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[ CAS No. 494-08-6 ] {[proInfo.proName]}

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Chemical Structure| 494-08-6
Chemical Structure| 494-08-6
Structure of 494-08-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 494-08-6 ]

CAS No. :494-08-6 MDL No. :MFCD00210591
Formula : C14H18O8 Boiling Point : -
Linear Structure Formula :- InChI Key :LPRNQMUKVDHCFX-RKQHYHRCSA-N
M.W : 314.29 Pubchem ID :6452133
Synonyms :
Vanillin 4-O-β-D-Glucoside

Calculated chemistry of [ 494-08-6 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 5
Num. H-bond acceptors : 8.0
Num. H-bond donors : 4.0
Molar Refractivity : 72.47
TPSA : 125.68 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -9.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : -1.58
Log Po/w (WLOGP) : -1.31
Log Po/w (MLOGP) : -1.83
Log Po/w (SILICOS-IT) : -0.49
Consensus Log Po/w : -0.69

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.67
Solubility : 68.0 mg/ml ; 0.216 mol/l
Class : Very soluble
Log S (Ali) : -0.55
Solubility : 88.4 mg/ml ; 0.281 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.28
Solubility : 166.0 mg/ml ; 0.527 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 4.2

Safety of [ 494-08-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 494-08-6 ]

* 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 [ 494-08-6 ]
  • Downstream synthetic route of [ 494-08-6 ]

[ 494-08-6 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 51482-43-0 ]
  • [ 494-08-6 ]
YieldReaction ConditionsOperation in experiment
94% With potassium carbonate In tetrahydrofuran; methanol; water at 40℃; for 0.333333 h; Vanillin 2, 3, 4, 6-tetra-O-acetyl-b-D-glucopyranoside 3 (1.36 g,3.0 mmol) was dissolved in THF/CH3OH/H2O (33 mL, v:v:v 5:5:1),and then K2CO3 (0.83 g, 6.0 mmol)was added. After stirring at 40 Cfor 20 min, the reaction was quenched with 1M HCl and thenconcentrated. The residue was purified by silica gel column chromatography(CH2Cl2/CH3OH, 15:1) to afford 4 as a white solid(0.88 g, 94percent). [a]D20 -11.4 (c 1.0, H2O). 1H NMR (DMSO-d6, 400 MHz) d: 9.86 (s, 1H, CHO), 7.52 (dd, J 8.3, 1.5 Hz, 1H, Ph-H), 7.43 (d,J 1.4 Hz, 1H, Ph-H), 7.28 (d, J 8.4 Hz,1H, Ph-H), 5.39 (d, J 4.4 Hz,1H, -OH), 5.16 (d, J 3.7 Hz, 1H, -OH), 5.09 (d, J 5.2 Hz, 2H, -OH, H-1), 4.59 (t, J 5.6 Hz, 1H, -OH), 3.84 (s, 3H, -OMe), 3.66 (dd, J 11.2,4.7 Hz, 1H, H-3), 3.48e3.45 (m, 1H, H-2), 3.40e3.37 (m, 1H, H-4),3.30e3.25 (m, 2H, H-6), 3.20e3.14 (m, 1H, H-5); 13C NMR (DMSOd6,150 MHz)) d: 191.66 (CHO), 151.78,149.34, 130.56,125.43,114.58,110.52, 99.41 (C-1), 77.17, 76.84, 73.11, 69.58, 60.62, 55.70; ESIHRMSm/z [MNa] calculated for C14H18NaO8 337.0894 found337.0901.
75 mg With sodium methylate In methanol at 20℃; for 1 h; Inert atmosphere General procedure: To a solution 2 and the acceptor ArOH (3.0 equiv) in dry DCM (0.1 M) was added afreshly prepared solution of BF3•OEt2 (1.0 equiv., 1M in dry DCM). The solution wasstirred 1 h and followed by TLC (30:70; EtOAc : hexanes). A solution of NaHCO3(aq) wasadded and the mixture was extracted with DCM, washed with brine, dried over Na2SO4,filtered and concentrated in vacuo. The α/β ratio was measured by 1H NMR on the crude.The residue was treated with a freshly prepared solution MeONa (0.25 equiv., 0.5 M inmethanol) in dry methanol (0.3 M). The solution was stirred at r.t. for 1 h andneutralized with Amberlite IR-120 H+, filtered and concentrated in vacuo to give a whitesolid. Quick flash column chromatography (10:90; MeOH:DCM) removed excess of ArOHand led to the β-D anomer, which was recrystallized in hot ethanol.
Reference: [1] Carbohydrate Research, 2018, vol. 460, p. 41 - 46
[2] Journal of Agricultural and Food Chemistry, 2009, vol. 57, # 5, p. 2056 - 2064
[3] Synthesis (Germany), 2016, vol. 48, # 20, p. 3575 - 3588
  • 2
  • [ 121-33-5 ]
  • [ 494-08-6 ]
Reference: [1] Molecules, 2012, vol. 17, # 5, p. 5013 - 5020
  • 3
  • [ 604-69-3 ]
  • [ 494-08-6 ]
Reference: [1] Synthesis (Germany), 2016, vol. 48, # 20, p. 3575 - 3588
[2] Carbohydrate Research, 2018, vol. 460, p. 41 - 46
  • 4
  • [ 121-33-5 ]
  • [ 494-08-6 ]
Reference: [1] Carbohydrate Research, 2018, vol. 460, p. 41 - 46
[2] Carbohydrate Research, 2018, vol. 460, p. 41 - 46
[3] Carbohydrate Research, 2018, vol. 460, p. 41 - 46
  • 5
  • [ 572-09-8 ]
  • [ 494-08-6 ]
Reference: [1] Synthesis (Germany), 2016, vol. 48, # 20, p. 3575 - 3588
  • 6
  • [ 4336-91-8 ]
  • [ 494-08-6 ]
Reference: [1] Synthesis (Germany), 2016, vol. 48, # 20, p. 3575 - 3588
  • 7
  • [ 74808-10-9 ]
  • [ 494-08-6 ]
Reference: [1] Carbohydrate Research, 2018, vol. 460, p. 41 - 46
  • 8
  • [ 572-09-8 ]
  • [ 494-08-6 ]
Reference: [1] Carbohydrate Research, 2018, vol. 460, p. 41 - 46
  • 9
  • [ 2280-44-6 ]
  • [ 121-33-5 ]
  • [ 494-08-6 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 5, p. 695 - 699
  • 10
  • [ 2280-44-6 ]
  • [ 121-33-5 ]
  • [ 494-08-6 ]
Reference: [1] European Journal of Medicinal Chemistry, 2006, vol. 41, # 9, p. 1059 - 1072
  • 11
  • [ 133-89-1 ]
  • [ 121-33-5 ]
  • [ 494-08-6 ]
Reference: [1] Phytochemistry, 2009, vol. 70, # 4, p. 473 - 482
  • 12
  • [ 121-33-5 ]
  • [ 57-50-1 ]
  • [ 494-08-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 4, p. 361 - 365
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