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Chemical Structure| 331-39-5
Chemical Structure| 331-39-5
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Product Details of [ 331-39-5 ]

CAS No. :331-39-5 MDL No. :MFCD00004392
Formula : C9H8O4 Boiling Point : -
Linear Structure Formula :- InChI Key :QAIPRVGONGVQAS-DUXPYHPUSA-N
M.W : 180.16 Pubchem ID :689043
Synonyms :
3,4-Dihydroxycinnamic Acid
Chemical Name :3-(3,4-Dihydroxyphenyl)acrylic acid

Calculated chemistry of [ 331-39-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 47.16
TPSA : 77.76 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) : -6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.97
Log Po/w (XLOGP3) : 1.15
Log Po/w (WLOGP) : 1.09
Log Po/w (MLOGP) : 0.7
Log Po/w (SILICOS-IT) : 0.75
Consensus Log Po/w : 0.93

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.89
Solubility : 2.32 mg/ml ; 0.0129 mol/l
Class : Very soluble
Log S (Ali) : -2.38
Solubility : 0.755 mg/ml ; 0.00419 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.71
Solubility : 35.1 mg/ml ; 0.195 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.81

Safety of [ 331-39-5 ]

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 [ 331-39-5 ]

* 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 [ 331-39-5 ]
  • Downstream synthetic route of [ 331-39-5 ]

[ 331-39-5 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 331-39-5 ]
  • [ 2316-26-9 ]
Reference: [1] Journal of Enzyme Inhibition and Medicinal Chemistry, 2011, vol. 26, # 4, p. 485 - 497
  • 2
  • [ 215872-63-2 ]
  • [ 1135-24-6 ]
  • [ 621-54-5 ]
  • [ 1135-23-5 ]
  • [ 331-39-5 ]
  • [ 102-32-9 ]
  • [ 306-08-1 ]
  • [ 1078-61-1 ]
  • [ 1081-71-6 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2009, vol. 57, # 8, p. 3356 - 3362
  • 3
  • [ 215872-63-2 ]
  • [ 1135-24-6 ]
  • [ 621-54-5 ]
  • [ 1135-23-5 ]
  • [ 331-39-5 ]
  • [ 102-32-9 ]
  • [ 306-08-1 ]
  • [ 1078-61-1 ]
  • [ 23028-17-3 ]
  • [ 2475-56-1 ]
  • [ 1081-71-6 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2009, vol. 57, # 8, p. 3356 - 3362
  • 4
  • [ 331-39-5 ]
  • [ 74-88-4 ]
  • [ 537-73-5 ]
Reference: [1] Yakugaku Zasshi, 1939, vol. 59, p. engl. Ref. S. 261, 264[2] Chem.Abstr., 1940, p. 1006
  • 5
  • [ 331-39-5 ]
  • [ 6537-80-0 ]
Reference: [1] Helvetica Chimica Acta, 2002, vol. 85, # 8, p. 2328 - 2334
  • 6
  • [ 331-39-5 ]
  • [ 73635-75-3 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 19, p. 3303 - 3305
  • 7
  • [ 60-12-8 ]
  • [ 331-39-5 ]
  • [ 104594-70-9 ]
YieldReaction ConditionsOperation in experiment
48% With ytterbium(III) triflate In nitromethane at 120℃; for 0.666667 h; To a mixture of caffeic acid fine powder (1.0 g, 5.56 mmol, 1.0 equiv.),alcohol (5.56 mmol, 1.0 equiv.) in nitromethane (125 mL) was addedytterbium triflate (34.4 mg, 0.056 mmol, 0.01 equiv.). After 5 min inan ultrasonic bath the mixture without protective gas was stirred ona 120 °C oil bath for a given time. The reaction mixture was cooled toroom temperature, washed with deionised water (30 mL), 2percent NaHCO3(30 mL) and brine, dried over anhydrous Na2SO4 and evaporated underreduced pressure to give the crude product, which was purified on asilica gel column to give the compounds 1–5 and 8–30.2-Phenethyl (E)-3-(3,4-dihydroxyphenyl) acrylate (1): Whitesolid; yield 758 mg, 48.0percent; m.p. 128–130 °C (lit.20 116–123 °C);IR (KBr) νmax 3480, 3328, 1683, 1601, 1362, 1301, 1279, 1182 cm–1;1H NMR (400 MHz, DMSO-d6) δH 7.46 (1H, d, J = 16 Hz, CH=CHCO),7.34–7.18 (5H, m, C6H5), 7.05 (1H, s, 2‑ArH), 6.99 (1H, d, J = 8.0 Hz,6‑ArH), 6.77 (1H, d, J = 8.0 Hz, 5‑ArH), 6.24 (1H, d, J = 16 Hz,CH=CHCO), 4.32 (2H, t, J = 6.8 Hz, OCH2), 2.94 (2H, t, J = 6.8 Hz,OCH2CH2) ppm; 13C NMR (100 MHz, DMSO-d6) δC 166.4, 148.3,145.4, 145.1, 138.0, 128.8, 128.3, 126.3, 125.4, 121.4, 115.7, 114.7, 113.8,64.3, 34.4 ppm; HRMS-ESI C17H16O4 calcd [M–H]– 283.0970, found283.0966.
48% With ytterbium(III) triflate In nitromethane at 120℃; General procedure: To a mixture of caffeic acid fine powder (1.0 g, 5.56 mmol), various phenethyl alcohols (5.56 mmol) in CH3NO2 (125 mL) was added Yb(OTf)3 (34.4 mg, 0.056 mmol). After 5 min of ultrasonic shake, the mixture was stirred on a 120 °C oil bath for 40-120 min. The reaction mixture was cooled to room temperature, washed with 2percent NaHCO3 (30 mL) and brine, dried over anhydrous Na2SO4, and concentrated to give crude products, which were purified by column chromatography to give the compounds 1-26 in 18-61percent yields. Phenethyl (E)-3-(3,4-dihydroxyphenyl) acrylate (CAPE). White solid (48percent yield for esterification reaction); Mp 128–130 °C; 1H NMR (400 MHz, DMSO-d6) δH 7.46 (1H, d, J = 16.0 Hz, CH=CHCO), 7.34-7.18 (5H, m, C6H5), 7.05 (1H, s, 2-ArH), 6.99 (1H, d, J = 8.0 Hz, 5-ArH), 6.77 (1H, d, J = 8.0 Hz, 6-ArH), 6.24 (1H, d, J = 16.0 Hz, CH=CHCO), 4.32 (2H, t, J = 6.8 Hz, OCH2), 2.94 (2H, t, J = 6.8 Hz, CH2C6H5) ppm; 13C NMR (100 MHz, DMSO-d6) δC 166.4, 148.3, 145.4, 145.1, 138.0, 128.8, 128.3, 126.3, 125.4, 121.4, 115.7, 114.7, 113.8, 64.3, 34.4 ppm; HRMS-ESI C17H16O4 calcd [M-H]- 283.0970, found 283.0966.
Reference: [1] Patent: EP1211237, 2002, A1, . Location in patent: Example 1
[2] Organic Letters, 2002, vol. 4, # 22, p. 3839 - 3841
[3] Journal of Chemical Research, 2014, vol. 38, # 11, p. 695 - 700
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 131 - 134
[5] Patent: EP1211237, 2002, A1, . Location in patent: Page 5
[6] Patent: EP1211237, 2002, A1, . Location in patent: Page 5
[7] Journal of Medicinal Chemistry, 1995, vol. 38, # 21, p. 4171 - 4178
[8] Patent: US5610185, 1997, A,
[9] Chemical and Pharmaceutical Bulletin, 2017, vol. 65, # 11, p. 1020 - 1027
  • 8
  • [ 331-39-5 ]
  • [ 103-63-9 ]
  • [ 104594-70-9 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 2, p. 236 - 238
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 16, p. 7584 - 7597
[3] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 1, p. 199 - 209
  • 9
  • [ 331-39-5 ]
  • [ 104594-70-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 10, p. 3351 - 3359
[2] European Journal of Medicinal Chemistry, 2014, vol. 75, p. 391 - 402
  • 10
  • [ 60-12-8 ]
  • [ 331-39-5 ]
  • [ 104594-70-9 ]
Reference: [1] Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 2, p. 124 - 131[2] Bioorganicheskaya Khimiya, 1995, vol. 21, # 2, p. 143 - 151
  • 11
  • [ 331-39-5 ]
  • [ 538-75-0 ]
  • [ 104594-70-9 ]
Reference: [1] Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 2, p. 124 - 131[2] Bioorganicheskaya Khimiya, 1995, vol. 21, # 2, p. 143 - 151
  • 12
  • [ 1049703-62-9 ]
  • [ 331-39-5 ]
  • [ 77-95-2 ]
  • [ 2450-53-5 ]
Reference: [1] Agricultural and Biological Chemistry, 1985, vol. 49, # 8, p. 2467 - 2470
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