Pharmakon1600-01503219

Base Information

• Chemical Name: Pharmakon1600-01503219
• CAS No.: 520-27-4
• Molecular Formula: C28H32O15
• Molecular Weight: 608.553
• Hs Code.: 29381000
• NSC Number: 758417
• ChEMBL ID: CHEMBL3039392
• Mol file: 520-27-4.mol

Synonyms:Spectrum_001563;Spectrum2_000858;Spectrum3_001571;Spectrum4_000168;Spectrum5_001243;BSPBio_003102;KBioGR_000655;KBioSS_002043;DivK1c_000671;SPECTRUM1503219;SPBio_000875;CHEMBL3039392;HMS502B13;KBio1_000671;KBio2_002043;KBio2_004611;KBio2_007179;KBio3_002602;NINDS_000671;HMS1922K03;Pharmakon1600-01503219;CCG-40091;NSC758417;AKOS015894942;SDCCGMLS-0066662.P001;IDI1_000671;NCGC00178296-01;SBI-0051790.P002;AB00052329_02;BRD-K91548452-001-03-0

Chemical Property of Pharmakon1600-01503219

Chemical Property:

• Appearance/Colour: Greyish-yellow or light yellow hygroscopic powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 277-278 °C
• Refractive Index: 1.711
• Boiling Point: 926.8 °C at 760 mmHg
• PKA: 6.10±0.40(Predicted)
• Flash Point: 305.2 °C
• PSA: 238.20000
• Density: 1.68 g/cm³
• LogP: -1.08970
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, soluble in dimethyl sulfoxide, practically insoluble in alcohol. It dissolves in dilute solutions of alkali hydroxides.
• Water Solubility.: Soluble in DMSO (50 mg/ml), water (122 mg/ml at 25°C), and ethanol (<1 mg/ml at 25°C).
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 7
• Exact Mass: 608.17412031
• Heavy Atom Count: 43
• Complexity: 995

Purity/Quality:

Diosmin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-36/37-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC(=C(C=C5)OC)O)O)O)O)O)O)O)O
• Isomeric SMILES: C[C@@H]1[C@H]([C@@H]([C@@H]([C@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC(=C(C=C5)OC)O)O)O)O)O)O)O)O
• Description: Diosmin was separated from the root of Scrophularia nodosa L. in 1925. The root of Scrophularia nodosa L. has the function of nourishing, reducing fever, relieving internal heat, and detoxicating. It was firstly recorded in the Shen Nong’s Classic of Materia Medica, as a class of middle-grade drug and is currently recorded in the Ch.P 2015, Volume I. The natural resource was abundant in China, mainly provided from Zhejiang, Sichuan, Hubei, Anhui, and Jiangsu provinces. In the clinical practice, Scrophularia nodosa L. was employed to eliminate pathogenic heat from the blood. In the clinical indication, diosmin was mainly applied to treat fever, polydipsia, maculitis, gingivitis, amygdalitis, laryngopharyngitis, acute lymphadenitis, etc. It also has the biological function of antiplatelet aggregation and antitumor. The chemical components include iridoids, phenylpropanoid glycoside, flavonoids, and fatty acids.
• Physical properties: Appearance: Grayish yellow or light yellow hygroscopic powder. Solubility: Practically insoluble in water, soluble in dimethyl sulfoxide, practically insoluble in alcohol. It dissolves in dilute solutions of alkali hydroxides. Melting point: 277–278°C.
• Uses: Diosmin is an agonist of the aryl hydrocarbon receptor (AhR) and exhibits anti-proliferative and anti-inflammatory. It is used in the treatment of venous disease, i.e., chronic venous insufficiency (CVI) and hemorrhoidal disease (HD). Diosmin also reduces capillary hyperpermeability and expression of endothelial adhesion molecules (ICAM1, VCAM1). It effectively inhibits the P-glycoprotein (Pgp)-mediated efflux in cells.
• Indications: The clinical indications of diosmin are those symptoms related to venous-lymphatic dysfunction such as leg heaviness, pains, soreness, and swelling in the morning. Besides, the symptoms related to acute hemorrhoids could also be treated with diosmin.
• Therapeutic Function: Bioflavonoid
• Clinical Use: Diosmin was mainly used to treat diseases like chronic venous dysfunction, haemorrhoids, lymphedema, phlebeurysm, etc.

Technology Process of Pharmakon1600-01503219

There total 9 articles about Pharmakon1600-01503219 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

hesperidin (520-26-3) → diosmin (520-27-4)

Guidance literature:

With iodine; In pyridine; at 90 ℃; for 10h;

DOI:10.1002/ardp.19833160307

Reference yield: 81.96%

(2S)-7-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one (64726-90-5) → diosmin (520-27-4)

Guidance literature:

(2S)-7-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one; With pyridine; iodine; at 10 ℃; for 0.5h;

at 170 ℃; for 0.045h; under 7500.75 Torr; Temperature; Time;

Reference yield: 81.96%

→ diosmin (520-27-4)

Guidance literature:

With pyridine; iodine; at 10 ℃; for 0.5h; under 760.051 Torr;

at 170 ℃; for 0.045h; under 7500.75 Torr;

upstream raw materials:

hesperidin

(2R,3Ξ)-5-acetoxy-2-(3-acetoxy-4-methoxy-phenyl)-3-bromo-7-[O²,O³,O⁴-triacetyl-O⁶-(tri-O-acetyl-α-L-rhamnopyranosyl)-β-D-glucopyranosyloxy]-chroman-4-one

5-hydroxyheptaacetyldiosmin

(2S)-7-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one

Downstream raw materials:

3’,7-diallyloxy-5-hydroxy-4’-methoxyflavone

5-hydroxy-3',4',7-trimethoxyflavone

5,7-dihydroxy-3',4'-dimethoxy flavone

2-(3,4-dimethoxy-phenyl)-7-hydroxy-5-methoxy-chromen-4-one

Refernces

• 1、 Tsunekawa, Ryuji,Katayama, Kazuhiro,Hanaya, Kengo,Higashibayashi, Shuhei,Sugimoto, Yoshikazu,Sugai, Takeshi. "Synthesis of 5-Hydroxy-3′,4′,7-trimethoxyflavone and Related Compounds and Elucidation of Their Reversal Effects on BCRP/ABCG2-Mediated Anticancer Drug Resistance". . p. 210 - 220. Retrieved 2018/10/15.
• 2、 -. "Method for preparing green and economic diosmin". Paragraph 0040; 0041. . Retrieved 2016/10/17.