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[ CAS No. 62499-27-8 ] {[proInfo.proName]}

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Chemical Structure| 62499-27-8
Chemical Structure| 62499-27-8
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Product Details of [ 62499-27-8 ]

CAS No. :62499-27-8 MDL No. :MFCD00272169
Formula : C13H18O7 Boiling Point : -
Linear Structure Formula :- InChI Key :PUQSUZTXKPLAPR-UJPOAAIJSA-N
M.W : 286.28 Pubchem ID :115067
Synonyms :
Gastrodine

Calculated chemistry of [ 62499-27-8 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.54
Num. rotatable bonds : 4
Num. H-bond acceptors : 7.0
Num. H-bond donors : 5.0
Molar Refractivity : 66.72
TPSA : 119.61 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -9.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.27
Log Po/w (XLOGP3) : -1.41
Log Po/w (WLOGP) : -1.79
Log Po/w (MLOGP) : -1.48
Log Po/w (SILICOS-IT) : -0.85
Consensus Log Po/w : -0.85

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.68
Solubility : 59.2 mg/ml ; 0.207 mol/l
Class : Very soluble
Log S (Ali) : -0.6
Solubility : 71.9 mg/ml ; 0.251 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.04
Solubility : 259.0 mg/ml ; 0.904 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 4.1

Safety of [ 62499-27-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 62499-27-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 62499-27-8 ]

[ 62499-27-8 ] Synthesis Path-Downstream   1~39

  • 1
  • [ 64291-41-4 ]
  • [ 62499-27-8 ]
YieldReaction ConditionsOperation in experiment
93.03% With potassium hydroxide; In ethanol; for 4h;pH 9;Reflux; 4.98 mg of ethanol was added to 0.98 kg of acetylconrodin,Add potassium hydroxide to adjust and maintain the system rhoH- = 9, after 2h reaction to stop the reaction, concentrated to 2.4L, add 4.85L of ethanol, reflux reaction 2h after the reaction to stop the reaction with TLC concentration solution; The total volume of the solution is 3.23L, 0.5 times the volume of ethyl acetate is added to the concentrate, and the resulting solid is dried to obtain 0.59kg of the crude extract of gastrodin, the yield is 92.65%; the filtrate is the mother liquor b, A mixed solvent of ethanol and ethyl acetate in a ratio of (alcohol: ester = 1: 1 (v / v)): gastrodin = 8: 1 (V / W) was added to the crude 0.59 kg of gastrodin, The mixture is heated to completely dissolve; filter impurity, the filtrate cooling after precipitation of crystals, to obtain pure gastrodin 0.518kg, the yield of 87.80%; filtrate for the mother liquor C, recovery reserve;The crude liquid b and the mother liquor c concentrated, filtered and dried to obtain the crude extract of gastrodin 0.097kg; 0.097kg in the crude extract of paclitaxel by adding 0.39L methanol, the mixture heated to completely dissolve; filter impurity, the filtrate cooled after precipitation of crystals, Product gastrodin 0.087kg, the yield of 13.66%And finally get pure gastrodin 0.605kg, the total yield of 93.03%.
90% With methanol; sodium methylate; In water; at 20℃; for 5h;Inert atmosphere; Sodium methoxide (200muL, 1 M in MeOH) was added to a solution of 5 (9.92 g, 0.020 mol) in 100 mL dry methanolunder a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 5 hfollowed by neutralization with Amberlite IR 120(H+). Then the reaction mixture was filtered,and the resulting filtrate was evaporated to dryness under vacuum. Finally, recrystallization ofthe crude product from methanol-chloroform (1:8, V/V) yielded 5.21 g of the desired compound1 as white crystals. Yield: 90 %
55g With diethylamine; In methanol; for 2h;Reflux; After 300 g of ethyl acetate was put into the reactor, 50 g of potassium triacetoxyborohydride was put into the reactor,Then, 100 g of 4-formylphenyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside was charged,Temperature control in 20 to 30 insulation reaction,Samples were monitored by TLC,Reaction 1 hour reaction is complete,The reaction was quenched by adding the reaction solution to 300 ml of water,And then take the upper organic phase,The organic phase was concentrated to a solid under vacuum,Then, 300 g of methanol and 22 g of diethylamine were added and refluxed for 2 hours,Samples were monitored by TLC,After completion of the reaction, 10 g of activated carbon was added for 10 minutes,filter,The filtrate was concentrated to one third of the original volume,Then, 300 g of acetone was added to the reaction solution,Stirring crystallization for 1 hour,Filter the day linen temperature 70g,Dried at 70 Gastrodin dry goods 55g.The products obtained by testing the quality of the indicators are in line with national standards.The obtained product was subjected to HPLC chromatographic detection, The results are shown in Figure 1,Product purity of 99.9673%,The impurity content was 0.0327%.Purity above 99.9%Containing only one impurity below 0.1%Far below the pharmacopoeia standard.
  • 3
  • C35H46O15 [ No CAS ]
  • [ 62499-27-8 ]
  • [ 88675-13-2 ]
  • (1S,4aS,6S,7R,7aS)-6-Hydroxy-1-methoxy-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid [ No CAS ]
  • 4
  • (4aS,6S,7R,7aS)-6-Acetoxy-1-methoxy-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid 4-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-benzyl ester [ No CAS ]
  • [ 62499-27-8 ]
  • [ 88675-13-2 ]
  • (1S,4aS,6S,7R,7aS)-6-Hydroxy-1-methoxy-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid [ No CAS ]
  • 5
  • C43H54O18 [ No CAS ]
  • [ 62499-27-8 ]
  • 1-O-methyl-deoxyloganic acid aglycone [ No CAS ]
  • [ 88675-13-2 ]
  • (1S,4aS,6S,7R,7aS)-6-Hydroxy-1-methoxy-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid [ No CAS ]
  • 7
  • [ 572-09-8 ]
  • [ 62499-27-8 ]
  • 8
  • C35H46O14 [ No CAS ]
  • [ 62499-27-8 ]
  • 9
  • urceolatoside A [ No CAS ]
  • [ 62499-27-8 ]
  • 10
  • urceolatoside C [ No CAS ]
  • [ 62499-27-8 ]
  • 15
  • [ 1010838-87-5 ]
  • coelovirin E [ No CAS ]
  • [ 910884-04-7 ]
  • [ 62499-27-8 ]
  • 16
  • [ 1010838-88-6 ]
  • coelovirin E [ No CAS ]
  • [ 1010838-85-3 ]
  • [ 62499-27-8 ]
  • 17
  • [ 1010838-89-7 ]
  • coelovirin E [ No CAS ]
  • [ 1010838-85-3 ]
  • [ 62499-27-8 ]
  • 18
  • [ 1010838-90-0 ]
  • (-)-4-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyloxybenzyl alcohol [ No CAS ]
  • [ 62499-27-8 ]
  • [ 60192-20-3 ]
  • 19
  • [ 1010838-90-0 ]
  • [ 62499-27-8 ]
  • [ 256459-23-1 ]
  • 20
  • [ 1010838-91-1 ]
  • [ 62499-27-8 ]
  • [ 60192-20-3 ]
  • 21
  • [ 62499-27-8 ]
  • [ 1126638-80-9 ]
  • 22
  • [ 2280-44-6 ]
  • [ 623-05-2 ]
  • [ 15887-38-4 ]
  • [ 62499-27-8 ]
  • 24
  • [ 2887-07-2 ]
  • [ 62499-27-8 ]
YieldReaction ConditionsOperation in experiment
96.2% With sodium tetrahydroborate; sodium methylate; In methanol; at 50℃; To the methanol (400 g) was added 4-formylphenyl-2,3,4,6-O-tetraacetyl-beta-D-glucopyranoside (0.2 mol, 90.5 g) 3.0g), PH value was measured, the reaction was heated to 50 C for 7 hours, evaporated under reduced pressure to dry methanol and transesterification of methyl acetate, methanol (400g) was added, a small amount of sodium methylate to adjust the PH is alkaline, then slowly added Sodium borohydride (0.07 mol, 2.65 g) was detected by TLC. After the reaction was completed, activated carbon was decolored and the resulting metal salt such as sodium acetate was removed and concentrated to dryness under reduced pressure to give a white solid which was recrystallized from 95% Cycle applied many times) to give 55.1g of white crystalline solid gastrodin, yield 96.2%, melting point 154.5-155.5
63.5% With methanol; potassium borohydride; at 58℃; for 0.5h;Industrial scale; Example 6Take 1kg tetraacetyl. Add 3.5L anhydrous methanol. Heat to 58 C reflux. Add potassium borohydride then undergo reduction reaction. After reacting for 30 min. Take sample then add, dropwise, chromogenic agent. When ared color does not appear (if red color is still apparent, continue adding potassium borohydride to undergo reaction). Concentrate recovered anhydrous ethanol to concentrated solution 1L. Undergo thin liquid chromatography to determine reaction completion. Add 3L anhydrous ethanol. Concentrate to concentrated solution 2L. Undergo thin liquid chromatography to determine reaction completion. Add 4L anhydrous ethanol to concentrated solution 2L. Quench potassium borohydride using 20% aqueous sulfuric acid. Make the pH of the alcohol solution to pH 7. Allow to stand for 8h. Eliminate precipitated solids. Concentrate to separate out gastrodin. Stop concentration. Allow concentrated solution to stand for 8h at room temperature to crystallize. Crumble bulk solids, dry, obtain 0.635 kg gastrodin. The gastrodin underwent tests to be in line with the national standard. In terms of tetraacetyl, mass yield 63.5%, molar yield 97.3%.
  • 26
  • [ 59252-47-0 ]
  • [ 62499-27-8 ]
YieldReaction ConditionsOperation in experiment
96.5% With sodium methylate; In methanol; for 4h;Reflux; (3)The recrystallized compound 111 (10 (^, 0.186111001) was dissolved in 3501111 dry methanol,Add 208 sodium methoxide, reflux reaction 4 hours, add acetic acid to adjust the pH value to neutral, filter,The filtrate was concentrated to give 53 mg of gastrodin96.5%,
  • 27
  • pentaacetyl gastrodin [ No CAS ]
  • [ 62499-27-8 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; In methanol; at 40℃; for 1.5h; (32) into the salt, adding 40. 91kg of pentaetyl gastrodin and 130kg of methanol together into a third reaction tank, heating to 40 C with stirring, and then adding the sodium methoxide solution prepared in the step (31) to the third reaction tank, At 40 C under the insulation reaction 1. 5h
  • 28
  • [ 62499-27-8 ]
  • [ 57-13-6 ]
  • 4-(hydroxymethyl)phenyl-β-D-glucopyranoside urea salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 5 - 60℃; for 1h; 2.86 g of <strong>[62499-27-8]gastrodin</strong> was dissolved in 20 mL of ethanol, 0.6 g of urea was added, heated to 60 C., stirred at 60 C. for 60 min and then cooled to 5 C. After completion of the reaction, filtration was carried out and the resulting solid was washed with ethanol, dried, Collect the solid.After testing,The solid obtained in this example is <strong>[62499-27-8]gastrodin</strong> and urea eutectic compound,
  • 29
  • [ 62499-27-8 ]
  • [ 64-19-7 ]
  • [ 64291-41-4 ]
YieldReaction ConditionsOperation in experiment
86% Take tetraacetyl 60g, 360ml of methanol was added, stirring was started, the temperature dropped to below 5.0 , potassium borohydride was added 3.6g, the reaction temperature was controlled at 8.0 for 45 minutes after the reaction. Add glacial acetic acid, adjust the pH to 5.0-6.0, continue to stir for 5 minutes, add medicinal charcoal 1.0g, stir at room temperature for 20 minutes and then filter. Add the filtrate to 2L purified water and stir at 5C.The crystals were crystallized in minutes, filtered, washed, and dried under reduced pressure at 70C to obtain crude acetylated <strong>[62499-27-8]gastrodin</strong>.Process backYield 86%, chromatographic purity 98.9%.
  • 30
  • [ 50-99-7 ]
  • [ 62499-27-8 ]
  • 31
  • [ 604-68-2 ]
  • [ 62499-27-8 ]
  • 32
  • [ 105-38-4 ]
  • [ 62499-27-8 ]
  • C16H22O8 [ No CAS ]
  • C19H26O9 [ No CAS ]
  • 33
  • parishin J [ No CAS ]
  • [ 623-05-2 ]
  • [ 62499-27-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; for 0.25h;pH 5.25; General procedure: Proper amount of fresh RGE slices were ground in a mortar. The pH value of fresh RGE juicewas 5.25 measured by pH meter. The above 10 monomer compounds were precisely weighed 1.0 mg, dissolved by 1.0 mL hydrochloric acid solution of pH 5.25, and placed in a vial. The sample solution of 1.0 mg/mL was obtained. The vials of 10 samples were steamed in the steamer simulating the steaming process of RGE. The timing started after the round vapor. After 15 min, the vials were taken out. After cooling to room temperature, the analysis was carried out under the condition of Section 3.5, PA was analyzed by HPLC-ESI-TOF/MS and the other nine compounds were analyzed by HPLC.
  • 34
  • 3-hydroxy-5-oxo-5-[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methoxy]-3-[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methoxycarbonyl]pentanoic acid [ No CAS ]
  • [ 623-05-2 ]
  • [ 952068-57-4 ]
  • [ 952283-93-1 ]
  • [ 62499-27-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; for 0.25h;pH 5.25; General procedure: Proper amount of fresh RGE slices were ground in a mortar. The pH value of fresh RGE juicewas 5.25 measured by pH meter. The above 10 monomer compounds were precisely weighed 1.0 mg, dissolved by 1.0 mL hydrochloric acid solution of pH 5.25, and placed in a vial. The sample solution of 1.0 mg/mL was obtained. The vials of 10 samples were steamed in the steamer simulating the steaming process of RGE. The timing started after the round vapor. After 15 min, the vials were taken out. After cooling to room temperature, the analysis was carried out under the condition of Section 3.5, PA was analyzed by HPLC-ESI-TOF/MS and the other nine compounds were analyzed by HPLC.
  • 35
  • parishin C [ No CAS ]
  • [ 623-05-2 ]
  • [ 952068-57-4 ]
  • [ 62499-27-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; for 0.25h;pH 5.25; General procedure: Proper amount of fresh RGE slices were ground in a mortar. The pH value of fresh RGE juicewas 5.25 measured by pH meter. The above 10 monomer compounds were precisely weighed 1.0 mg, dissolved by 1.0 mL hydrochloric acid solution of pH 5.25, and placed in a vial. The sample solution of 1.0 mg/mL was obtained. The vials of 10 samples were steamed in the steamer simulating the steaming process of RGE. The timing started after the round vapor. After 15 min, the vials were taken out. After cooling to room temperature, the analysis was carried out under the condition of Section 3.5, PA was analyzed by HPLC-ESI-TOF/MS and the other nine compounds were analyzed by HPLC.
  • 36
  • parishin K [ No CAS ]
  • parishin J [ No CAS ]
  • [ 62499-27-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; for 0.25h;pH 5.25; General procedure: Proper amount of fresh RGE slices were ground in a mortar. The pH value of fresh RGE juicewas 5.25 measured by pH meter. The above 10 monomer compounds were precisely weighed 1.0 mg, dissolved by 1.0 mL hydrochloric acid solution of pH 5.25, and placed in a vial. The sample solution of 1.0 mg/mL was obtained. The vials of 10 samples were steamed in the steamer simulating the steaming process of RGE. The timing started after the round vapor. After 15 min, the vials were taken out. After cooling to room temperature, the analysis was carried out under the condition of Section 3.5, PA was analyzed by HPLC-ESI-TOF/MS and the other nine compounds were analyzed by HPLC.
  • 37
  • [ 62499-28-9 ]
  • [ 623-05-2 ]
  • [ 952068-57-4 ]
  • [ 952283-93-1 ]
  • [ 62499-27-8 ]
  • 3-hydroxy-5-oxo-5-[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methoxy]-3-[[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methoxycarbonyl]pentanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; for 0.25h;pH 5.25; General procedure: Proper amount of fresh RGE slices were ground in a mortar. The pH value of fresh RGE juicewas 5.25 measured by pH meter. The above 10 monomer compounds were precisely weighed 1.0 mg, dissolved by 1.0 mL hydrochloric acid solution of pH 5.25, and placed in a vial. The sample solution of 1.0 mg/mL was obtained. The vials of 10 samples were steamed in the steamer simulating the steaming process of RGE. The timing started after the round vapor. After 15 min, the vials were taken out. After cooling to room temperature, the analysis was carried out under the condition of Section 3.5, PA was analyzed by HPLC-ESI-TOF/MS and the other nine compounds were analyzed by HPLC.
  • 38
  • [ 77162-64-2 ]
  • [ 623-05-2 ]
  • [ 62499-27-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In water; for 0.25h;pH 5.25; General procedure: Proper amount of fresh RGE slices were ground in a mortar. The pH value of fresh RGE juicewas 5.25 measured by pH meter. The above 10 monomer compounds were precisely weighed 1.0 mg, dissolved by 1.0 mL hydrochloric acid solution of pH 5.25, and placed in a vial. The sample solution of 1.0 mg/mL was obtained. The vials of 10 samples were steamed in the steamer simulating the steaming process of RGE. The timing started after the round vapor. After 15 min, the vials were taken out. After cooling to room temperature, the analysis was carried out under the condition of Section 3.5, PA was analyzed by HPLC-ESI-TOF/MS and the other nine compounds were analyzed by HPLC.
  • 39
  • [ 62499-27-8 ]
  • [ 623-05-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; beta-D-glucosidase; In water; at 35℃; for 2h;pH 5.25;Enzymatic reaction; GAS (0.591 mg/mL) and beta-D-glucosidase (1.24 mg/mL) were dissolved in hydrochloric acidsolution of pH 5.25 in a vial. Two copies of the above samples were prepared. One was steamed on a steamer for 15 min, and the other was incubated in water bath at 35 C for 2 h. A 10 L aliquot was injected for HPLC analysis.
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