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[ CAS No. 484-20-8 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 484-20-8
Chemical Structure| 484-20-8
Structure of 484-20-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 484-20-8 ]

CAS No. :484-20-8 MDL No. :MFCD00010272
Formula : C12H8O4 Boiling Point : -
Linear Structure Formula :- InChI Key :BGEBZHIAGXMEMV-UHFFFAOYSA-N
M.W : 216.19 Pubchem ID :2355
Synonyms :
5-Methoxypsoralen;5-MOP;NSC 95437;Heraclin

Calculated chemistry of [ 484-20-8 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 13
Fraction Csp3 : 0.08
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 58.75
TPSA : 52.58 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) : -6.25 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.29
Log Po/w (XLOGP3) : 1.93
Log Po/w (WLOGP) : 2.55
Log Po/w (MLOGP) : 1.18
Log Po/w (SILICOS-IT) : 2.88
Consensus Log Po/w : 2.16

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.93
Solubility : 0.253 mg/ml ; 0.00117 mol/l
Class : Soluble
Log S (Ali) : -2.66
Solubility : 0.475 mg/ml ; 0.0022 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.63
Solubility : 0.00501 mg/ml ; 0.0000232 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.9

Safety of [ 484-20-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335-H351-H361 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 484-20-8 ]

* 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 [ 484-20-8 ]
  • Downstream synthetic route of [ 484-20-8 ]

[ 484-20-8 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 122850-55-9 ]
  • [ 484-20-8 ]
Reference: [1] Heterocycles, 2005, vol. 65, # 8, p. 1985 - 1988
  • 2
  • [ 482-44-0 ]
  • [ 31575-93-6 ]
  • [ 484-20-8 ]
  • [ 1428263-43-7 ]
  • [ 1428263-44-8 ]
  • [ 1428263-45-9 ]
  • [ 1428263-47-1 ]
  • [ 1428417-34-8 ]
  • [ 1428263-46-0 ]
  • [ 1428417-33-7 ]
YieldReaction ConditionsOperation in experiment
1% With Penicillium janthinellum AS; liquid potato medium In acetone at 27℃; for 120 h; Microbiological reaction Screening scale biotransformation of IMP was carried out in 250-mL Erlenmeyer flasks containing 100 mL of liquid medium. The flasks were placed on a rotary shaker operating at 180 rpm and 27 °C. The substrates were dissolved in acetone to reach a final concentration of 10 mg/mL. After 36 h of pre-culture, 2 mg of IMP were added into each flask. The incubation was allowed to continue for 5 days. Culture controls consisted of fermentation blanks with microorganisms grown under identical non-substrate conditions. Substrate controls were composed of sterile medium with substrate, and they were incubated without microorganisms. (0009) Preparative scale biotransformation of IMP by P. janthinellum AS 3.510 was carried out in a 1-L Erlenmeyer flask. The substrate (10 mg) dissolved in acetone (0.5 mL) was added to pre-cultured medium (400 mL) and was incubated for an additional 5 days. In total, 800 mg of substrate were used for the preparative scale biotransformation. Other procedures were similar to the screening scale biotransformation.
Reference: [1] Food Chemistry, 2013, vol. 138, # 4, p. 2260 - 2266
  • 3
  • [ 108-73-6 ]
  • [ 484-20-8 ]
Reference: [1] Heterocycles, 2005, vol. 65, # 8, p. 1985 - 1988
[2] Heterocycles, 2005, vol. 65, # 8, p. 1985 - 1988
  • 4
  • [ 2174-64-3 ]
  • [ 484-20-8 ]
Reference: [1] Heterocycles, 2005, vol. 65, # 8, p. 1985 - 1988
[2] Heterocycles, 2005, vol. 65, # 8, p. 1985 - 1988
  • 5
  • [ 3067-10-5 ]
  • [ 484-20-8 ]
Reference: [1] Heterocycles, 2005, vol. 65, # 8, p. 1985 - 1988
[2] Heterocycles, 2005, vol. 65, # 8, p. 1985 - 1988
  • 6
  • [ 74794-29-9 ]
  • [ 484-20-8 ]
Reference: [1] Heterocycles, 2005, vol. 65, # 8, p. 1985 - 1988
[2] Heterocycles, 2005, vol. 65, # 8, p. 1985 - 1988
  • 7
  • [ 78045-69-9 ]
  • [ 484-20-8 ]
Reference: [1] Heterocycles, 2005, vol. 65, # 8, p. 1985 - 1988
[2] Heterocycles, 2005, vol. 65, # 8, p. 1985 - 1988
  • 8
  • [ 866081-74-5 ]
  • [ 484-20-8 ]
Reference: [1] Heterocycles, 2005, vol. 65, # 8, p. 1985 - 1988
  • 9
  • [ 866081-73-4 ]
  • [ 484-20-8 ]
Reference: [1] Heterocycles, 2005, vol. 65, # 8, p. 1985 - 1988
  • 10
  • [ 486-60-2 ]
  • [ 77-78-1 ]
  • [ 484-20-8 ]
Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 3488,3490
  • 11
  • [ 131623-13-7 ]
  • [ 484-20-8 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2498 - 2502
  • 12
  • [ 186581-53-3 ]
  • [ 486-60-2 ]
  • [ 484-20-8 ]
Reference: [1] Chemische Berichte, 1937, vol. 70, p. 478
[2] Journal of the Chemical Society, 1945, p. 540,542
[3] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2498 - 2502
  • 13
  • [ 484-20-8 ]
  • [ 486-60-2 ]
YieldReaction ConditionsOperation in experiment
82% With boron tribromide In dichloromethane at 0℃; for 2 h; General procedure: To an ice-cold solution (0 °C) of 8- or 5-MOP (1 mmol) or the corresponding bromides 12 or 26 (1 mmol) in CH2Cl2 (3.5 mL), a 1 M solution of BBr3 (4 mmol) in CH2Cl2 was added dropwise through a glass syringe. The resulting suspension was stirred at 0 °C for 1–2 h. After the completion of the reaction, ice-chips were added and the resulting mixture was extracted with CH2Cl2 and washed several times with H2O. The combined organic layers were dried with anhydrous Na2SO4 and evaporated to dryness to obtain the anticipated phenolic compounds.#10;#10;
80%
Stage #1: With boron tribromide In dichloromethane at 20℃; for 1 h; Inert atmosphere
Stage #2: With sodium hydrogencarbonate In dichloromethane; water
Bergaptol (13). To a solution of bergapten (14, 1.0 g, 4.63 mmol) in dichloromethane (20 ml) BBr3 (10 ml, 10 mmol, 1 100 mmol in DCM) was slowly added and the solution stirred under argon at room temperature. After 1 hours the mixture was poured slowly into a solution of saturated sodium bicarbonate (100 ml) resulting in the precipitation of a grey solid. The resulting colourless precipitate was recovered by filtration. The filtrate was neutralised with aq. HCl (1 M) to pH 7, to yield further product, which was also recovered by filtration. After 30 minutes the product was recovered by filtration, washed with cold water and ether and was dried under a high vacuum, yielding bergaptol (13) as an off-white solid (748 mg, 3.70 mmol, 80percent).
74%
Stage #1: With tetra-(n-butyl)ammonium iodide In dichloromethane at 0℃;
Stage #2: With boron trichloride In dichloromethane at 3.7 - 20℃; for 4.5 h;
To a heat-gun dried flask fitted with a graduated addition funnel under nitrogen was added


25.9 G (120 MMOL) OF BERGAPTEN 1, 59 G (160 MMOL ; 1.33 EQUIV. ) OF [BU4N] I AND 400 ML OF anhydrous CH, CL2. The resulting white slurry was immersed in an ice bath and the internal temperature monitored by a thermocouple. To the graduated addition funnel was added 400 mL of 1.0 M BC13 in CH, C12 ("smoking"during addition). THE BC13 SOLUTION was added dropwise to the slurry over the course of 2 hours (internal temperature up to 3. 7°C). After the addition was complete, the ice bath was removed and the reaction was allowed to warm to room temperature over the next 30 minutes. After stirring at room temperature for an additional 2 hours, the reaction mixture was quenched by pouring into 400 mL OF MEOH with vigorous stirring over 10 minutes (exothermic quench). The resulting pale yellow slurry was stirred for 15 minutes to cool to room temperature. Filtration through a coarse FRITTED-FUNNEL (-15 minutes) gave a pale yellow cake which was rinsed with 2 x 250 mL of acetone. After air-drying, 18.0 g (74percent yield) of bergaptol 2 was obtained as a pale yellow powder. This procedure is based on J. Org. Chem., 1999, 64 (26), 9719-21. 1H NMR (300 MHz, D6-DMSO) 8 11.3 (br, 1H), 8.25 (d, 1H, J=9.7), 7.90 (d, 1H, J=2.1), 7.19 (d, 1H, J=2.9), 7. 15 (s, 1H), 6. 25 (d, 1H, J=9.7). "C NMR (75. 4 MHZ, D6-DMSO) 8 160.4, 157. 0,152. 6,147. 9,144. 7, 139. 6,112. 5,110. 7, 104.8, 103.7, 90.8. When HPLC Method Two was used, the elution time was 6.4 minutes.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 20, p. 2593 - 2598
[2] Organic and Biomolecular Chemistry, 2006, vol. 4, # 8, p. 1604 - 1610
[3] European Journal of Medicinal Chemistry, 2013, vol. 60, p. 155 - 169
[4] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 2, p. 784 - 788
[5] Patent: WO2004/37827, 2004, A1, . Location in patent: Page 26
[6] Molecular Pharmacology, 2004, vol. 65, # 6, p. 1364 - 1374
[7] Molecular Pharmacology, 2005, vol. 68, # 5, p. 1254 - 1270
[8] Patent: US7772408, 2010, B1, . Location in patent: Page/Page column 5-6
  • 14
  • [ 484-20-8 ]
  • [ 737-52-0 ]
Reference: [1] Organic and Biomolecular Chemistry, 2006, vol. 4, # 8, p. 1604 - 1610
  • 15
  • [ 484-20-8 ]
  • [ 482-45-1 ]
Reference: [1] Organic and Biomolecular Chemistry, 2006, vol. 4, # 8, p. 1604 - 1610
  • 16
  • [ 484-20-8 ]
  • [ 870653-45-5 ]
Reference: [1] Molecular Pharmacology, 2005, vol. 68, # 5, p. 1254 - 1270
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