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[ CAS No. 93-14-1 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 93-14-1
Chemical Structure| 93-14-1
Structure of 93-14-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 93-14-1 ]

CAS No. :93-14-1 MDL No. :MFCD00016873
Formula : C10H14O4 Boiling Point : -
Linear Structure Formula :- InChI Key :HSRJKNPTNIJEKV-UHFFFAOYSA-N
M.W : 198.22 Pubchem ID :3516
Synonyms :
Guaiacol glyceryl ether;Guaiphenesin;Scott Tussin;Methphenoxydiol;XL90;SL 90;NSC 62112;MY-301;Glycerol guaiacolate

Calculated chemistry of [ 93-14-1 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 51.36
TPSA : 58.92 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) : -6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.6
Log Po/w (XLOGP3) : 1.39
Log Po/w (WLOGP) : 0.43
Log Po/w (MLOGP) : 0.37
Log Po/w (SILICOS-IT) : 1.14
Consensus Log Po/w : 0.98

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.93
Solubility : 2.32 mg/ml ; 0.0117 mol/l
Class : Very soluble
Log S (Ali) : -2.23
Solubility : 1.16 mg/ml ; 0.00588 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.98
Solubility : 2.09 mg/ml ; 0.0105 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.34

Safety of [ 93-14-1 ]

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

Application In Synthesis of [ 93-14-1 ]

* 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 [ 93-14-1 ]
  • Downstream synthetic route of [ 93-14-1 ]

[ 93-14-1 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 90-05-1 ]
  • [ 106-89-8 ]
  • [ 25772-81-0 ]
  • [ 16929-60-5 ]
  • [ 93-14-1 ]
  • [ 2210-74-4 ]
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
  • 2
  • [ 2210-74-4 ]
  • [ 93-14-1 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1980, # 22, p. 1053 - 1054
[2] Journal of the American Chemical Society, 1983, vol. 105, # 3, p. 586 - 593
[3] Chemical and Pharmaceutical Bulletin, 2009, vol. 57, # 11, p. 1218 - 1222
  • 3
  • [ 90-05-1 ]
  • [ 96-24-2 ]
  • [ 93-14-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 12, p. 5071 - 5078
[2] Tetrahedron Asymmetry, 2006, vol. 17, # 21, p. 3015 - 3020
[3] Journal of the Chemical Society, 1912, vol. 101, p. 309
[4] Chimica Therapeutica, 1969, vol. 4, p. 200 - 206
[5] Journal of Medicinal Chemistry, 1995, vol. 38, # 3, p. 508 - 525
[6] Patent: WO2013/167988, 2013, A1, . Location in patent: Paragraph 0093; 0094; 0099
[7] Patent: US2015/133533, 2015, A1, . Location in patent: Paragraph 0113
  • 4
  • [ 616-30-8 ]
  • [ 90-05-1 ]
  • [ 93-14-1 ]
YieldReaction ConditionsOperation in experiment
72%
Stage #1: at 50℃; for 3 h; Reflux
Stage #2: at 90℃; for 5 h;
Equipped with a stirrer, a thermometer, a reflux condenser, a reaction vessel, 1.5mol sodium sulfite was added, the mass fraction of 20percent potassium chloride solution 300ml, controlling the stirring speed of 160 rpm, was slowly added guaiacol (2) 1.3mol, solution temperature rises to 50 , holding 3h, was added 3-amine 1,2-propanediol (3) 1.7mol, increasing the solution temperature 90 , maintained under stirring 5h, the temperature of the solution is reduced to 15 , allowed to stand for 25h after removing the aqueous layer delamination, the mass fraction of oil was added 200ml of 25percent solution of sodium bromide, mass fraction of 35percent oxalic acid solution was adjusted to maintain the pH at 7, after cooling the precipitated solid was suction filtered, washed with a solution of potassium nitrate, mass fraction washed with 70percent nitro methane in the mass fraction of 98percent propylene eye recrystallized to give crystals of 3- (o-methoxyphenoxy) -1,2-propanediol 185.33g, yield 72percent.
Reference: [1] Patent: CN105566073, 2016, A, . Location in patent: Paragraph 0013; 0014
  • 5
  • [ 556-52-5 ]
  • [ 90-05-1 ]
  • [ 14007-09-1 ]
  • [ 93-14-1 ]
YieldReaction ConditionsOperation in experiment
95% With calcined hydrotalcite In tetrahydrofuran at 120℃; for 4 h; Autoclave In a typical reaction, autoclave reactor (details included in sup-porting information) was charged with guaiacol (0.0081 mol), gly-cidol (0.020 mol), tetrahydrofuran (THF) (10 mL) and 0.03 g mL−1(0.9 g) of the catalyst. The total organic phase volume was made to30 mL with THF. An initial sample was taken at the desired temperature. The reaction mixture was stirred with mechanical stirrer atthe desired speed, and samples were collected periodically. For control reaction, speed of agitation was 1000 rpm and temperature was 120°C at self-generated pressure. Reaction samples were analyzed by HPLC (details included in supporting information). Synthesis of guaifenesin (3-(2-methoxyphenoxy)propane-1,2-diol) andbyproduct (2-(2-methoxyphenoxy)propane-1,3-diol) from condensation reaction of guaiacol and glycidol is shown in Scheme 1.
Reference: [1] Catalysis Today, 2017, vol. 291, p. 213 - 222
  • 6
  • [ 556-52-5 ]
  • [ 90-05-1 ]
  • [ 93-14-1 ]
Reference: [1] Chirality, 2016, vol. 28, # 4, p. 313 - 318
[2] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
[3] Chemical Communications, 2013, vol. 49, # 52, p. 5886 - 5888
[4] Physical Chemistry Chemical Physics, 2017, vol. 19, # 41, p. 28302 - 28312
  • 7
  • [ 90-05-1 ]
  • [ 93-14-1 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1980, # 22, p. 1053 - 1054
[2] Journal of the American Chemical Society, 1983, vol. 105, # 3, p. 586 - 593
[3] Patent: US4390732, 1983, A,
  • 8
  • [ 13052-77-2 ]
  • [ 96-24-2 ]
  • [ 93-14-1 ]
Reference: [1] Journal of the American Chemical Society, 1950, vol. 72, p. 3716
[2] Dissertationes Pharmaceuticae, 1950, vol. 2, p. 191,194, 195[3] Chem.Abstr., 1951, p. 6754
[4] Acta Chemica Scandinavica (1947-1973), 1961, vol. 15, p. 803 - 807
  • 9
  • [ 532-03-6 ]
  • [ 93-14-1 ]
Reference: [1] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2014, vol. 128, p. 263 - 271
  • 10
  • [ 90-05-1 ]
  • [ 106-89-8 ]
  • [ 25772-81-0 ]
  • [ 16929-60-5 ]
  • [ 93-14-1 ]
  • [ 2210-74-4 ]
Reference: [1] Organic Process Research and Development, 2012, vol. 16, # 10, p. 1660 - 1664
  • 11
  • [ 74-83-9 ]
  • [ 19826-87-0 ]
  • [ 93-14-1 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1960, vol. 8, p. 921 - 929
  • 12
  • [ 90-05-1 ]
  • [ 56-81-5 ]
  • [ 93-14-1 ]
Reference: [1] Green Chemistry, 2013, vol. 15, # 3, p. 625 - 628
  • 13
  • [ 532-03-6 ]
  • [ 10488-39-8 ]
  • [ 93-14-1 ]
Reference: [1] Journal of Pharmaceutical Sciences, 1994, vol. 83, # 4, p. 499 - 501
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