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Chemical Structure| 121-34-6
Chemical Structure| 121-34-6
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Product Details of [ 121-34-6 ]

CAS No. :121-34-6 MDL No. :MFCD00002551
Formula : C8H8O4 Boiling Point : -
Linear Structure Formula :- InChI Key :WKOLLVMJNQIZCI-UHFFFAOYSA-N
M.W : 168.15 Pubchem ID :8468
Synonyms :
4-hydroxy-3-methoxybenzoic acid
Chemical Name :4-Hydroxy-3-methoxybenzoic acid

Calculated chemistry of [ 121-34-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.92
TPSA : 66.76 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) : -6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.4
Log Po/w (XLOGP3) : 1.43
Log Po/w (WLOGP) : 1.1
Log Po/w (MLOGP) : 0.74
Log Po/w (SILICOS-IT) : 0.73
Consensus Log Po/w : 1.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.02
Solubility : 1.6 mg/ml ; 0.00952 mol/l
Class : Soluble
Log S (Ali) : -2.44
Solubility : 0.615 mg/ml ; 0.00366 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.32
Solubility : 8.1 mg/ml ; 0.0482 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.42

Safety of [ 121-34-6 ]

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 [ 121-34-6 ]

* 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 [ 121-34-6 ]
  • Downstream synthetic route of [ 121-34-6 ]

[ 121-34-6 ] Synthesis Path-Upstream   1~29

  • 1
  • [ 75598-56-0 ]
  • [ 121-34-6 ]
  • [ 2415-24-9 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 5, p. 1023 - 1025
  • 2
  • [ 121-34-6 ]
  • [ 499-80-9 ]
Reference: [1] Green Chemistry, 2015, vol. 17, # 11, p. 4974 - 4979
[2] Patent: US2018/148752, 2018, A1, . Location in patent: Paragraph 0182-0183; 0184-0185; 0197
  • 3
  • [ 121-34-6 ]
  • [ 100-26-5 ]
Reference: [1] Green Chemistry, 2015, vol. 17, # 11, p. 4974 - 4979
[2] Patent: US2018/148752, 2018, A1, . Location in patent: Paragraph 0182-0183; 0186-0187; 0197
  • 4
  • [ 121-34-6 ]
  • [ 137-07-5 ]
  • [ 36341-25-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 5, p. 984 - 1000
  • 5
  • [ 121-34-6 ]
  • [ 619-05-6 ]
Reference: [1] Patent: WO2012/75053, 2012, A2, . Location in patent: Page/Page column 84
  • 6
  • [ 121-34-6 ]
  • [ 60547-92-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 15, p. 1933 - 1935
[2] Synthesis, 1990, # 1, p. 81 - 84
[3] Patent: WO2015/28850, 2015, A1,
[4] Patent: WO2015/155753, 2015, A2,
[5] Patent: WO2016/59622, 2016, A2,
[6] Patent: WO2018/86139, 2018, A1,
  • 7
  • [ 121-34-6 ]
  • [ 3943-74-6 ]
  • [ 6702-50-7 ]
Reference: [1] Patent: US6384080, 2002, B1,
  • 8
  • [ 64-17-5 ]
  • [ 121-34-6 ]
  • [ 617-05-0 ]
YieldReaction ConditionsOperation in experiment
98% for 48 h; Inert atmosphere; Reflux Synthesis of ethyl 4-hydroxy-3-methoxybenzoate: In a round bottomed flask equipped with a nitrogen inlet and a magnetic stir bar, a solution of vanillic acid (10 g, 59.49 mmol) in EtOH (400 mL) was added. To the above solution 600 mg (6.11 mmol) of cone. H2SO4 was added. The mixture was then stirred at reflux temperature for 48 h. The solution was rotary evaporated. Water (100 mL) was then added to the residue and the separated greenish oil was then removed by using separately funnel. Product was then dried in vacuo to obtain 11.45 g (98 percent) of ethyl 4-hydroxy-3-methoxybenzoate. 1H NMR (400 MHz, Chloroform-d) δ 7.62 (dd, J= 8.5, 2.1 Hz, 1H), 7.53 (d, J= 1.8 Hz, 1H), 6.91 (d, J= 8.6 Hz, 1H), 4.33 (q, J= 7.1 Hz, 2H), 3.91 (s, 3H), 1.36 (t, J= 7.3 Hz, 3H). HPLC-MS: Expected: 197 (MH+); Found: 197.
98% for 48 h; Reflux; Inert atmosphere In a round bottomed flask equipped with a nitrogen inlet and a magnetic stir bar, a solution of 4-hydroxy-3- methoxybenzoic acid (10 g, 59.49 mmol) in EtOH (400 mL) was added. To the above solution 600 mg (6.11 mmol) of cone. H2SO4 was added. The mixture was then stirred at reflux temperature for 48 h. The solution was rotary evaporated. Water (100 mL) was then added to the residue and a greenish oily compound separates out. The greenish oil was then separated and then dried in vacuo to 11.45 g (98 percent) of ethyl 4-hydroxy-3- methoxybenzoate. (0284) 1H NMR (400 MHz, Chloroform-d) δ 7.62 (dd, J = 8.5, 2.1 Hz, 1H), 7.53 (d, J = 1.8 Hz, 1H), 6.91 (d, J = 8.6 Hz, 1H), 4.33 (q, J = 7.1 Hz, 2H), 3.91 (s, 3H), 1.36 (t, J = 7.3 Hz, 3H). HPLC-MS: Expected: 197 (MH+); Found: 197
Reference: [1] Patent: WO2017/62804, 2017, A1, . Location in patent: Paragraph 0070
[2] Patent: WO2018/144900, 2018, A1, . Location in patent: Page/Page column 47-48
[3] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 13, p. 4279 - 4290
[4] Chemische Berichte, 1877, vol. 10, p. 60 Anm.
[5] Molecular crystals and liquid crystals, 1982, vol. 99, # 1-4, p. 279 - 284
[6] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 4, p. 526 - 531
[7] Journal of Heterocyclic Chemistry, 2010, vol. 47, # 4, p. 838 - 845
[8] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 14, p. 4226 - 4236
[9] MedChemComm, 2013, vol. 4, # 5, p. 827 - 832
[10] Patent: WO2014/31784, 2014, A1, . Location in patent: Paragraph 0573
[11] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 6014 - 6024
[12] New Journal of Chemistry, 2016, vol. 40, # 8, p. 6977 - 6985
  • 9
  • [ 121-34-6 ]
  • [ 617-05-0 ]
YieldReaction ConditionsOperation in experiment
80% With sulfuric acid; sodium hydrogencarbonate; mercury In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate EXAMPLE 2
Preparation of ethyl 4-hydroxy-3-methoxybenzoate (ethyl vanillate)
50 g of vanillic acid and 250 ml of methanol were introduced into a reactor.
40 ml of sulfuric acid was introduced dropwise using a dropping funnel; cooling was carried out if the alcohol boiled.
The mixture was refluxed for 2 hours with stirring.
The mixture was cooled to room temperature, poured into 100 ml of ice water, and the alcohol was evaporated off under reduced pressure.
The aqueous phase was extracted three times with ethyl ether.
The combined organic phases were washed with a saturated solution of sodium bicarbonate until the pH was neutral, then washed once with water to eliminate the salts.
The organic phase was dried over magnesium sulfate and evaporated under reduced pressure (200 mm of mercury=2.6600 Pa) to obtain the crude ester.
The ethyl ester was distilled at 132° C. under a reduced pressure of 2 mm of mercury (266 PA), then crystallized from petroleum ether (40°-60° C. fraction) to provide ethyl vanillate having a purity of more than 97percent at a yield of 80percent.
The ethyl vanillate has a spicy vanilla scent.
Reference: [1] Patent: US5686406, 1997, A,
  • 10
  • [ 121-34-6 ]
  • [ 617-05-0 ]
Reference: [1] Patent: US2004/106601, 2004, A1,
[2] Patent: US2004/224943, 2004, A1,
[3] Patent: US2004/229866, 2004, A1,
[4] Patent: US2004/254173, 2004, A1,
[5] Patent: US2004/138210, 2004, A1,
[6] Patent: US2004/138209, 2004, A1,
[7] Patent: US2004/106602, 2004, A1,
[8] Patent: US6638928, 2003, B1,
  • 11
  • [ 121-34-6 ]
  • [ 75-03-6 ]
  • [ 617-05-0 ]
Reference: [1] Synthetic Communications, 1998, vol. 28, # 11, p. 2021 - 2026
  • 12
  • [ 121-34-6 ]
  • [ 78-39-7 ]
  • [ 617-05-0 ]
Reference: [1] Synthetic Communications, 2002, vol. 32, # 14, p. 2209 - 2213
  • 13
  • [ 121-34-6 ]
  • [ 4998-07-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 13, p. 3529 - 3542
  • 14
  • [ 586-38-9 ]
  • [ 121-34-6 ]
  • [ 877-22-5 ]
  • [ 99-06-9 ]
Reference: [1] Canadian Journal of Chemistry, 2001, vol. 79, # 4, p. 394 - 404
  • 15
  • [ 586-38-9 ]
  • [ 99-50-3 ]
  • [ 121-34-6 ]
  • [ 877-22-5 ]
  • [ 99-06-9 ]
Reference: [1] Canadian Journal of Chemistry, 2001, vol. 79, # 4, p. 394 - 404
  • 16
  • [ 586-38-9 ]
  • [ 121-34-6 ]
  • [ 877-22-5 ]
  • [ 2612-02-4 ]
  • [ 99-06-9 ]
Reference: [1] Canadian Journal of Chemistry, 2001, vol. 79, # 4, p. 394 - 404
  • 17
  • [ 586-38-9 ]
  • [ 121-34-6 ]
  • [ 877-22-5 ]
  • [ 2612-02-4 ]
  • [ 99-06-9 ]
Reference: [1] Canadian Journal of Chemistry, 2001, vol. 79, # 4, p. 394 - 404
  • 18
  • [ 121-34-6 ]
  • [ 61032-41-5 ]
Reference: [1] Asian Journal of Chemistry, 2015, vol. 27, # 7, p. 2647 - 2650
  • 19
  • [ 121-34-6 ]
  • [ 28165-49-3 ]
Reference: [1] Journal of the Chemical Society, 1908, vol. 93, p. 789
  • 20
  • [ 121-34-6 ]
  • [ 3535-33-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 16, p. 4971 - 4984
  • 21
  • [ 121-34-6 ]
  • [ 2486-69-3 ]
Reference: [1] Patent: US2012/107886, 2012, A1, . Location in patent: Page/Page column 19
[2] Patent: WO2012/75053, 2012, A2, . Location in patent: Page/Page column 83-84
  • 22
  • [ 121-34-6 ]
  • [ 15785-54-3 ]
YieldReaction ConditionsOperation in experiment
44% With nitric acid In acetic acid at 20℃; for 0.5 h; To a solution of vanillic acid (20 g, 119 mmol) in acetic acid (200 mL) was added 60percent nitric acid (9.7 mL, 126.4 mmol) dropwise. The reaction mixture was stirred at room temperature for 0.5 h, and then poured into ice-water. The resulting precipitate was filtered off, washed with water, and dried under vacuum to give the product as a yellow powder. The yield was 11.28 g (44percent), mp: 216-219°C (216°C)2.
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3396 - 3411
[2] Chemistry Letters, 2016, vol. 45, # 4, p. 439 - 441
[3] Patent: EP1845097, 2007, A1, . Location in patent: Page/Page column 7
[4] Patent: WO2013/89573, 2013, A1, . Location in patent: Page/Page column 17-18
  • 23
  • [ 121-34-6 ]
  • [ 4097-63-6 ]
  • [ 15785-54-3 ]
Reference: [1] Monatshefte fuer Chemie, 1914, vol. 35, p. 95
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 1100
  • 24
  • [ 121-34-6 ]
  • [ 3251-56-7 ]
  • [ 15785-54-3 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, # 10, p. 1845 - 1850[2] Zhurnal Organicheskoi Khimii, 1983, vol. 19, # 10, p. 2124 - 2130
  • 25
  • [ 56-23-5 ]
  • [ 7732-18-5 ]
  • [ 121-33-5 ]
  • [ 121-34-6 ]
  • [ 15785-54-3 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 1100
  • 26
  • [ 121-34-6 ]
  • [ 7697-37-2 ]
  • [ 4097-63-6 ]
  • [ 15785-54-3 ]
Reference: [1] Monatshefte fuer Chemie, 1914, vol. 35, p. 95
  • 27
  • [ 121-34-6 ]
  • [ 7782-77-6 ]
  • [ 3251-56-7 ]
  • [ 15785-54-3 ]
Reference: [1] Comment. phys. math., 1956, vol. 19, # 1, p. 40
  • 28
  • [ 121-34-6 ]
  • [ 56441-97-5 ]
Reference: [1] Asian Journal of Chemistry, 2015, vol. 27, # 7, p. 2647 - 2650
  • 29
  • [ 121-34-6 ]
  • [ 162364-72-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 23, p. 4910 - 4925
[2] Journal of Medicinal Chemistry, 2002, vol. 45, # 17, p. 3772 - 3793
[3] ChemMedChem, 2014, vol. 9, # 7, p. 1476 - 1487
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