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 ID: 72938
• Molecular Formular: C28H32O15
• Molecular Mass: 608.54468
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 Traditional name: 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
• Synonyms: Diosmetin 7-rutinoside; Daflon; Ven-Detrex; Salinigricoflavonoloside; Barosmin;; Diosmin; 3′,5,7-Trihydroxy-4′-methoxyflavone 7-rutinoside; Diosmin; 3′,5,7-三羟基-4′-甲氧基黄酮 7-芸香糖甙; 地奥司明

Database IDs

• CAS Number: 520-27-4
• EC Number: 208-289-7
• MDL Number: MFCD00009772
• PubChem SID: 24893763; 162037858
• PubChem CID: 5281613
• ATC CODE: C05CA03
• CHEMBL: 231884
• Chemspider ID: 4444932
• KEGG ID: D07858
• Unique Ingredient Identifier: 7QM776WJ5N
• Wikipedia Title: Diosmin

CALCULATED PROPERTIES

• Acid pKa: 8.475596
• H Acceptors: 15
• H Donor: 8
• LogD (pH = 5.5): -0.4434314
• LogD (pH = 7.4): -0.47794226
• Log P: -0.4429759
• Molar Refractivity: 142.3911 cm^3
• Polarizability: 56.485394 Å^3
• Polar Surface Area: 234.29 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: 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).

Product Information

• Purity: ≥90% (HPLC); 90%
• Grade: analytical standard; technical grade
• Salt Data: Free Base
• Impurities: ≤10% water
• Biological Source: Isol. from Zanthoxylum avicennae, Diosma crenulata and others, first isol. from parsley
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Antihaemorrhagic; Bioflavonoid; Venotonic
• Empirical Formula (Hill Notation): C28H32O15

DETAILS

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.

REFERENCES

• 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)