUFQ-YFAPSIMESA-N

名称和登记号

名称

• IUPAC标准名: 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one
• IUPAC传统名: 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one; diosmin
• 别名: 3′,5,7-三羟基-4′-甲氧基黄酮 7-芸香糖甙; 地奥司明; Diosmetin 7-rutinoside; Daflon; Ven-Detrex; Salinigricoflavonoloside; Barosmin;; Diosmin; 3′,5,7-Trihydroxy-4′-methoxyflavone 7-rutinoside; Diosmin

登记号

• CAS号: 520-27-4
• EC号: 208-289-7
• MDL号: MFCD00009772
• PubChem SID: 24893763; 162037858
• PubChem CID: 5281613
• ATC码: C05CA03
• CHEMBL: 231884
• Chemspider ID: 4444932
• KEGG ID: D07858
• 美国药典/FDA物质标识码: 7QM776WJ5N
• 维基百科标题: Diosmin

理论计算性质

• Acid pKa: 8.475596
• 质子受体: 15
• 质子供体: 8
• LogD (pH = 5.5): -0.4434314
• LogD (pH = 7.4): -0.47794226
• Log P: -0.4429759
• 摩尔折射率: 142.3911 cm^3
• 极化性: 56.485394 Å^3
• 极化表面积: 234.29 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: false

分子性质

安全信息

• 保存条件: -20°C
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

药理学性质

• 生物活性机理: Reduces the expression of endothelial adhesion molecules (ICAM1, VCAM1), and inhibits the adhesion, migration, and activation of leukocytes at the capillary level.; This leads to a reduction in the release of inflammatory mediators, principally oxygen free radicals and prostaglandins (PGE2, PGF2a).

产品相关信息

• 纯度: ≥90% (HPLC); 90%
• 级别: analytical standard; technical grade
• 成盐信息: Free Base
• 杂质: ≤10% water
• 生物来源: Isol. from Zanthoxylum avicennae, Diosma crenulata and others, first isol. from parsley
• 有效期: (limited shelf life, expiry date on the label)
• 应用领域: Antihaemorrhagic; Bioflavonoid; Venotonic
• Empirical Formula (Hill Notation): C28H32O15

详细说明

Selleck Chemicals - S2292

Research Area: Cardiovascular Disease
Biological Activity:
Diosmin is a semisynthetic phlebotropic agent and a member of the flavonoid family.Diosmin prolongs the vasoconstrictor effect of norepinephrine on the vein wall, increasing venous tone, and therefore reducing venous capacitance, distensibility, and stasis. Diosmin increases the venous return and reduces venous hyperpressure present. Diosmin improves lymphatic drainage by increasing the frequency and intensity of lymphatic contractions, and by increasing the total number of functional lymphatic capillaries. Furthermore, diosmin with hesperidine decreases the diameter of lymphatic capillaries and the intralymphatic pressure. [1]

Sigma Aldrich - 245313

Biochem/physiol Actions
Citrus flavonoid. Modification of hesperidin. Studied for its chemopreventive properties, including anti-proliferative and anti-inflammatory.

Sigma Aldrich - 61386

Biochem/physiol Actions
Citrus flavonoid. Modification of hesperidin. Studied for its chemopreventive properties, including anti-proliferative and anti-inflammatory.

Sigma Aldrich - D3525

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Citrus flavonoid. Modification of hesperidin. Studied for its chemopreventive properties, including anti-proliferative and anti-inflammatory.

参考文献

• http://en.wikipedia.org/wiki/Diosmin
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 98C, (ir)
• Lovecy, A. et al., J.C.S., 1930, 817, (synth)
• Arthur, H.R. et al., J.C.S., 1956, 632, (Diosmin)
• Horowitz, R.M. et al., J.O.C., 1956, 21, 1184, (isol)
• Booth, A.N. et al., J. Biol. Chem., 1958, 230, 661, (metab)
• Rsler, H. et al., J.O.C., 1965, 30, 4346, (pmr)
• Plouvier, V., C. R. Hebd. Seances Acad. Sci. Ser. D, 1966, 263, 439, (isol, struct)
• Brieskorn, C.H. et al., Arch. Pharm. (Weinheim, Ger.), 1971, 304, 557, (isol)
• Wagner, H. et al., Tet. Lett., 1976, 1799, (cmr)
• Oustrin, J. et al., Arzneim.-Forsch., 1977, 27, 1688, (pharmacol)
• Le Quesne, P.W. et al., J.C.S. Perkin 1, 1978, 1572, (isol, uv, pmr)
• Itokawa, H. et al., Chem. Lett., 1982, 1, 49, (ms)
• Fujita, M. et al., Chem. Pharm. Bull., 1982, 30, 1151, (cmr)
• Martindale, The Extra Pharmacopoeia, 28th/29th edn., Pharmaceutical Press, 1982, 12667
• Voigtlnder, H.W. et al., Arch. Pharm. (Weinheim, Ger.), 1983, 316, 219, (synth)
• Voirin, B., Phytochemistry, 1983, 22, 2107, (uv)
• Rashid, M.A. et al., Fitoterapia, 1995, 66, 471, (Diosmin, pmr, cmr)
• Bergan, J.J. et al., Angiology, 2001, 52, S43-S47, (diosmin, rev)
• Garner, R.C. et al., J. Pharm. Sci., 2002, 91, 32-40, (diosmin, pharmacol)