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Chemical Structure| 51938-32-0 Chemical Structure| 51938-32-0
Chemical Structure| 51938-32-0

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Schaftoside is a natural product isolated and purified from the herbs of Desmodium styracifolium (Osh.) Merr. with antioxidant and anticancer activities.

Synonyms: Apigenin 6-C-glucoside-8-C-arabinoside;Shaftoside;APIGENIN-6-GLUCOSIDE-8-ARABINOSIDE

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

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Product Details of Schaftoside

CAS No. :51938-32-0
Formula : C26H28O14
M.W : 564.49
SMILES Code : O=C1C=C(C2=CC=C(O)C=C2)OC3=C1C(O)=C([C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O4)C(O)=C3[C@H]5[C@H](O)[C@@H](O)[C@@H](O)CO5
Synonyms :
Apigenin 6-C-glucoside-8-C-arabinoside;Shaftoside;APIGENIN-6-GLUCOSIDE-8-ARABINOSIDE
English Name :5,7-Dihydroxy-2-(4-hydroxyphenyl)-6-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-8-((2S,3R,4S,5S)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)-4H-chromen-4-one
MDL No. :MFCD21333256

Safety of Schaftoside

Application In Synthesis of Schaftoside

* 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 [ 51938-32-0 ]

[ 51938-32-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ CAS Unavailable ]
  • [ 51938-32-0 ]
  • [ 50-99-7 ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid at 120℃; General procedure: Acid hydrolysis with TFA was performed in TFA (2 M) at 120°C. The hydrolysate was separated over polyamideusing the previously reported method [24]. The hydrolysis products of 1 contained isocytisoside (5) [6] and D-glucose;of 2, schaftoside (17) [17] and D-glucose; of 3, genkwanin-6-C-β-D-glucopyranoside-8-C-α-L-arabinopyranoside (16) [3],and D-glucose; of 4, isovitexin (15) [20], ferulic acid, D-glucose, and D-xylose.
  • 2
  • [ 54619-17-9 ]
  • [ 51938-32-0 ]
YieldReaction ConditionsOperation in experiment
90% With methanol; sodium methylate at 0℃; for 5h; 1.9; 2.8 (8) Synthesis of target compound: Intermediate compound 12 (1.63g, 1.66mmol)Dissolve in freshly prepared anhydrous methanol, add freshly prepared anhydrous sodium methoxide (1M) to the reaction solution dropwise at 0°C,Adjust pH=910, after 5h reaction,Acidic resin neutralizes Dowex 50W×8(H+),After filtering out the resin,Spin the reaction solution to dryness,Then wash the target product three times with dichloromethane (3*5mL),After removing the product solvent,The target product was obtained as a yellow solid (840 mg, 90%).
89% With sodium methylate In methanol at 20℃; 5.8 Synthesis of schaftoside (1) To a solution of 5 (14.58 g, 14.8 mmol) in dry CH3OH (300 mL, freshly distilled) was added sodium methoxide (1 M, freshly made) at room temperature. The pH of the solution was controlled around 9-10 with sodium methoxide. After completion, the mixture was neutralized with Dowex 50W×8 (H+) resin. The mixture was filtered and the organic layers were concentrated to afford Schaftoside (1) (7.44 g, 89%) as a yellowish solid. (Rotamers observed by 1H NMR and 13C NMR). [α]D20 +77.8 (c 1.0, MeOH), 1H NMR (400 MHz, DMSO-d6, 100 °C) δ 13.77 (1H, brs, OH-5), 10.13 (1H, brs, OH-7), 9.24 (1H, brs, OH-4'), 8.08 (2H, br d, H-2',6'), 6.94-6.92 (2H, d, J=8 Hz, H-3',5'), 6.76 (1H, s, H-3); 6-C-β-Glc: 4.74 (1H, d, J=9.8Hz, H-1"), 3.92 (1H, m, H-2"), 3.28 (1H, m, H-3"), 3.28 (1H, m, H-4"), 3.28 (1H,m, H-5"), 3.70, 3.54 (2×1H, 2×m, 6"-CH2); 8-C-α-Ara: 4.81 (1H, d, J=9.6 Hz, H-1‴), 4.09 (1H, br m, H-2‴), 3.53 (1H, m, H-3‴), 3.88 (1H, m, H-4‴), 3.93, 3.69 (2×1H, 2×m, 5‴-CH2); 13C NMR (125 MHz, DMSO-d6, 60 °C) δ101.9 (C-2),102.0 (C-3), 181.8 (C-4), 160.7 (C-5), 108.0 (C-6), 159.0 (C-7), 104.0 (C-8), 153.9 (C-9), 103.0 (C-10), 120.9 (C-1'), 161.0 (C-4'), 128.6 (C-2',6'), 115.6 (C-3',5'); 6-C-β-Glc: 73.1 (C-1"), 70.6 (C-2"), 78.2 (C-3"), 69.7 (C-4"), 80.9 (C-5"), 60.5 (C-6"); 8-C-α-Ara: 74.6 (C-1‴), 68.7 (C-2‴), 74.1 (C-3‴), 68.3 (C-4‴), 70.3 (C-5‴). HRMS (ESI) for C26H28O14Na [M+Na]+: calcd. 587.1371; found 587.1362.
 

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