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Chemical Structure| 50656-75-2 Chemical Structure| 50656-75-2

Structure of 50656-75-2

Chemical Structure| 50656-75-2

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Product Details of [ 50656-75-2 ]

CAS No. :50656-75-2
Formula : C10H8O5
M.W : 208.17
SMILES Code : O=C1C=CC2=C(O1)C=C(OC)C(O)=C2O

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Application In Synthesis of [ 50656-75-2 ]

* 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 [ 50656-75-2 ]

[ 50656-75-2 ] Synthesis Path-Downstream   1~1

  • 1
  • isofraxetin 6-O-β-D-glucopyranoside [ No CAS ]
  • [ 487-89-8 ]
  • [ 50656-75-2 ]
  • [ 55396-45-7 ]
  • [ 486-21-5 ]
  • [ 726-18-1 ]
  • [ 30567-87-4 ]
  • [ 22248-13-1 ]
  • [ 6935-99-5 ]
  • [ 20913-18-2 ]
  • 8'-dehydroxymethyl cleomiscosin A [ No CAS ]
  • [ 103-81-1 ]
  • [ 61281-37-6 ]
  • [ 66-22-8 ]
  • (+)-isoschizandrin [ No CAS ]
  • 6-methoxy-5′′-demethoxydaphneticin [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.9 mg; 1.3 mg; 1.1 mg; 0.8 mg; 5.9 mg; 2.0 mg; 1.0 mg; 2.1 mg; 2.3 mg; 1.1 mg; 1.1 mg; 0.9 mg; 1.1 mg; 1.2 mg; 1.7 mg With Angelica sinensis (Oliv.) Diels callus; In methanol; for 168.0h; General procedure: Isofraxetin-6-O-beta-D-glucopyranoside (859 mg) was dissolved in CH3OH (86.0 mL) and distributed into 59 bottles of the suspension cultures of A. sinensis callus equally. The mixture was co-cultured for 7 days, then the cells and medium were separated by filtration. The medium was concentrated to 200 mL and partitioned by the same volume of EtOAc (ethylacetate) and n-BuOH (n-butyl alcohol) successively for three times. Next, the organic phase was collected and concentrated under the reduced pressure toyield EtOAc extract (Fr. 1, 0.25 g) and n-BuOH extract (Fr. 2, 1.20 g) respectively. The cells were dried under 50C, and then were extracted in an ultrasonic bath with CH3OH for 30 min. After that, the extract was further partitioned by EtOAc and n-BuOH respectively to afford EtOAc extract (Fr. 3,0.62 g) and n-BuOH extract (Fr. 4, 1.46 g). Compared with the experimental group, cultures and medium without isofraxetin-6-O-b-D-glucopyranoside act as control group and was processed to get Fr. 5-8 by the same procedures. The combination of Fr. 1 and Fr. 3 (EE, 0.87 g) was subjected on ODS column chromatography (CC) with gradient elution CH3OH/H2O (from 0:100 to 100:0) to get five subfractions (Fr. 1a-5a). Next, Fr. 1a was separated by HPLC with ODS column (250 mm 10 mm, flow rate 3 mL/min) eluted with CH3OH/H2O(49: 51) to afford compounds 5 (2.1 mg, tR = 14 min), 6 (2.3 mg, tR = 18 min)and 3 (5.9 mg, tR = 39 min). Fr. 2a was firstly fractioned by silica gel CC(3 50 cm) with gradient elution petroleum/acetone (0:100-100:0) to get substraction 2a-1 and 2a-2. Then Fr. 2a-1 was purified by HPLC with ODS column (250 mm 10 mm, flow rate 3 mL/min) with CH3CN/H2O (37: 63) to provide compounds 8 (1.0 mg, tR = 22 min), 10 (1.1 mg, tR = 27 min) and 14(1.2 mg, tR = 35 min). While compound 15 (0.9 mg, tR = 25 min) was purifiedfrom substration Fr. 2a-2, using HPLC with ODS column (250 mm 10 mm,flow rate 3 mL/min) eluted with CH3CN/H2O (39: 61). And Fr. 3a was chromatographied on HPLC with ODS column (250 mm 10 mm, flow rate3 mL/min) to yield compounds 9 (1.1 mg, tR = 40 min) and 11 (0.9 mg,tR = 56 min) using CH3OH/H2O (35: 65) as elute. However, compounds 12(0.8 mg, tR = 37 min) and 13 (1.3 mg, tR = 49 min) were obtained from Fr. 4a byHPLC with ODS column (250 mm 10 mm, flow rate 3 mL/min) using CH3CN/H2O (8:92) as eluting solvent. Equally, Fr. 2 and Fr. 4 was combined as BE(2.66 g) to subject on ODS CC with CH3OH/H2O (from 0:100 to 100:0) to getseven fractions (Fr. 1b-7b). Fr. 1b was isolated using HPLC with ODS column(250 mm 10 mm, flow rate 3 mL/min) eluted by CH3OH/H2O (20: 80) andthen purified by Sephadex LH-20 chromatography eluted with CH3OH to afford compounds 1 (1.1 mg) and 2 (1.7 mg). Furthermore, compound 4 (2.0 mg) wasobtained from Fr. 3b by recrystallization in CH3OH. Next, Fr. 4b was subjectedon silica gel CC (3 50 cm) with gradient elution CH2Cl2/CH3OH (0:100-100:0)to get substraction Fr. 4b-1 and Fr. 4b-2. Then Fr. 4b-1 was purified by HPLCwith ODS column (250 mm 10 mm, flow rate 3 mL/min) with CH3CN/H2O(13: 87) to provide compounds 7 (1.1 mg, tR = 19 min) and 16 (1.8 mg,tR = 39 min).
 

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