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CAS

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Troxerutin, a derivative of the naturally occurring bioflavonoid rutin, is a pharmaceutical compound with various therapeutic properties. It is known for its ability to inhibit red cell and platelet aggregation, improve erythrocyte deformability, and enhance plasma viscosity and retinal microcirculation.

7085-55-4

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7085-55-4 Usage

Uses

Used in Venous Disorders Treatment:
Troxerutin is used as a treatment for venous disorders, particularly chronic venous insufficiency and varicose veins. It helps to improve the symptoms and reduce the complications associated with these conditions.
Used as a Vasoprotectant:
Troxerutin serves as a vasoprotectant, which means it helps to protect blood vessels from damage and maintain their integrity. This property makes it useful in preventing and treating various vascular-related issues.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Troxerutin is used as an active ingredient in various formulations, such as tablets, capsules, and injections, for the treatment of venous disorders and as a vasoprotectant.
Used in Clinical Trials:
Troxerutin has been the subject of clinical trials to evaluate its efficacy in treating specific conditions, such as central retinal vein occlusion (CRVO). A double-blind randomized clinical trial compared troxerutin with a placebo in 27 patients with CRVO, although the study had limitations, including a small number of patients and a short follow-up time.

Originator

Venoruton,Novartis Co

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

Check Digit Verification of cas no

The CAS Registry Mumber 7085-55-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,0,8 and 5 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 7085-55:
(6*7)+(5*0)+(4*8)+(3*5)+(2*5)+(1*5)=104
104 % 10 = 4
So 7085-55-4 is a valid CAS Registry Number.
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?/m0/s1

7085-55-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name TROXERUTIN

1.2 Other means of identification

Product number -
Other names POSORUTIN

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:7085-55-4 SDS

7085-55-4Synthetic route

oxirane
75-21-8

oxirane

rutin
153-18-4

rutin

troxerutin
7085-55-4

troxerutin

Conditions
ConditionsYield
With chitosan In methanol at 75℃; for 3h; Concentration; Temperature; Autoclave;96%
With natural polymer sodium alginate In methanol at 70℃; for 4h; Temperature; Autoclave;87.6%
Stage #1: oxirane; rutin With sodium hydroxide In water at 75℃; for 6h;
Stage #2: With hydrogenchloride In water pH=4;
rutin
153-18-4

rutin

2-bromoethanol
540-51-2

2-bromoethanol

troxerutin
7085-55-4

troxerutin

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80 - 85℃;94.9%
rutin
153-18-4

rutin

2-chloro-ethanol
107-07-3

2-chloro-ethanol

troxerutin
7085-55-4

troxerutin

Conditions
ConditionsYield
With potassium hydroxide at 68℃; for 24h; Temperature; Inert atmosphere;90%
With potassium carbonate In N,N-dimethyl-formamide for 0.133333h; Heating;
oxirane
75-21-8

oxirane

7-mono-O-(β-hydroxyetyl)rutoside
23869-24-1

7-mono-O-(β-hydroxyetyl)rutoside

troxerutin
7085-55-4

troxerutin

Conditions
ConditionsYield
With pyridine In methanol at 75 - 80℃; Reagent/catalyst; Temperature; Autoclave;64%
With sodium hydroxide In methanol; water at 60 - 70℃; Reagent/catalyst; Solvent;
oxirane
75-21-8

oxirane

rutin
153-18-4

rutin

A

7,3',4'-trihydroxyethylisoquercitrine-3-glucoside
266363-39-7

7,3',4'-trihydroxyethylisoquercitrine-3-glucoside

B

7,5',4'-trihydroxyethylisoquercitrine-3-glucoside

7,5',4'-trihydroxyethylisoquercitrine-3-glucoside

C

7,4'-dihydroxyethylkaempferol-3-rutinoside
791084-12-3

7,4'-dihydroxyethylkaempferol-3-rutinoside

D

7,4'-di-hydroxyethyl rutoside
13190-91-5

7,4'-di-hydroxyethyl rutoside

E

troxerutin
7085-55-4

troxerutin

F

5,7,3',4'-tetra-hydroxyethyl rutoside
6980-20-7

5,7,3',4'-tetra-hydroxyethyl rutoside

Conditions
ConditionsYield
With sodium hydroxide In water at 75℃; for 6h; Product distribution / selectivity;
troxerutin
7085-55-4

troxerutin

3',4'-bis(2-O-sulfate ethoxy)-7-(2-O-sulfate ethoxy)rutin

3',4'-bis(2-O-sulfate ethoxy)-7-(2-O-sulfate ethoxy)rutin

Conditions
ConditionsYield
Stage #1: troxerutin With triethylamine sulfurtrioxide In N,N-dimethyl acetamide at 20 - 100℃; for 0.5h; Microwave irradiation;
Stage #2: With triethylamine In N,N-dimethyl acetamide at 4℃; for 24h;
Stage #3: With sodium acetate In water
89%
glutaric acid divinyl ester
10355-47-2

glutaric acid divinyl ester

troxerutin
7085-55-4

troxerutin

troxerutin vinyl glutarate
1218941-80-0

troxerutin vinyl glutarate

Conditions
ConditionsYield
With pyridine at 50℃; for 72h; Enzymatic reaction;65%
With pyridine; alkaline protease from Bacillus subtilis at 50℃; for 120h; Enzymatic reaction; regioselective reaction;
divinyl adipate
4074-90-2

divinyl adipate

troxerutin
7085-55-4

troxerutin

troxerutin vinyl adipate
1218941-81-1

troxerutin vinyl adipate

Conditions
ConditionsYield
With pyridine at 55℃; for 96h; Enzymatic reaction;60%
With pyridine; alkaline protease from Bacillus subtilis at 50℃; for 120h; Enzymatic reaction; regioselective reaction;
azelaic acid divinyl ester
10355-49-4

azelaic acid divinyl ester

troxerutin
7085-55-4

troxerutin

troxerutin vinyl azelate
1218941-82-2

troxerutin vinyl azelate

Conditions
ConditionsYield
With pyridine at 60℃; for 148h; Enzymatic reaction;57%
With pyridine; alkaline protease from Bacillus subtilis at 50℃; for 120h; Enzymatic reaction; regioselective reaction;
acetic anhydride
108-24-7

acetic anhydride

troxerutin
7085-55-4

troxerutin

3',4',7-tri-O-(2-acetoxyethoxy)quercetin
1429915-87-6

3',4',7-tri-O-(2-acetoxyethoxy)quercetin

Conditions
ConditionsYield
With sulfuric acid at 20℃; for 7h;57%
divinyl sebacate
10355-50-7

divinyl sebacate

troxerutin
7085-55-4

troxerutin

troxerutin vinyl sebacate
1218941-83-3

troxerutin vinyl sebacate

Conditions
ConditionsYield
With pyridine at 60℃; for 120h;55%
With pyridine; alkaline protease from Bacillus subtilis at 50℃; for 120h; Enzymatic reaction; regioselective reaction;
dodecandioic acid divinyl ester

dodecandioic acid divinyl ester

troxerutin
7085-55-4

troxerutin

troxerutin vinyl dodecandiate

troxerutin vinyl dodecandiate

Conditions
ConditionsYield
With pyridine at 50℃; for 96h;51%
troxerutin
7085-55-4

troxerutin

3,5-Dihydroxy-3',4',7-tri-(β-hydroxyethoxy)flavon
23077-88-5

3,5-Dihydroxy-3',4',7-tri-(β-hydroxyethoxy)flavon

Conditions
ConditionsYield
With hydrogenchloride In methanol Heating; Yield given;
divinyl tridecanedioate
15423-11-7

divinyl tridecanedioate

troxerutin
7085-55-4

troxerutin

C48H66O22
1218941-84-4

C48H66O22

Conditions
ConditionsYield
With pyridine; alkaline protease from Bacillus subtilis at 50℃; for 120h; Enzymatic reaction; regioselective reaction;
divinyl butanedioate
13416-90-5

divinyl butanedioate

troxerutin
7085-55-4

troxerutin

C39H48O22
1218941-79-7

C39H48O22

Conditions
ConditionsYield
With pyridine; alkaline protease from Bacillus subtilis at 50℃; for 120h; Enzymatic reaction; regioselective reaction;
dodecandioic acid divinyl ester

dodecandioic acid divinyl ester

troxerutin
7085-55-4

troxerutin

C54H71NO21

C54H71NO21

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 96 h / 50 °C
2: 1-octyl-3-methyl-3H-imidazolium nitrate / 48 h / 60 °C
View Scheme
divinyl adipate
4074-90-2

divinyl adipate

troxerutin
7085-55-4

troxerutin

C50H63NO23

C50H63NO23

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 96 h / 55 °C / Enzymatic reaction
2: N-octylpyridinium tetrafluoroborate / 24 h / 60 °C
View Scheme
divinyl sebacate
10355-50-7

divinyl sebacate

troxerutin
7085-55-4

troxerutin

C54H71NO23

C54H71NO23

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 120 h / 60 °C
2: n-butylpyridinium chloride / 36 h / 70 °C
View Scheme
troxerutin
7085-55-4

troxerutin

C46H57NO21

C46H57NO21

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 72 h / 50 °C / Enzymatic reaction
2: 1-octyl-3-methylimidazolium tetrafluoroborate / 24 h / 50 °C
View Scheme
troxerutin
7085-55-4

troxerutin

C46H56FNO21

C46H56FNO21

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 72 h / 50 °C / Enzymatic reaction
2: 1-octyl-3-methyl-imidazolium bromide / 24 h / 50 °C
View Scheme
troxerutin
7085-55-4

troxerutin

C45H55NO21

C45H55NO21

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 72 h / 50 °C / Enzymatic reaction
2: 1-hexyl-3-methylimidazolium tetrafluoroborate / 24 h / 50 °C
View Scheme
troxerutin
7085-55-4

troxerutin

C47H57NO21

C47H57NO21

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 72 h / 50 °C / Enzymatic reaction
2: 1-octyl-3-methyl-imidazolium bromide / 24 h / 60 °C
View Scheme
troxerutin
7085-55-4

troxerutin

C48H59NO23

C48H59NO23

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 72 h / 50 °C / Enzymatic reaction
2: 1-octylpyridinium bis[(trifluoromethyl)sulfonyl]amide / 30 h / 60 °C
View Scheme
troxerutin
7085-55-4

troxerutin

C52H67NO22

C52H67NO22

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 148 h / 60 °C / Enzymatic reaction
2: N-n-hexylpyridinium tetrafluoroborate / 36 h / 60 °C
View Scheme

7085-55-4Relevant articles and documents

Troxerutin compound

-

Paragraph 0050-0052; 0061-0065, (2020/01/14)

The invention discloses a troxerutin compound prepared by using an advanced on-line process control technology. The troxerutin compound is measured by X-ray powder diffraction, and a X-ray powder diffraction pattern expressed by a 2 diffraction angle shows characteristic diffraction peaks at the 2 of 8.15+/-0.2 degrees, 9.24+/-0.2 degrees, 12.31+/-0.2 degrees, 17.10+/-0.2 degrees, 17.92+/-0.2 degrees, 18.73+/-0.2 degrees and 23.45+/-0.2 degrees. The compound has the characteristics of high purity, low impurity content, good fluidity and good stability.

Preparation method of high-content troxerutin

-

Paragraph 0028; 0030-0031; 0034-0035; 0038-0039; 0042-0043, (2018/09/08)

The invention discloses a preparation method of high-content troxerutin and belongs to the technical field of pharmaceutical chemistry. The preparation method is characterized in that the preparationmethod of high-content troxerutin comprises the following steps: carrying out acetylation and purification of crude rutin used as a raw material, then hydrolyzing the crude rutin to obtain high-content rutin with a content being higher than 99.0%; reacting the high-content rutin under the catalysis action of a catalyst which is a third-generation PAMAM dendrimer to prepare troxerutin; and purifying the troxerutin to obtain the high-content troxerutin with a content being higher than 99.0%. According to the method, the high-quality rutin with the content being higher than 99.0% is used as the raw material, so that the high-content troxerutin crude drug is prepared; the method is low in cost and simple and convenient in steps, is economical and environmentally friendly, and is suitable for industrial production; the content of the prepared troxerutin can reach 99.0% or above.

A self-priming stirred autoclave preparation of troxerutin method

-

Paragraph 0018; 0019; 0020; 0021; 0022; 0023; 0024-0031, (2017/06/29)

The invention discloses a method for preparing troxerutin by adopting a self-suction type stirred autoclave. The method comprises the following steps: adding raw materials namely rutin, ethylene oxide, a solvent namely methanol and a catalyst namely natural weakly-alkaline high-molecular compound chitosan into a self-suction type stirred autoclave, starting a digital control instrument, setting a temperature to be 70-90 DEG C, regulating a voltage to be 100V, setting a rotating speed to be 1000r/min, stirring and heating to reach a set temperature, and reacting for 3-6 hours; and stopping stirring after reaction is ended, rapidly cooling by using cold water, shutting down the digital control instrument, opening a reaction kettle, pouring out reaction liquid, adjusting a pH value of the poured reaction liquid to be 5-6 by using hydrochloric acid, performing suction filtration, adding a crystal seed into the reaction liquid subjected to suction filtration, standing for later crystallization, and filtering to obtain a product namely troxerutin. According to the method disclosed by the invention, the reaction raw materials are integrally added into the self-suction type stirred autoclave, so that material feeding steps can be simplified; and the adopted catalyst is natural weakly-alkaline high-molecular compound chitosan, so that the raw material is wide in source, and is natural, non-toxic and weakly-alkaline, and side reactions such as hydrolysis, oxidation and the like caused by strong alkaline catalysis can be avoided.

Preparation method of high-content troxerutin

-

Paragraph 0018-0026, (2017/07/19)

The invention discloses a preparation method of high-content troxerutin and belongs to the technical field of medicinal chemistry. According to the technical scheme, the preparation method of the high-content troxerutin comprises the specific steps that a coarse raw material product rutin is purified and refined to obtain high-content rutin higher than 99.0%; the high-content rutin reacts under the catalytic action of a catalyst natural polymer sodium alginate to prepare troxerutin; the troxerutin is purified to obtain the high-content troxerutin with the content higher than 98.0%. The preparation method refines the raw material rutin, water is adopted as a solvent in the refining process, the method is green and environmentally friendly, and the purity of the obtained rutin can be up to 99.0% or above. In addition, during troxerutin preparation, the natural polymer sodium alginate and appropriate reaction condition are adopted to make reaction reach the best level, and the high-content troxerutin crude drug with content higher than 98.0% can be obtained only by simply purifying the obtained product.

A high-purity of troxerutin preparation method

-

Paragraph 0013; 0014, (2017/07/01)

The invention discloses a preparation method of high-purity troxerutin. According to the preparation method of the high-purity troxerutin, the synthesis and refining processes of the troxerutin are improved; sodium methoxide or sodium ethoxide is selected as a catalyst, supercritical CO2 is selected for extraction and crystallization refining of the troxerutin, and finally, the troxerutin of which the yield and the purity both are greatly improved in contrast with a traditional process can be obtained.

High-purity troxerutin and preparation method thereof

-

Paragraph 0024; 0053-0059; 0062-0069; 0072-0079; 0083; 0084, (2017/08/29)

The invention provides high-purity troxerutin and a preparation method thereof, and relates to the technical field of medicinal chemistry and organic synthetic chemistry. The preparation method comprises a front etherification step, a complexation step, a post etherification step and a post-treatment step. The preparation method of the high-purity troxerutin is relatively low in cost, the high-purity troxerutin can be prepared and the method is suitable for industrial production.

Preparing method of 3',4',7'-troxerutin

-

Paragraph 0038; 0039, (2017/05/17)

The invention relates to a preparing method of 3',4',7'-troxerutin. The provided preparing method of 3',4',7'-troxerutin comprises the steps of mixing water and rutin at 10-30 DEG C, dropwise adding a catalyst potassium hydroxide solution under the condition of nitrogen protection stirring, slowly adding ethylene chlorohydrin, increasing the temperature to 60-70 DEG C, conducting a thermostatic reaction for 4-5 hours, and then adding potassium hydroxide to continue the reaction for 15-20 hours; the 3',4',7'-troxerutin is obtained after purification and refinement. The 3',4',7'-troxerutin prepared through the method is simple in production technology, and little oxidation hydrolysis by-product is generated, and the 3',4',7'-troxerutin is high in yield. By adopting water as a solution, purification solution formaldehyde can be recycled and utilized at the same time, thus the cost is sharply saved in large-scale production, meanwhile, the generation of waste materials is reduced, and economy and environmental friendliness of production is achieved.

Ultrasonic-assisted chemical synthesis Troxerution

-

Paragraph 0011-0014, (2017/01/23)

The invention relates to an ultrasonic-assisted synthetic method of troxerutin. Ultrasonic is used for organic chemical reactions in a new form of energy, so that many reactions which cannot be carried out or difficult to carry out in the past can be carried out smoothly; the ultrasonic is greatly superior to the traditional stirring and external heating methods as a convenient, quick, effective and safe synthetic technique. After the ultrasonic is used for synthesizing troxerutin, the reaction time is only 45min, in contrast, the reaction time of the traditional liquid phase method is 90-120min, therefore, the reaction time of the ultrasonic technique is reduced by half; besides, the reaction temperature is reduced by 30-40 DEG C, the etherification rate is increased by 20%, and the etherification rate can be 95%. Furthermore, the ultrasonic technique is simple in process and easy for industrial production.

PREPARATION METHOD OF TRIHYDROXYETHYL RUTOSIDE

-

Paragraph 0093; 0094, (2016/05/02)

The present invention relates to a preparation method of trihydroxyethyl rutoside. In the method, rutin is firstly prepared into 7-monohydroxyethyl rutoside with a purity of greater than or equal to 98% by weight, and then 7-monohydroxyethyl rutoside is hydroxyethylated to give troxerutin having less than 2% of non-hydroxyethylated rutoside derivatives. The amount of 7,3′,4′-trihydroxyethyl rutoside in troxerutin is more than 80% by weight. The product is further purified so that 7,3′,4′-trihydroxyethyl rutoside with a purity of greater than or equal to 98% by weight could be obtained.

PREPARATION METHOD OF TRIHYDROXYETHYL RUTOSIDE

-

Paragraph 0083; 0085; 0086, (2017/01/05)

The present invention refers to tree hydrocyethylmetacrylate base toe side relates to manufacturing method of (trihydroxyethyl rutoside), said method (rutin) routine first content is detected to be compared with a 98% or more 7- base toe side hydrocyethylmetacrylate mono (7-monohydroxyethyl rutoside) after prepared with, continues to 7-mono hydrocyethylmetacrylate of hydrocyethylmetacrylate for on base toe side non by performing a photo lithography process (hydroxyethylated) (-glycidyl) 2% impurities derivatives base toe side of hydrocyethylmetacrylate [...] be smaller than present, obtains and makes (troxerutin), during said [...] 7,3 ', 4' -80% hydroxyethyl base toe side weight content and present, said continues product 98% or more weight content which comprises purifying an 7,3 ', 4' -may yield an hydroxyethyl base toe side.

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