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[ CAS No. 4773-96-0 ] {[proInfo.proName]}

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Chemical Structure| 4773-96-0
Chemical Structure| 4773-96-0
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Product Details of [ 4773-96-0 ]

CAS No. :4773-96-0 MDL No. :
Formula : C19H18O11 Boiling Point : -
Linear Structure Formula :- InChI Key :AEDDIBAIWPIIBD-ZJKJAXBQSA-N
M.W : 422.34 Pubchem ID :5281647
Synonyms :
NSC 248870;Alpizarin;Aphloiol;Alpizarine;Chinonin;Hedysarid;Chinomin
Chemical Name :1,3,6,7-Tetrahydroxy-2-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-9H-xanthen-9-one

Safety of [ 4773-96-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4773-96-0 ]

* 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 [ 4773-96-0 ]

[ 4773-96-0 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 92631-83-9 ]
  • [ 24699-16-9 ]
  • [ 4773-96-0 ]
  • 2
  • [ 92631-82-8 ]
  • [ 149-91-7 ]
  • [ 4773-96-0 ]
  • 3
  • 6′-O-acetyl mangiferin [ No CAS ]
  • [ 4773-96-0 ]
  • 4
  • [ 4773-96-0 ]
  • [ 3542-72-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; recorcinol; In water; for 6.0h;Reflux; To a solution of <strong>[4773-96-0]mangiferin</strong> (300 mg, 0.710 mmol) in 3 N HCl(10 mL) was added resorcinol (117 mg, 1.06 mmol) at ambient temperature. The reactionmixture was refluxed for 6 h and then cooled to ambient temperature. The reaction mixturewas slowly quenched with saturated NaHCO3 solution and stirred for 30 min. Thebrown precipitate was collected by filtration, washed with H2O, and then concentrated invacuo. The residue was purified by flash column chromatography on silica gel (gradient50% EtOAc in n-hexane to only EtOAc) to afford 131 mg (71%) of the crude norathyriol.After recrystallization with ethanol, pure norathyriol was obtained as a yellowish solid,mp. >320C (decomp.). The NMR spectral data were identical with those reported8: 1HNMR (800 MHz, DMSO-d6) d 13.16 (s, 1 H), 10.76 (bs, 1H), 7.37 (s, 1H), 6.85 (s, 1H),6.31 (d, 1H, J D 2.1 Hz), 6.14 (d, 1H, J D 2.1 Hz); 13C NMR (800 MHz, DMSO-d6) d178.9, 164.7, 162.6, 157.3, 154.0, 150.9, 143.7, 111.8, 108.0, 102.6, 101.6, 97.7, 93.6;LR-MS (FABC) m/z 261 (MCHC); HR-MS (FABC) calcd for C13H9O6 (MCHC)261.0394; found: 261.0399.
With hydrogenchloride; recorcinol; In water; at 150℃; for 6.0h;Green chemistry; Mangiferin in 3N HCl (10 mL, sigma-aldrich) solution(300 mg, 0.71 mmol, Xian Lyphar Biotech) with resorcinol(1.06 mmol, 1.5 equiv, TCI) was added and heated to reflux (150 C.) for 6 hours.After cooling the refluxed solution to room temperature (25 C.), saturated sodium bicarbonate (NaHCO 3) solution was slowly added to neutralize the mixed solution.The mixed solution was stirred for 30 minutes, then filtered and the solids washed with water.The dried solid was vacuum dried to give brown crude norathiol(crude norathyriol, yield: 71%, 131 mg) was obtained.Crude noratiriol was added to ethyl acetate (10 mL), heated, stirred for 30 minutes, cooled to room temperature (25 C.), and filtered. The solid was washed several times with ethyl acetate, and then the filtrate was concentrated to give noraritol.
  • 6
  • [ 108-24-7 ]
  • [ 4773-96-0 ]
  • [ 4706-56-3 ]
YieldReaction ConditionsOperation in experiment
78% With iodine; at 130℃; for 0.25h;Microwave irradiation; Mangiferin (3, 0.2 g, 0.5 mmol) and iodine (0.009 g, 0.07 mmol) were mixed in acetic anhydride (7 mL) and the reaction was kept under MW irradiation (400 W), at 130 C, for 15 min. After cooling, a saturated solution of sodium thiosulfate was added to convert iodine (dark yellow) into iodide (yellow). The crude product was extracted with CH2Cl2 and the organic layer was extracted with a saturated solution of NaHCO3 twice, dried with anhydrous Na2SO4, and filtered. The solvent was evaporated under reduced pressure and the oil obtained was dissolved in ethyl acetate. A yellow solid was obtained with petroleum ether 60-80 C corresponding to1,3,6,7-tetra-O-acetyl-2-C-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-9H-xanthen-9-one (7) (0.294 g, 0.39 mmol, 78 % yield); mp 143-147 C (petroleum ether 60-80 C).
  • 7
  • [ 102-92-1 ]
  • [ 4773-96-0 ]
  • 2-β-D-glucopyranosyl-7-cinnamoyloxy-1,3,6-trihydroxy-9H-xanthen-9-one [ No CAS ]
  • 8
  • [ 77-78-1 ]
  • [ 4773-96-0 ]
  • 2-β-D-tetrahydroxyglucopyranosyl-3,6,7-trimethoxy-1-hydroxy-9H-xanthen-9-one [ No CAS ]
  • 9
  • [ 102-92-1 ]
  • [ 4773-96-0 ]
  • 2-β-D-glucopyranosyl-1,3,6,7-tetrahydroxy-9H-xanthen-9-one [ No CAS ]
  • 10
  • [ 102-92-1 ]
  • [ 4773-96-0 ]
  • 2-β-D-tetracinnamoylglucopyranosyl-7-cynnamoyloxy-1,3,6-trihydroxy-9H-xanthen-9-one [ No CAS ]
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