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[ CAS No. 153-18-4 ]

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Chemical Structure| 153-18-4
Chemical Structure| 153-18-4
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Product Details of [ 153-18-4 ]

CAS No. :153-18-4 MDL No. :MFCD00006830
Formula : C27H30O16 Boiling Point : 983.1°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :610.52 g/mol Pubchem ID :5280805
Synonyms :

1. Rutin

Safety of [ 153-18-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 153-18-4 ]

  • Upstream synthesis route of [ 153-18-4 ]
  • Downstream synthetic route of [ 153-18-4 ]

[ 153-18-4 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 501-94-0 ]
  • [ 153-18-4 ]
  • [ 10338-51-9 ]
Reference: [1] ChemSusChem, 2017, vol. 10, # 9, p. 2040 - 2045
  • 2
  • [ 100-22-1 ]
  • [ 100-22-1 ]
  • [ 153-18-4 ]
Reference: [1] Journal of the Chemical Society. Perkin Transactions 2, 1996, vol. 0, # 11, p. 2497 - 2504
[2] Journal of the Chemical Society. Perkin Transactions 2, 1996, vol. 0, # 11, p. 2497 - 2504
  • 3
  • [ 75-21-8 ]
  • [ 153-18-4 ]
  • [ 7085-55-4 ]
YieldReaction ConditionsOperation in experiment
96% With chitosan In methanol at 75℃; for 3 h; Autoclave Weighing 30.53g (0.05 µM) Rutin, 2.42g (15mmol) catalyst natural alkaline high molecular compound chitosan, 100 ml methanol solvent and 15.4g (0.35 µM) ethylene oxide add to the sucking stirring in the autoclave, open the digital controller, the set temperature is 75 °C, the rotating speed of 1000r/min, stirring and heating to 75 °C, thermal insulation reaction 3h. After the reaction, the temperature rapidly in cold water, and the cessation of the stirring, the closing of the digital controller, open the reaction kettle, pouring the reaction solution. Pouring the reaction solution of hydrochloric acid for adjusting the pH 6, and filtering the catalyst, the reaction solution after filtering in a seed crystal standing crystallization, the obtained crystal 35.65g, yield 96percent, external standard content of 90.1percent.
87.6% With natural polymer sodium alginate In methanol at 70℃; for 4 h; Autoclave Take 200 g of rutin obtained in (1) and 10.0 g Natural polymer sodium alginate added to 400 g of anhydrous methanol, and then pass 100 g of ethylene oxide, sealed autoclave, heating and stirring began, heated to 70 ° C, incubated for 4.0 h, HPLC test Trihydroxyethyl rutin When the ratio reached 86percent, the reaction was quenched rapidly to terminate the reaction. Hydrochloric acid was added to adjust the pH value of the reaction solution to 6.0. After standing for crystallization for 12 h, the mixture was suction filtered and dried to obtain 198.4 g of solid with a yield of 99.2percent. 3) to190 g of the solid obtained in (2) was added to 3200 mL of a mixed solution of anhydrous methanol and ethanol (anhydrous methanol and BThe volume ratio of alcohol is 1 : 1), heated to reflux completely dissolved, add needle activated carbon 8.0 g, continue to reflow 0.5 h, while Hot filtration, The filtrate was allowed to stand at room temperature crystallization 12h after, Suction filtration, drying The product 166.4 g, yield 87.6percent, total yield 83.2percent, content 98.7percent.
116 g
Stage #1: With PAMAM dendrimer In methanol at 80℃; for 5 h;
Stage #2: Reflux
(2) Taking (1) obtained in the 145 g Rutin and 7.2 g 3 on behalf of the PAMAM dendritic polymer are added to the 580 g without water in methanol, then access 58 g ethylene oxide, sealing the high-pressure autoclave, the beginning of the heating and stirring, heated to 80 °C after, thermal insulation reaction 5.0 h, HPLC detection synthetizing Rutin proportion up to 86percent when, rapid cooling, the termination of the reaction, for adjusting the pH value of the reaction solution of hydrochloric acid for the 5.0, standing crystallization 12 h after, filtered, and dried to obtain a crystal 133 g, yield 91.7percent;(3) To the (2) obtained in the crystal 133 g by adding 2.5 L water-free methanol, heating to reflux to totally dissolve, adding active carbon 4.0 g, continue to reflux 1.0 h after, to take advantage of the heat filter, the filtrate is reduced to the room temperature is static devitrifying 12 h after, filtering, drying to obtain the product troxerutin 108 g, yield 81.2percent, total yield of 74.5percent, content 99.2percent.
Reference: [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
[6] Patent: CN106632548, 2017, A, . Location in patent: Paragraph 0024; 0053-0059; 0062-0069; 0072-0079; 0083; 0084
[7] Patent: CN108358987, 2018, A, . Location in patent: Paragraph 0028; 0030-0031; 0034-0035; 0038-0039; 0042-0043
  • 4
  • [ 153-18-4 ]
  • [ 107-07-3 ]
  • [ 7085-55-4 ]
YieldReaction ConditionsOperation in experiment
90% at 68℃; for 24 h; Inert atmosphere The reaction solvent water was dried at room temperature at 2000 kgInto the reaction tank,Then put rutin 610kg,Under nitrogen protection, the catalyst potassium hydroxide solution (containing 79 kg of potassium hydroxide)And then slowly added under the liquid surface249 kg of chloroethanol,Heating up to 68 ° C,Constant temperature reaction 4 hours and then add potassium hydroxide solution (containing potassium hydroxide 42kg),The reaction was continued for 20 hours after sampling,After the reaction was complete,Ice bath to 18 ° C,Under nitrogen protection, hydrochloric acid adjusts the pH to 6.The resulting solution was distilled under reduced pressure to dryness, and 4 times the weight of the obtained solidified methanol was stirred and heated to 75 ° C for 45 minutes. The crystals were cooled to 24 ° C for 12 hours and centrifuged to obtain 3 ', 4', 7 ' Trihydroxyethyl rutin crude, the resulting mother liquor into the distillation tank distillation, after passing the test apply. 3 ', 4', 7 'trihydroxyethyl rutin crude and ethyl acetate in the mass ratio of 1: 4 into the reaction tank, add activated carbon heated to 82 ° C, reflux 1 hour after the stop, the thermal filtration of the mother liquor cooling To 20 ° C for 10 hours,And then centrifugal rejection filter,Drying to produce 3 ', 4', 7-trihydroxyethyl rutin yield of 90percent, content of 91percent.
Reference: [1] Patent: CN106589017, 2017, A, . Location in patent: Paragraph 0038; 0039
[2] Archiv der Pharmazie, 1985, vol. 318, # 8, p. 747 - 753
  • 5
  • [ 75-21-8 ]
  • [ 153-18-4 ]
  • [ 266363-39-7 ]
  • [ 791084-12-3 ]
  • [ 13190-91-5 ]
  • [ 7085-55-4 ]
  • [ 6980-20-7 ]
Reference: [1] Patent: US6855697, 2005, B1, . Location in patent: Page/Page column 5; 6
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