Troxerutin

Troxerutin Property

Melting point:

181°C

Boiling point:

1058.4±65.0 °C(Predicted)

Density 

1.65±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

Freely soluble in water, slightly soluble in ethanol (96 per cent) and practically insoluble in methylene chloride.

form 

Solid

pka

5.92±0.40(Predicted)

color 

Light Yellow to Yellow

Merck 

14,9789

BRN 

4778232

InChI

InChI=1/C33H42O19/c1-14-23(38)26(41)28(43)32(49-14)48-13-21-24(39)27(42)29(44)33(51-21)52-31-25(40)22-17(37)11-16(45-7-4-34)12-20(22)50-30(31)15-2-3-18(46-8-5-35)19(10-15)47-9-6-36/h2-3,10-12,14,21,23-24,26-29,32-39,41-44H,4-9,13H2,1H3/t14-,21+,23-,24+,26+,27-,28+,29+,32+,33-/s3

InChIKey

KMPBUGGPUQOWMJ-NXPSPVSKSA-N

SMILES

O([C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)O1)O)C1C(C2=C(C=C(OCCO)C=C2OC=1C1C=CC(OCCO)=C(OCCO)C=1)O)=O |&1:1,2,3,5,7,10,12,14,16,18,r|

CAS DataBase Reference

7085-55-4(CAS DataBase Reference)

Safety

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

LK8331500

HS Code 

2938100000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

Troxerutin Chemical Properties,Usage,Production

Chemical Properties

Yellow Powder

Originator

Venoruton,Novartis Co

Uses

vasoprotectant

Uses

Troxerutin, a derivative of the naturally occurring bioflavonoid rutin, is thought to inhibit red cell and platelet aggregation, improve erythrocyte deformability, and improve plasma viscosity retinal microcirculation. A double-blind randomized clinical trial compared troxerutin with placebo in 27 patients with CRVO. The limitations of the study included a small number of patients and short follow-up time.

Uses

Used in the treatment of venous disorders

Manufacturing Process

In a nitrogen atmosphere 120 g of caustic soda (3 moles) in solution are added to 610 g of rutin (1 mol) suspended in 2 litres of water, the mixture being vigorously agitated by a mechanical stirrer, 241.5 g of ethylene chlorohydrin being then introduced at 55°C for 10 min. When all the chlorohydrin has been thus added the temperature is progressively raised to 75°C and maintained at this level for 2 hours. After cooling, in a nitrogen atmosphere, the pH value adjusted to 5 by the addition of dilute hydrochloric acid. The solution is kept in an ice box for 24 hours and then filtered to remove any impurities. At reduced pressure the solution is evaporated until dry, the residue taken up in 3 litres of boning methanol which dissolves the tri-(β-hydroxyethyl)rutin formed and leaves the sparingly soluble sodium chloride behind. The tri-(β-hydroxyethyl)rutin is recovered from its methanolic solution either by evaporation and refrigeration, or by evaporation precipitation with absolute ethanol. In either case tri-(β-hydroxyethyl)rutin obtained is in the form of small very hygroscopic crystals which contain alcohol of crystallization.These crystals are quickly shaken washed in a little cold absolute ethanol and then dried in vacuum at 100°C. 680 g of anhydrous tri-(β-hydroxyethyl)rutin are thus obtained in the form of a yellow powder which melts at 156°C.GB Patent No. 833,174; April 21, 1960; Assigned to Zyma S.A., a Swiss Corporation, of Route Etraz, Nyon Canton of Vaud, Switzerland

Therapeutic Function

Topical venotonic

Biological Activity

Troxerutin is a brain penetrant, vasoprotective flavonol isolated from Sophora japonica, which is present in many other plants including grains, fruits, and vegetables. Troxerutin exhibits multiple biological activities including anti-oxidative, anti-radiation, and anti-inflammatory. Recent study indicates th at troxerutin improves the synaptic failure induced by Aβ peptide. It appears th at Troxerutin could promote radioprotection by stimulating NEAT1 to upregulate PDPK1 expression by suppressing miR-147.

target

VEGFR | Wnt/β-catenin | NF-kB | SOD | PI3K | Akt

References

[1] Patent: CN104478972, 2017, B. Location in patent: Paragraph 0018; 0019; 0020; 0021; 0022; 0023; 0024-0031
[2] Patent: CN106892950, 2017, A. Location in patent: Paragraph 0018-0026
[3] Chinese Chemical Letters, 2013, vol. 24, # 3, p. 223 - 226
[4] Patent: CN103601772, 2016, B. Location in patent: Paragraph 0011-0014
[5] Patent: CN104447914, 2017, B. Location in patent: Paragraph 0013; 0014