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[ CAS No. 13739-02-1 ] {[proInfo.proName]}

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Chemical Structure| 13739-02-1
Chemical Structure| 13739-02-1
Structure of 13739-02-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 13739-02-1 ]

CAS No. :13739-02-1 MDL No. :MFCD00468030
Formula : C19H12O8 Boiling Point : -
Linear Structure Formula :- InChI Key :TYNLGDBUJLVSMA-UHFFFAOYSA-N
M.W : 368.29 Pubchem ID :26248
Synonyms :
Diacerhein;Diacetylrhein;SF 277;4,5-Diacetylrhein;DAR

Calculated chemistry of [ 13739-02-1 ]

Physicochemical Properties

Num. heavy atoms : 27
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.11
Num. rotatable bonds : 5
Num. H-bond acceptors : 8.0
Num. H-bond donors : 1.0
Molar Refractivity : 89.71
TPSA : 124.04 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) : -7.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.0
Log Po/w (XLOGP3) : 1.9
Log Po/w (WLOGP) : 2.01
Log Po/w (MLOGP) : 1.14
Log Po/w (SILICOS-IT) : 2.91
Consensus Log Po/w : 1.99

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.32
Solubility : 0.177 mg/ml ; 0.000479 mol/l
Class : Soluble
Log S (Ali) : -4.13
Solubility : 0.0274 mg/ml ; 0.0000745 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.72
Solubility : 0.00707 mg/ml ; 0.0000192 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.08

Safety of [ 13739-02-1 ]

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

Application In Synthesis of [ 13739-02-1 ]

* 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 [ 13739-02-1 ]
  • Downstream synthetic route of [ 13739-02-1 ]

[ 13739-02-1 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 13739-02-1 ]
  • [ 478-43-3 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #2: With hydrogenchloride In water
Diacerein (150 g, 0.41 mol) was stirred in 10percent (w/w) Na2CO3 solution (4 L) resulting in a red mixture. After stirring overnight the mixture was acidified to pH2 with 5M HCI solution to give a yellow precipitate. This was filtered and dried in a vac-oven at 50 °C (168 g, >100percent). 'H NMR (400 MHz, DMSO): 7.40 (1H, d J=8 Hz), 7.71-7. 76 (2H, m), 7.82 (1 H, t J=8 Hz), 8.11 (1 H, d J=1. 6 Hz).
60% With sodium hydroxide In water for 0.5 h; Diacerein (0.012 M, 4.5 g) was dispersed in 80 ml of 10percent aqueous sodium hydroxide solution. The solution was heated on a boiling water bath for 30 min and then poured into 120 mL of 10percent HCl. Rhein was obtained in the form of yellow flakes which were recrystallized twice with pyridine. Rhein. mp 318–319 °C, Rf 0.58 (chloroform: methanol; 3:0.5 v/v),percent yield 60, Log P 0.2402. IR (ν, cm−1, KBr) 3566 (Phenolic OH stretch.), 3100, 2850 (Broad OH stretch. of COOH), 1682 (C=O stretch. of –COOH), 1193 (C–O stretch. of phenol), 1H NMR (δ, ppm, DMSO-d6) 8.57 carboxylic OH [s; 1H], 8.26 benzene CH2 [s; 2H], 8.25 benzene CH2 [s; 2H], 7.32–7.83 benzene CH2 [t; 3H], 3.79 phenolic OH [d; 2H].
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 7, p. 817 - 822
[2] Patent: WO2005/85170, 2005, A1, . Location in patent: Page/Page column 9-10
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7582 - 7587
[4] Journal of the Chemical Society, 1909, vol. 95, p. 1088
[5] Patent: US5480873, 1996, A,
[6] Patent: EP2196450, 2010, A1, . Location in patent: Page/Page column 6-7
  • 2
  • [ 13739-02-1 ]
  • [ 478-43-3 ]
  • [ 875535-36-7 ]
  • [ 875535-35-6 ]
Reference: [1] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2014, vol. 127, p. 355 - 360
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