398 JOURNAL OF CHEMICAL RESEARCH 2014
Experimental
1H), 9.49 (s, 1H), 7.54 (dd, J=8.6, 2.3 Hz, 1H), 7.42 (d, J=2.2 Hz, 1H),
7
.09 (d, J=8.6 Hz, 1H), 6.76 (s, 1H), 6.46 (d, J=2.1 Hz, 1H), 6.19 (d,
Scutellarin was obtained from Kunming Pharmaceutical Corporation
–
J=2.1 Hz, 1H), 3.85 (s, 3H); HRESI‑MS (m/z): 299.0547 for [M–H] ,
calcd 299.0556.
(
KPC) in Kunming, China. The sulfuric acid (98%, w/w) was of
analytical grade. The melting points were determined on an RY‑1
instrument which was uncorrected. IR spectra were recorded on a Bio‑
Rad FTS‑40 FT‑IR spectrometer. NMR experiments were conducted
on a Bruker Avance DRX 500 spectrometer or a Bruker Avance III 400
at 298 K, and the ESI‑MS data were recorded on an Agilent 6210 mass
spectrometer or a Bruker MicrOTOF Q‑II mass spectrometer.
This study was financially supported by Natural Science
Foundation of Yunnan Province (No. 2011FZ059, to X. Liao)
and National Natural Science Foundation of China (Nos.
21062009 and 21362016, to B. Yang). The authors thank KPC
for kind donation of scutellarin, and the editor for suggestions
on the hydrolysis mechanism.
Typical hydrolysis procedure (for entry 3, Table 1)
Sulfuric acid (2.0 mL, 0.037 mmol) was added dropwise to a beaker
(
100 mL) containing scutellarin (50 mg, 0.11 mmol). It was shaken
Received 12 February 2014; accepted 7 May 2014
Paper 1402462 doi: 10.3184/174751914X14017253941699
Published online: 12 July 2014
or agitated by ultrasound agitated to dissolve the substrate in the
acid at room temperature. Water (2.0 mL) was then added carefully
dropwise. When the evolution of heat ceased (in 10 minutes), the
mixture was added to water (15 mL) in one portion with stirring with
a glass rod. The yellow crystals that were deposited were collected
by suction filtration and washed by water (5 mL). In most cases, such
products were pure enough for direct use. Moreover, it could be further
purified by recrystallisation from aqueous methanol (70%, v/v) or
column chromatography on silica gel (eluent:ethyl acetate/formic
acid/water=100/4/3, v/v/v, R s of SCU and SCUE were 0.1 and 0.8 on
silica gel GF254 respectively). Light yellow crystals were obtained after
recrystallisation (28.5 mg, 93% yield); m.p. 285–287 °C (>300 °C) .
IR (KBr, cm ): ν 3442, 3331, 3098, 1671, 1619, 1587, 1509. H NMR
References
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(dd, J=10.8, 4.0 Hz, 2H), 7.58 (m, 3H), 6.94 (s, 1H), 6.62 (s, 1H).
2
5
Diosmetin (11): Yellow powder; yield 85%; m.p. 256–258 °C
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4
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1437, 1259; H NMR (500 MHz, DMSO‑d ): δ 12.93 (s, 1H), 10.87 (s,
6
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