Vitamin P

Base Information

• Chemical Name: Vitamin P
• CAS No.: 153-18-4
• Molecular Formula: C27H30O16
• Molecular Weight: 610.526
• Hs Code.: 29381000
• European Community (EC) Number: 215-672-2
• NSC Number: 408168,9220
• DSSTox Substance ID: DTXSID70859300
• Wikidata: Q27163468
• Metabolomics Workbench ID: 130886
• ChEMBL ID: CHEMBL32579
• Mol file: 153-18-4.mol

Synonyms:3',4',7-trihydroxyethylrutin;3',4',7-tris(O-(2- hydroxyethyl))rutin;oxerutin;Paroven;Posorutin;Relvene;Rhéoflux;Teboven;Troxérutine Mazal;troxerutin;Troxerutin-ratiopharm;Troxeven;Vastribil;Veinamitol;Veniten retard;Veno SL;Venorutin;venoruton;venoruton P4;Venotrulan Trox;vitamin P4

Chemical Property of Vitamin P

Chemical Property:

• Appearance/Colour: pale-yellow crystalline solid
• Melting Point: 195 °C (dec.)(lit.)
• Refractive Index: 1.765
• Boiling Point: 983.1 °C at 760 mmHg
• PKA: 6.17±0.40(Predicted)
• Flash Point: 325.4 °C
• PSA: 269.43000
• Density: 1.827 g/cm³
• LogP: -1.68710
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: pyridine: 50 mg/mL
• Water Solubility.: 12.5 g/100 mL
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 6
• Exact Mass: 610.15338487
• Heavy Atom Count: 43
• Complexity: 1020

Purity/Quality:

99%, ^*data from raw suppliers

Rutin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O
• Recent EU Clinical Trials: Resolution Enhancement by a Supplemental Open-Label Venoactive drug for Eight weeks in Deep Vein Thrombosis
• Chemical Structure and Properties: Rutin is a rutinoside derived from quercetin, with glucose and rhamnose sugar groups attached to the hydroxy group at position C-3. It is classified as a flavonol glycoside and is found in various plants, including buckwheat, tobacco, forsythia, hydrangea, and viola.; Rutin is known for its antioxidant properties and its ability to decrease capillary fragility.
• Therapeutic Properties: Rutin is considered a natural flavonoid compound with various therapeutic potentials. It has antiplatelet, antiviral, and antihypertensive properties.; Rutin strengthens the capillaries of blood vessels due to its high radical scavenging activity and antioxidant capacity. Its therapeutic properties include antioxidant, anti-inflammatory, neuroprotective, and cardioprotective activities.
• Neuroprotective Effects: Rutin has demonstrated neuroprotective effects in conditions such as brain ischemia, hypoxia, glutamate, and oxidative stress. It attenuates ischemic neural apoptosis, reduces lipid peroxidation, and enhances endogenous antioxidant defense enzymes.; Rutin also reduces neuroinflammation and exhibits neuroprotective effects in animal models.
• Anti-inflammatory Effects: Rutin suppresses the activity of proinflammatory cytokines by reducing TNF-伪 and IL-1尾 production in microglia.
• Modulation of Hypercholesterolemia: Rutin acts as a selective and non-toxic modulator of hypercholesterolemia. In studies conducted on animal models, rutin significantly reduced plasma triglyceride levels and total cholesterol levels.
• Sources: Rutin was first discovered in buckwheat and is considered a major dietary source of this compound. It is widely distributed in vegetables and fruits, contributing to its consumption as part of a healthy diet. Buckwheat, in particular, is rich in rutin and has been found to prevent oxidative damage and exhibit antihypertensive effects.

Technology Process of Vitamin P

There total 6 articles about Vitamin P 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:

quercetin 3-O-<β-D-apiofuranosyl(1->2)α-L-rhamnopyranosyl(1->6)>-β-D-glucopyranoside) → D-apiose (639-97-4,6477-44-7,42927-70-8) + rutin (153-18-4)

Guidance literature:

With trifluoroacetic acid;

DOI:10.1016/0031-9422(93)85134-D

Reference yield:

pasta seca → isoquercetin (482-35-9) + quercetol (117-39-5,74893-81-5) + rutin (153-18-4)

Guidance literature:

With ammonium bicarbonate; In acetic acid methyl ester; water; at 45 ℃; for 0.75h; Purification / work up;

Reference yield:

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 6-O-{6-deoxy-2-O-[(4-hydroxy-3,5-dimethoxyphenyl)carbonyl]-α-L-mannopyranosyl}-β-D-glucopyranoside → rutin (153-18-4)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 1h;

DOI:10.1002/hlca.201000043

upstream raw materials:

N,N,N',N'-tetramethyl-para-phenylenediamine

Downstream raw materials:

2-(3,4-Diethoxy-phenyl)-5,7-diethoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-chromen-4-one

3''-O-butanoylrutin

(2S,3R,4S,5R,6R)-2-((5,7-diacetoxy-2-(3,4-diacetoxyphenyl)-4-oxochroman-3-yl)oxy)-6-(((2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyltetrahydro-2H-pyran-3,4,5-triyl triacetate

troxerutin

Refernces

• 1、 -. "READILY WATER-SOLUBLE ISOQUERCITRIN COMPOSITION". . . Retrieved 2012/04/11.
• 2、 -. "Recovery of isoquercetin from bioflavanoid pastes". Page column 3-4. . Retrieved 2008/06/13.