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[ CAS No. 520-33-2 ] {[proInfo.proName]}

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Chemical Structure| 520-33-2
Chemical Structure| 520-33-2
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Product Details of [ 520-33-2 ]

CAS No. :520-33-2 MDL No. :MFCD00075646
Formula : C16H14O6 Boiling Point : -
Linear Structure Formula :- InChI Key :AIONOLUJZLIMTK-AWEZNQCLSA-N
M.W : 302.28 Pubchem ID :72281
Synonyms :
NSC 57654;(–)-3',5,7-Trihydroxy-4'-methoxyflavanone;Prestwick_908;YSO2;Hesperin;Hesperitin;(S)-Hesperetin;(–)-Hesperetin

Calculated chemistry of [ 520-33-2 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.19
Num. rotatable bonds : 2
Num. H-bond acceptors : 6.0
Num. H-bond donors : 3.0
Molar Refractivity : 78.06
TPSA : 96.22 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.24
Log Po/w (XLOGP3) : 2.6
Log Po/w (WLOGP) : 2.19
Log Po/w (MLOGP) : 0.41
Log Po/w (SILICOS-IT) : 2.08
Consensus Log Po/w : 1.91

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.62
Solubility : 0.0719 mg/ml ; 0.000238 mol/l
Class : Soluble
Log S (Ali) : -4.27
Solubility : 0.0162 mg/ml ; 0.0000537 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.53
Solubility : 0.0884 mg/ml ; 0.000292 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.22

Safety of [ 520-33-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 520-33-2 ]

* 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.

  • Upstream synthesis route of [ 520-33-2 ]
  • Downstream synthetic route of [ 520-33-2 ]

[ 520-33-2 ] Synthesis Path-Upstream   1~23

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Reference: [1] Bioscience, Biotechnology and Biochemistry, 2006, vol. 70, # 6, p. 1386 - 1394
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YieldReaction ConditionsOperation in experiment
65.4% With sulfuric acid In methanol at 60℃; for 7.5 h; General procedure: Compound 2 was synthesized by literature procedure.1 A mixture of 1 (3.5 g, 5.7 mmol) and H2SO4 (10 mL) in anhydrous CH3OH (280 mL) was stirred at 60°C for 7.5 h, ethyl acetate (1.2 L) was then added at 20°C . The solution was washed with H2O (420 mL), and dried (Na2SO4). Evaporation afforded pale-yellow powder. The crude product was dissolved in acetone (70 mL) and added dropwise (60 min) to a stirred mixture of H2O/acetic acid (150:1, 700 mL) at 95°C . The slurry was cooled to 45°C and the product filtered and dried in vacuo.
52.1% With sulfuric acid In ethanol for 7.5 h; Reflux Hesperidin 1.50 g (2.46 mmol) was added to 90 mL of absolute ethanol and 3 mL of concentrated sulfuric acid was added with vigorous stirring. The mixture was heated under reflux for 7.5 h.The reaction mixture was distilled off under reduced pressure. Most of the ethanol was distilled off under reduced pressure. The residue was poured into distilled water and extracted with ethyl acetate (3 x 90 mL). The extracts were combined and washed with distilled water until neutral. Ethyl acetate was distilled off, A yellow residue was obtained, and the crude product was recrystallized from ethanol / water.The yield was 52.1percent,
49% at 20℃; for 0.166667 h; General procedure: Sulfuric acid (2.0mL, 0.037mmol) was added dropwise to a beaker (100 mL) containing scutellarin (50 mg, 0.11 mmol). It was shaken 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 (70percent, v/v) or column chromatography on silica gel (eluent:ethyl acetate/formic acid/water=100/4/3, v/v/v, Rfs of SCU and SCUE were 0.1 and 0.8 on silica gel GF254 respectively). Light yellow crystals were obtained after recrystallisation (28.5mg, 93percent yield); m.p. 285–287°C (>300°C)27. IR (KBr, cm–1): νmax 3442, 3331, 3098, 1671, 1619, 1587, 1509. 1H NMR (500MHz, DMSO‑d6): δ 12.80 (s, 1H, 5‑OH), 10.48 (s, 1H, 7‑OH), 10.33 (s, 1H, 4′‑OH), 8.75 (s, 1H, 6‑OH), 7.92 (d, 2H, J=8.6Hz, C2′, C6′‑H), 6.92 (d, 2H, J=8.6Hz, C3′, C5′‑H), 6.75 (s, 1H, C3‑H), 6.58 (s, 1H, C8‑H). HR‑ESI‑MS (m/z): 309.0363 for [M+Na]+, calcd 309.0370.
0.13 mol With sulfuric acid In dimethyl sulfoxide at 100℃; for 2 h; 0.16mol hesperidin placed in the reaction vessel,Addition of 500 mL of DMSO gave a hydrolyzate.Then dropping 50mL concentrated sulfuric acid to adjust the pH of the hydrolyzate is 5,The reaction was further stirred at 100 ° C for 2 hours under magnetic stirring,Standing filtered to give a precipitate,Drying to obtain 0.13mol hesperetin.

Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 95 - 106
[2] Medicinal Chemistry Research, 2011, vol. 20, # 8, p. 1200 - 1205
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 23, p. 7194 - 7197
[4] Patent: CN105693682, 2016, A, . Location in patent: Paragraph 0024; 0025
[5] Journal of Chemical Research, 2014, vol. 38, # 7, p. 396 - 398
[6] Journal of Agricultural and Food Chemistry, 2008, vol. 56, # 14, p. 5550 - 5557
[7] Journal of Chemical Research, 2014, vol. 38, # 7, p. 443 - 446
[8] Advanced Synthesis and Catalysis, 2015, vol. 357, # 1, p. 107 - 117
[9] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 5, p. 1460 - 1465
[10] RSC Advances, 2017, vol. 7, # 84, p. 53385 - 53395
[11] Patent: CN106946835, 2017, A, . Location in patent: Paragraph 0064; 0078; 0080
[12] International Immunopharmacology, 2018, vol. 61, p. 82 - 91
  • 3
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  • [ 26184-96-3 ]
  • [ 520-33-2 ]
Reference: [1] Carbohydrate Research, 2012, vol. 347, # 1, p. 69 - 75
[2] Journal of Agricultural and Food Chemistry, 2011, vol. 59, # 20, p. 11238 - 11243
[3] Food Chemistry, 2012, vol. 134, # 4, p. 2338 - 2344
[4] Food Chemistry, 2011, vol. 127, # 2, p. 394 - 403
[5] Journal of Molecular Catalysis B: Enzymatic, 2016, vol. 130, p. 70 - 73
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YieldReaction ConditionsOperation in experiment
28% With water In dimethyl sulfoxide at 30℃; for 1 h; aq. buffer; Enzymatic reaction α-Rhamnosyl-β-glucosidase was incubated with the aromatic alcohol 1.8 mM 4-methylumbelliferone (4-MU) as acceptor and 1.8 mM hesperidin as rutinose donor. Thin layer chromatography (TLC) of the enzymatic reaction mixture gave a weak fluorescent spot (Rf = 0.72), similar to that of 4-MU-glucoside (4-MU-Glc, Rf = 0.80). The spot was found to be a glycoconjugate that, taking into account the enzyme mechanism,10 strongly suggested the synthesis of 4-MU-rutinoside (Fig. 2). The yield of transglycosylation was 28percent after the first hour of reaction at 30 °C (Fig. 3). Subsequently, the amount of transglycosylation product remained constant for at least 3 h, while the hydrolysis was shown to proceed up to completion. This behavior is in agreement with that observed for other glycosidase-catalyzed synthesis. Transglycosylation rate is usually higher than free sugar formation rate during the first stage of the reaction and, later on, transglycosylation product concentration reaches a plateau or diminishes because it acts as a substrate of the enzyme. [24] and [25] The increment of the reaction temperature up to the near-optimal for hydrolysis (60 °C) was shown to diminish the yield of 4-MU-rutinoside, probably by favoring the hydrolysis of the transglycosylation product. The highest yield was obtained for the acceptor donor ratio in the range 0.8-1:1 (data not shown).
Reference: [1] Carbohydrate Research, 2012, vol. 347, # 1, p. 69 - 75
  • 5
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Reference: [1] FEBS Letters, 2016, p. 2619 - 2628
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Reference: [1] Food Chemistry, 2011, vol. 127, # 2, p. 394 - 403
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Reference: [1] Patent: US4150038, 1979, A,
  • 8
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Reference: [1] Bioscience, biotechnology, and biochemistry, 2003, vol. 67, # 7, p. 1443 - 1450
  • 9
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Reference: [1] Patent: EP1891967, 2008, A1, . Location in patent: Page/Page column 6; 7
[2] Patent: EP1891967, 2008, A1, . Location in patent: Page/Page column 6; 7
  • 10
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Reference: [1] Bioscience, Biotechnology and Biochemistry, 2006, vol. 70, # 6, p. 1386 - 1394
  • 11
  • [ 67-56-1 ]
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Reference: [1] Carbohydrate Research, 2012, vol. 347, # 1, p. 69 - 75
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Reference: [1] Carbohydrate Research, 2012, vol. 347, # 1, p. 69 - 75
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Reference: [1] Carbohydrate Research, 2012, vol. 347, # 1, p. 69 - 75
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Reference: [1] Carbohydrate Research, 2012, vol. 347, # 1, p. 69 - 75
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Reference: [1] Carbohydrate Research, 2012, vol. 347, # 1, p. 69 - 75
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Reference: [1] Carbohydrate Research, 2012, vol. 347, # 1, p. 69 - 75
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Reference: [1] Carbohydrate Research, 2012, vol. 347, # 1, p. 69 - 75
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Reference: [1] Carbohydrate Research, 2012, vol. 347, # 1, p. 69 - 75
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Reference: [1] Journal of the Chemical Society, 1956, p. 632,634
[2] Journal of the Chemical Society, 1956, p. 632,634
[3] Nippon Kagaku Zasshi, 1958, vol. 79, p. 709,717[4] Chem. Zentralbl., 1959, vol. 130, p. 6808
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Reference: [1] Carbohydrate Research, 2000, vol. 328, # 2, p. 141 - 146
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Reference: [1] Process Biochemistry, 2011, vol. 46, # 12, p. 2330 - 2335
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Reference: [1] Synthesis, 2012, vol. 44, # 9, p. 1308 - 1314
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Reference: [1] Advanced Synthesis and Catalysis, 2013, vol. 355, # 9, p. 1817 - 1828
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