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[ CAS No. 158932-33-3 ] {[proInfo.proName]}

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Chemical Structure| 158932-33-3
Chemical Structure| 158932-33-3
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Product Details of [ 158932-33-3 ]

CAS No. :158932-33-3 MDL No. :MFCD03427692
Formula : C32H46O16 Boiling Point : -
Linear Structure Formula :- InChI Key :SBVBJPHMDABKJV-PGCJWIIOSA-N
M.W : 686.70 Pubchem ID :9917980
Synonyms :
Secoisolariciresinol Diglucoside;(R,R)-SDG;SDG;(R,R)-LGM2605
Chemical Name :(2R,2'R,3S,3'S,4S,4'S,5R,5'R,6R,6'R)-6,6'-(((2R,3R)-2,3-Bis(4-hydroxy-3-methoxybenzyl)butane-1,4-diyl)bis(oxy))bis(2-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol)

Calculated chemistry of [ 158932-33-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 48
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.62
Num. rotatable bonds : 15
Num. H-bond acceptors : 16.0
Num. H-bond donors : 10.0
Molar Refractivity : 164.05
TPSA : 257.68 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -10.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.36
Log Po/w (XLOGP3) : -0.67
Log Po/w (WLOGP) : -2.23
Log Po/w (MLOGP) : -3.19
Log Po/w (SILICOS-IT) : -0.66
Consensus Log Po/w : -0.88

Druglikeness

Lipinski : 3.0
Ghose : None
Veber : 2.0
Egan : 1.0
Muegge : 4.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -2.87
Solubility : 0.925 mg/ml ; 0.00135 mol/l
Class : Soluble
Log S (Ali) : -4.27
Solubility : 0.0371 mg/ml ; 0.000054 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -0.96
Solubility : 76.0 mg/ml ; 0.111 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 6.71

Safety of [ 158932-33-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 158932-33-3 ]

* 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 [ 158932-33-3 ]

[ 158932-33-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 2649536-99-0 ]
  • [ 158932-33-3 ]
  • [ CAS Unavailable ]
  • [ 933048-96-5 ]
  • [ 933048-87-4 ]
  • [ 933048-91-0 ]
YieldReaction ConditionsOperation in experiment
In methanol; water at 60℃; for 4h;
  • 2
  • [ 158932-33-3 ]
  • [ 29388-59-8 ]
YieldReaction ConditionsOperation in experiment
51% With hydrogenchloride; water at 20 - 98℃; for 28h;
51% With hydrogenchloride In water at 98℃; for 4h; Synthesis of secoisolariciresinol Aqueous solution of SDG (8 ml, 0.15 mmol) was hydrolyzed with hydrochloric acid (4 ml, 6M) at 98 in water bath for 4 h. The received mixture was incubated for 24 h at room temperature. The secoisolariciresinol was crystallized and washed with ice water to give 0.027 g ((51%) yield) of off-white powder; mp 109.7-110.2 . IR (ν-cm-1): 3350, 2939, 2911, 2847, 1605, 1518, 1464, 1433, 1378, 1267, 1155, 1120, 1069, 1038, 879, 822, 801, 623, 564; MS (ESI) m/z: [M+H]+ 363.82. 1H NMR (400.13 MHz, DCl3) δ: 2.17 (2, m, H-2); 2.51 (2H, dd, J=13.7, 7.9 Hz, -1′); 2.57 (2H, dd, J=13.7, 6.4 Hz, H-1′b); 3.53 (2H, dd, J=8.6, 5.4 Hz, H-1); 3.80 (6H, s, OCH3); 3.92 (2H, dd, J=8.6, 6.5 Hz, H-1b); 5.73 (2H, broad s, Ar-OH); 6.49 (2H, d, J=1.8 Hz, H-2′′); 6.57 (2H, dd, J=7.9, 1.8 Hz, H-6′′); 6.79 (2H, d, J=7.9 Hz, H-5′′). 13C NMR (100.613 Hz, DCl3) δ: 39.1 (-1′); 46.4 (-2); 55.8 (OCH3); 73.2 (-1); 111.1 (-2′′); 114.2 (-5′′); 121.3 (-6′′); 132.6 (-1′′); 143.9 (-4′′); 146.5 (-3′′).
  • 3
  • [ 1456548-38-1 ]
  • [ 158932-33-3 ]
YieldReaction ConditionsOperation in experiment
81% With methanol; sodium methylate at 25℃; for 60h; Inert atmosphere; Secoisolariciresinol Diglucoside (R,R)-SDG-2 To a flask containing dry (R,R)-9 (0.041 g, 0.027 mmol, 1 equiv), a freshly prepared solution of NaOMe in MeOH (0.4 M, 2 mL, 28 equiv) was added and the solution stirred for 60 h at 25 °C. The solution was then filtered through a pad of silica (0.5 in, washing with MeOH) and the filtrate concentrated. The resulting solid was purified by preparative thin-layer chromatography (silica, 2 mm, 9:1 → 7:3 CH2Cl2:MeOH, then 5:5 CH2Cl2:MeOH half of plate length) and then passed through a small plug of reversed phase silica (100 Å C18, washing with MeOH) to provide (R,R)-SDG-2 (0.015 g, 0.022 mmol, 81% yield) as an off-white solid.
81% With sodium methylate In methanol at 25℃; for 60h; Inert atmosphere; 2; 9 Example 9: Synthesis of Secoisolariciresinol Diglucoside(/f,/f)-SDG-2 Example 9: Synthesis of Secoisolariciresinol Diglucoside(/f,/f)-SDG-2 To a flask containing dry (R,R)-9 (0.041 g, 0.027 mmol, 1 equiv), a freshly prepared solution of NaOMe in MeOH (0.4 M, 2 mL, 28 equiv) was added and the solution stirred for 60 h at 25 °C. The solution was then filtered through a pad of silica (0.5 in, washing with MeOH) and the filtrate concentrated. The resulting solid was purified by preparative thin- layer chromatography (silica, 2 mm, 9: 1→ 7:3 CH2Cl2:MeOH, then 5:5 CH2Cl2:MeOH half of plate length) and then passed through a small plug of reversed phase silica (100 A C18, washing with MeOH) to provide (R,R)-SOG-2 (0.015 g, 0.022 mmol, 81% yield) as an off- white solid. (R,R)-SDG-2: Rt = 0.50 (silica, 1 : 1 CH2Cl2:MeOH); [a]D32 = -22.2 (MeOH, c = 1.0); IR (film): vmax = 3336, 2949, 1651, 1409, 1014 cm"1; ]H NMR (600 MHz, CDC13) δ = 6.66 (d, / = 8.06 Hz, 2 H), 6.64 (d, / = 1.63 Hz, 2 H), 6.59 (dd, / = 8.06, 1.63 Hz, 2 H), 4.21 (d, / = 7.82 Hz, 2 H), 3.91 (dd, / = 10.11, 5.69 Hz, 2 H), 3.87 (dd, / = 12.01, 2.01 Hz, 2 H), 3.75 (s, 6 H), 3.67 (dd, / = 12.02, 5.47 Hz, 2 H), 3.58 (dd, / = 9.90, 5.36 Hz, 2 H), 3.38-3.18 (m, 8 H), 2.76-2.62 (m, 4 H), 2.14-2.07 (m, 2 H) ppm; 13C NMR (150 MHz, CDC13) δ = 148.77, 145.37, 134.05, 122.83, 115.70, 113.56, 104.59, 78.19, 77.93, 75.19, 71.70, 70.62, 62.79, 56.32, 41.63, 35.62 ppm; HRMS (ESI-TOF): calcd forC32H460i6 [M + H+]: 687.2858, found 687.2856.
  • 4
  • [ CAS Unavailable ]
  • [ 257930-74-8 ]
  • [ 158932-33-3 ]
YieldReaction ConditionsOperation in experiment
With methanol; sodium methylate at 5 - 20℃; for 40.5h; Inert atmosphere; Overall yield = ~ 100 g; 3 To a stirred solution of the 1 : 1 mixture of (S,S)-5 and (R,R)-6 from Example 2 (400.0 g, 0.26 mol) in MeOH (2500 mL) was added a solution of 30% NaOMe in MeOH (140 mL) at 5°C under N2 atmosphere through a dropping funnel for 30 min. After completion of the addition, the solution was stirred for 40 h at room temperature. The reaction was cooled and quenched with HC1 in isopropyl alcohol (IPA) to reach pH ~5 (~4 Molar HCI in IPA). After 10 minutes, volatiles were removed under reduced pressure. The residual was dissolved in MeOH (1000 mL) and cooled in the refrigerator overnight. The solid was removed by filtration. The solution was then absorbed onto silica gel and dried under vacuum. The obtained silica mixture was loaded onto a packed column. The product was purified by column chromatography (silica, 60-120 mesh) using 10-20% MeOH/dichloromethane. The product was checked by TLC and HPLC. Those fractions with >97% purity were combined and concentrated to give -100 g of a 1:1 mixture of (S.S)-SDG-l and (R.R)-SDG-2 as a white solid.
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