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[ CAS No. 1139-83-9 ] {[proInfo.proName]}

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Chemical Structure| 1139-83-9
Chemical Structure| 1139-83-9
Structure of 1139-83-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1139-83-9 ]

CAS No. :1139-83-9 MDL No. :MFCD00034338
Formula : C13H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :WXUQMTRHPNOXBV-UHFFFAOYSA-N
M.W : 212.20 Pubchem ID :5380406
Synonyms :
NSC 94726;3-hydroxy Urolithin

Calculated chemistry of [ 1139-83-9 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 14
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 62.01
TPSA : 50.44 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.69 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.81
Log Po/w (XLOGP3) : 2.68
Log Po/w (WLOGP) : 2.65
Log Po/w (MLOGP) : 2.26
Log Po/w (SILICOS-IT) : 2.98
Consensus Log Po/w : 2.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.49
Solubility : 0.0684 mg/ml ; 0.000322 mol/l
Class : Soluble
Log S (Ali) : -3.39
Solubility : 0.0862 mg/ml ; 0.000406 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.72
Solubility : 0.00406 mg/ml ; 0.0000191 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.75

Safety of [ 1139-83-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1139-83-9 ]

* 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 [ 1139-83-9 ]
  • Downstream synthetic route of [ 1139-83-9 ]

[ 1139-83-9 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 1143-62-0 ]
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YieldReaction ConditionsOperation in experiment
100% With boron tribromide In dichloromethane at 0℃; Inert atmosphere General procedure: A solution of methyl ether of urolithins A–C 30a–c (1.0equiv) was cooled at 0°C under Ar atmosphere and was added BBr3 slowly. Once the stating material was completely consumed by TLC, a solution of 2N HCl was added to acidify and partitioned with EtOAc to give the crude product. The crude product was purified by size exclusion chromatography to obtain the product.
89% With aluminum (III) chloride In o-xylene for 9 h; Reflux Anhydrous AlCl3 (2.1 g, 16 mmol) was added to a suspension of 3-methoxy-6H-benzo[c]chromen-6-one [ 15 ](0.90 g, 4.0 mmol) in o-xylene (20 mL) and the reaction mixture was refluxed for 9 h. After cooling to room temperature, the solvent was removed under rotary evaporation. The residue was diluted with CH2Cl2 (200 mL) and washed with 1 N aq. HCl (3 * 40 mL). The organic phase was washed with brine (100 mL) and dried over Na2SO4. The evaporation of the solvent under reduced pressure yielded a pink solid (0.76 g, 89percent) that was used without further purification. Spectroscopic data are in agreement with those reported in the literature [ 15 ].
Reference: [1] Tetrahedron, 2013, vol. 69, # 44, p. 9277 - 9283
[2] European Journal of Medicinal Chemistry, 2019, vol. 161, p. 433 - 444
[3] Journal of Organic Chemistry, 2017, vol. 82, # 10, p. 5080 - 5095
[4] ChemMedChem, 2010, vol. 5, # 9, p. 1616 - 1630
  • 2
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YieldReaction ConditionsOperation in experiment
66.3%
Stage #1: With sodium hydroxide In water for 0.5 h; Reflux
Stage #2: With copper(II) sulfate In water for 0.166667 h; Reflux
A solution of the 2-bromobenzoic acid (0.05 mol), resorcinol(0.1 mol), and sodium hydroxide (0.1 mol) in water (30 mL) washeated under reflux for 30 min. A 10percent aqueous solution of copper sulfate (5 mL) was then added where upon a slightly exothermic reaction ensued. The resulting mixture was heated under reflux for an additional 10 min and then cooled to 20 °C. The insoluble product was collected, washed well with water and dried. This material was of sufficient purity to be used as such for the preparations of the 3-hydroxy-6H-benzo[c]chromen-6-one, Yield: 66.3percent; mp: 230-231 °C (lit [31] 234-236 °C).
62%
Stage #1: With sodium hydroxide In water for 2 h; Reflux
Stage #2: With copper(ll) sulfate pentahydrate In water for 1 h; Reflux
Example 3Preparation of Urolithin B Urolithin B was prepared in one step by coupling resorcinol and 2-bromobenzoic acid following the procedure for the preparation of Urolithin A. The pure compound was obtained as a off-white powder with a yield of 61.6percent.
Reference: [1] European Journal of Organic Chemistry, 2013, # 25, p. 5631 - 5644
[2] European Journal of Medicinal Chemistry, 2014, vol. 74, p. 427 - 439
[3] Patent: WO2015/100213, 2015, A2, . Location in patent: Page/Page column 37
[4] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 9, p. 2239 - 2249
[5] Chemistry of Natural Compounds, 2002, vol. 38, # 5, p. 424 - 433
[6] RSC Advances, 2017, vol. 7, # 28, p. 17254 - 17263
[7] ChemMedChem, 2011, vol. 6, # 12, p. 2273 - 2286
[8] Angewandte Chemie - International Edition, 2017, vol. 56, # 39, p. 11841 - 11845[9] Angew. Chem., 2017, vol. 129, # 39, p. 12003 - 12007,5
[10] Journal of the Chemical Society, 1929, p. 1872
[11] Journal of the Indian Chemical Society, 1980, vol. 57, # 8, p. 837 - 840
[12] Patent: US2005/282781, 2005, A1, . Location in patent: Page/Page column 8
[13] Journal of Agricultural and Food Chemistry, 2009, vol. 57, # 21, p. 10181 - 10186
[14] Patent: WO2014/4902, 2014, A2, . Location in patent: Page/Page column 224-225
[15] Patent: WO2015/55736, 2015, A1, . Location in patent: Page/Page column 20
[16] Patent: US2008/31862, 2008, A1, . Location in patent: Page/Page column 6
  • 3
  • [ 88-67-5 ]
  • [ 108-46-3 ]
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YieldReaction ConditionsOperation in experiment
80.1%
Stage #1: With sodium hydroxide In water for 0.5 h; Reflux
Stage #2: With copper(II) sulfate In water for 0.166667 h; Reflux
Example 2: 3-hydroxy-6H-benzo[c]chromen-6-one A mixture of 2-lodobenzoic acid (30 gram, 0.12 mol), resorcinol (40 gram, 0.36 mol), and NaOH (17.4 g, 0.44 mol) in water (150 mL) is heated under reflux for 30 min. After the addition of aqueous CuS04 (28percent, 25 mL) the mixture is refluxed for additional 10 min, during which time the product (0.62 g) precipitates as a white powder. The precipitate is filtered and washed with cold water. Yield obtained: 80.1 percent, 1H NMR (DMSO) δ 6.71 (d, 1 H), 6.80 (dd, 1H), 7.51 (t, 1 H), 7.83 (t, 1 H), 8.08-8.22 (m, 3H ), 10.32 (s, 1 H).
80.1% With sodium hydroxide In water for 0.5 h; Reflux A mixture of 2-iodobenzoic acid (30 g, 0.12 mol), resorcinol(40 g, 0.36 mol), and NaOH (17.4 g, 0.44 mol) in water (150 mL)was heated under reflux for 30 min. After the addition of aqueousCuSO4 (28percent, 25 mL) the mixture was refluxed for additional10 min, during which time the product (0.62 g) precipitated as awhite powder. The precipitate was filtered and washed with coldwater. Yield obtained: 80.1percent, 1H NMR (DMSO-d6) d 6.71 (d, 1H),6.80 (dd, 1H, Ar-H), 7.51 (t, 1H, Ar-H), 7.83 (t, 1H, Ar-H), 8.08–8.22 (m, 3H, Ar-H), 10.32 (s, 1H, AOAH).
76%
Stage #1: With sodium hydroxide In water for 1 h; Reflux
Stage #2: With copper(II) sulfate In water for 0.166667 h; Reflux
A mixture of 2-iodobenzoic acid (6 mmol), resorcinol(18 mmol), and NaOH solution (22 mmol) in water (20 mL)was refluxed for 1 h. After the addition of aqueous CuSO4(15percent, 10 mL) to the mixture, refluxing was continued foradditional 10 min. The product was filtered, and washed withice-water and obtained as a white powder. 1H NMR (DMSOd6,400 MHz): δ = 10.30 (s, 1H, OH), 8.15–8.12 (m, 3H),7.86–7.83 (m, 1H), 7.50 (s, 1H), 6.77–6.74 (m, 2H). 13CNMR (DMSO-d6, 125 MHz) δ (ppm) major rotamer:160.5 ppm for lactone carbonyl. Yield obtained: 76percent.
72%
Stage #1: With sodium hydroxide In water for 1 h; Reflux
Stage #2: With copper(II) sulfate In water for 0.166667 h; Reflux
A mixture of 2-iodobenzoic acid (120 mmol), resorcinol(360 mmol), and NaOH solution (440 mmol) in water(50 mL) was refluxed for 1 h. After the addition of aqueousCuSO4 (28percent, 25 mL) to the mixture, refluxing was continuedfor 10 min. The product was filtered, and washed withice-water and obtained as a white powder. Yield obtained:72percent. 1H NMR (DMSO-d6, 400 MHz): δ = 10.30 (s, 1H,OH), 8.17 (m, 3H, Ar-H), 7.87 (t, 1H, Ar-H), 7.50 (t, 1H, Ar-H), 6.76 (m, 2H, Ar-H).

Reference: [1] Patent: WO2014/129989, 2014, A1, . Location in patent: Page/Page column 13
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 19, p. 5141 - 5154
[3] Journal of Fluorescence, 2018, vol. 28, # 5, p. 1255 - 1259
[4] Letters in Drug Design and Discovery, 2018, vol. 15, # 11, p. 1131 - 1140
  • 4
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Reference: [1] Patent: US2005/282781, 2005, A1, . Location in patent: Page/Page column 10
[2] Patent: US2005/282781, 2005, A1, . Location in patent: Page/Page column 10
  • 5
  • [ 3722-44-9 ]
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Reference: [1] Journal of the Chemical Society, 1940, p. 1393,1395
[2] Journal of the Chemical Society, 1940, p. 1393,1395
[3] ChemMedChem, 2010, vol. 5, # 9, p. 1616 - 1630
  • 6
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Reference: [1] Patent: US2005/282781, 2005, A1, . Location in patent: Page/Page column 10
  • 7
  • [ 54245-26-0 ]
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Reference: [1] ChemMedChem, 2010, vol. 5, # 9, p. 1616 - 1630
  • 8
  • [ 1655-07-8 ]
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Reference: [1] ChemMedChem, 2010, vol. 5, # 9, p. 1616 - 1630
  • 9
  • [ 108-46-3 ]
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Reference: [1] ChemMedChem, 2010, vol. 5, # 9, p. 1616 - 1630
  • 10
  • [ 1459238-41-5 ]
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Reference: [1] Tetrahedron, 2013, vol. 69, # 44, p. 9277 - 9283
  • 11
  • [ 56031-19-7 ]
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Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 10, p. 5080 - 5095
  • 12
  • [ 18110-71-9 ]
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Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 10, p. 5080 - 5095
  • 13
  • [ 696-62-8 ]
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Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 10, p. 5080 - 5095
  • 14
  • [ 98-88-4 ]
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Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 10, p. 5080 - 5095
  • 15
  • [ 77645-50-2 ]
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Reference: [1] Tetrahedron, 1992, vol. 48, # 38, p. 8179 - 8188
  • 16
  • [ 10417-94-4 ]
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Reference: [1] Patent: US2005/282781, 2005, A1, . Location in patent: Page/Page column 10
[2] Patent: US2005/282781, 2005, A1, . Location in patent: Page/Page column 10
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Reference: [1] Patent: US2005/282781, 2005, A1, . Location in patent: Page/Page column 10
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