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Chemical Structure| 57-10-3
Chemical Structure| 57-10-3
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Product Details of [ 57-10-3 ]

CAS No. :57-10-3 MDL No. :MFCD00002747
Formula : C16H32O2 Boiling Point : -
Linear Structure Formula :- InChI Key :IPCSVZSSVZVIGE-UHFFFAOYSA-N
M.W : 256.42 Pubchem ID :985
Synonyms :
Hexadecanoic acid;Cetylic acid;NSC 5030;C16:0 Fatty acid
Chemical Name :Hexadecanoic acid

Calculated chemistry of [ 57-10-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.94
Num. rotatable bonds : 14
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 80.8
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -2.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.85
Log Po/w (XLOGP3) : 7.17
Log Po/w (WLOGP) : 5.55
Log Po/w (MLOGP) : 4.19
Log Po/w (SILICOS-IT) : 5.25
Consensus Log Po/w : 5.2

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.02
Solubility : 0.00243 mg/ml ; 0.00000949 mol/l
Class : Moderately soluble
Log S (Ali) : -7.77
Solubility : 0.00000431 mg/ml ; 0.0000000168 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -5.31
Solubility : 0.00125 mg/ml ; 0.00000488 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.31

Safety of [ 57-10-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 57-10-3 ]

* 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 [ 57-10-3 ]
  • Downstream synthetic route of [ 57-10-3 ]

[ 57-10-3 ] Synthesis Path-Upstream   1~21

  • 1
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  • [ 50-81-7 ]
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YieldReaction ConditionsOperation in experiment
91.3%
Stage #1: at 18℃; for 15 h;
Stage #2: at 28℃; for 20 h;
(1)500g of concentrated sulfuric acid was added to the three-necked flask, add 50g of palmitic acid, stirring to dissolve Solution in concentrated sulfuric acid was added 50gL- ascorbic acid, 18 ° C reaction 15h; (2)50g palmitic anhydride was added to the reaction mixture, the temperature was raised to 28 ° C, the reaction 20h, then After adding 10g of activated carbon and stirred for 15min; (3)The step (2) in the resulting mixture is added to 1250ml10 ° C cold water, filtered The filter cake is too crude, the crude product was rinsed with 100ml water, then washed with water after the crude product was dissolved in 750ml of butyl acetate, 50 ° C incubation decolorization 30min. Filtered and allowed to stand, stratification, the upper organic layer (Product containing layer) 50 ° C, washed twice with water, water per 500ml. After washing to the water layer, The organic layer was distilled off under reduced pressure to 400ml of butyl acetate, allowed to stand for cooling to 15 ° C, the solid was filtered off with 50ml The resulting solid was rinsed with ethyl acetate, drained, placed in a vacuum drying oven at 50 ° C. L-ascorbic acid-6-palmitate was obtained as a white flake with a purity of 98. 1percent and a yield of 91.3percent.
Reference: [1] Patent: CN105315244, 2016, A, . Location in patent: Paragraph 0047-0050
  • 2
  • [ 57-10-3 ]
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  • [ 137-66-6 ]
Reference: [1] JAOCS, Journal of the American Oil Chemists' Society, 2003, vol. 80, # 8, p. 795 - 799
[2] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 102, p. 127 - 131
[3] Ultrasonics Sonochemistry, 2011, vol. 18, # 5, p. 988 - 996
[4] JAOCS, Journal of the American Oil Chemists' Society, 2011, vol. 88, # 1, p. 57 - 64
[5] Oil and Soap (Alexandria, Egypt), 1943, vol. 20, p. 224
[6] Annales Pharmaceutiques Francaises, 1957, vol. 15, p. 691,693
[7] JAOCS, Journal of the American Oil Chemists' Society, 1999, vol. 76, # 11, p. 1291 - 1295
[8] Farmaco, 2003, vol. 58, # 12, p. 1271 - 1276
[9] Journal of Physical Chemistry B, 2014, vol. 118, # 11, p. 3053 - 3062
[10] Patent: CN103254160, 2016, B, . Location in patent: Paragraph 0017-0022
  • 3
  • [ 13182-85-9 ]
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  • [ 443-48-1 ]
Reference: [1] Pharmazie, 2000, vol. 55, # 5, p. 369 - 371
  • 4
  • [ 555-44-2 ]
  • [ 4704-94-3 ]
  • [ 57-10-3 ]
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 102, p. 16 - 24
  • 5
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YieldReaction ConditionsOperation in experiment
95.7%
Stage #1: With triethylamine; diisopropyl-carbodiimide In dichloromethane at 20℃; for 4 h;
Stage #2: at 20℃; for 0.5 h; Inert atmosphere
1) under nitrogen at room temperature,Triethylamine (2 ml) was added dropwise to mercaptomethyl resin (2 g,MATRIX-INN), N-hydroxy maleimide (1.1 g, 9.7 mmol) and DMF (40 ml)In the reaction vessel.After stirring at room temperature for 24 hours,Afterwards, stirring was continued for 4 hours at 55 degrees,After cooling to room temperature and filtered to give NHS resin,Using DMF,Distilled water and isopropyl alcohol were washed twice,NHS resin was obtained after vacuum drying.2) palmitic acid (1.465 g, 5.72 mmol) and the above NHS resin (1.50 g),DIC (diisopropylcarbodiimidediisoprpylcarbodiimide, 0.72 g, 5.72 mmol),Triethylamine (2 ml) was suspended in 15 ml of dichloromethane.The mixture was stirred at room temperature for 4 hours.Then filtered (filtrate retained,Appropriate amount of palmitic acid was detected by HPLC,DIC and solvent,For the next batch of reactions),The collected resin using DMF,Water, isopropanol, and dichloromethane were separately washed twice and dried in vacuo to give 1.70 g of dry resin to obtain an immobilized palmitic acid active ester with a loading of -1.0 mmol / g.3) Ethanolamine (93.2 mg, 1.58 mmol) was added to a flask containing active ester (1.75 g) and 50 ml of BAlcohol suspension,For 0.5 hour,Centrifugal removal of solid resin,The resin was washed twice with ethanol (the resin was left after vacuum drying)The combined liquid phase was concentrated under reduced pressure,453 mg of palmitic monoethanolamide (96.6percent yield for ethanolamine) was obtained,Purity> 99.5percent (HPLC).
90%
Stage #1: With 1-[(1-(cyano-​2-​ethoxy-​2-​oxoethylidenaminooxy)​dimethylamino-​morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 20℃; for 0.166667 h; Inert atmosphere
Stage #2: at 20℃; Inert atmosphere
General procedure: These compounds were synthesized according to the procedure described previously with slight modifications (El-Faham and Albericio, 2010) The appropriate acid (0.15 mmol), (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluoro phosphate (COMU, 64.2 mg, 0.15 mmol), and DIPEA (0.05 ml, 0.30 mmol) were dissolved in anhydrous CH2Cl2 (0.5 ml) and CH3CN (2.5 ml) and the resulting orange-red solution was stirred at rt for 10 min under a nitrogen atmosphere. Ethanolamine (3) (0.15 mmol) in CH3CN (0.2 ml) was then injected into the reaction mixture and vigorous stirring at rt was continued until TLC (CH2Cl2/MeOH 98:2) confirmed the completion of the reaction (3–6 h). The reaction mixture was diluted with CH2Cl2 (3 ml) and the resulting mixture was washed with 5percent HCl, saturated NaHCO3 and brine. The organic layer was collected, dried over anhydrous Na2SO4, filtered. The solvent was evaporated under reduced pressure and crude purified by flash chromatography.
72% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 4 h; Inert atmosphere Stepl . Palmitoylethanolamide, 2: EDCl (673 mg, 3.51 mmol), DMAP (44 mg, 0.35 mmol), and ethanolamine (0.141 mL, 2.34 mmol) were added to a solution palmitic acid 1 (300 mg, 1.17 mmol) was stirred in 10 mL of anhydrous ΟΗ2( at 0 °C. The reaction was allowed to stir under argon for 4 hours while warming to room temperature. Upon completion the reaction mixture was diluted with CH2C, washed with water and brine. The organic layer was collected and concentrated. The resulting residue was chromatographed on silica to yield 2 (312 mg, 72percent) as a white solid. XH NMR (500 MHz, CDC13) δ 3.70 - 3.76 (m, 2H), 3.43 (q, J = 5.37 Hz, 2H), 2.17 - 2.24 (m, 2H), 1.64 (quin, J = 7.45 Hz, 2H), 1.52 (d, J = 1.0 Hz, 1H), 1.19 - 1.35 (m, 26H).
Reference: [1] Beilstein Journal of Organic Chemistry, 2009, vol. 5,
[2] Patent: CN107188816, 2017, A, . Location in patent: Paragraph 0048-0052
[3] Chemistry and Physics of Lipids, 2012, vol. 165, # 7, p. 705 - 711
[4] Patent: WO2015/179190, 2015, A1, . Location in patent: Paragraph 0137
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3231 - 3234
[6] Patent: US5925678, 1999, A,
[7] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 4, p. 1520 - 1527
[8] Bioscience, Biotechnology and Biochemistry, 2011, vol. 75, # 4, p. 768 - 770
[9] ChemSusChem, 2015, vol. 8, # 16, p. 2670 - 2680
[10] Green Chemistry, 2018, vol. 20, # 2, p. 375 - 381
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Reference: [1] Tetrahedron Letters, 1980, vol. 21, p. 841 - 844
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 2, p. 340 - 347
[3] Medicinal Chemistry Research, 2017, vol. 26, # 11, p. 2951 - 2966
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YieldReaction ConditionsOperation in experiment
98.3 %Chromat. With tungsten oxide impregnated Zr incorporated mesoporous silica SBA-15 In 1,3,5-trimethyl-benzene at 162℃; for 6 h; Inert atmosphere; Dean-Stark Cetyl alcohol (CA) and palmitic acid (PA) esterification reactions were performed under N2 atmosphere in a four necked round bot-tom flask (250 ml) equipped with a Teflon coated magnetic stirring bar with a stirring rate of 520 rpm and a Dean Stark apparatus surmounted with a reflux condenser. In a typical experiment, 160 mgof catalyst was added into 25 ml of mesitylene and heated up to reaction temperature of 162 C. An equimolar solution of palmitic acid and cetyl alcohol (6 mmol) in 15 ml of mesitylene at room temperature was added into the reactor. All the reactions were carried out for a reaction time of 6 h. In a preliminary set of experiments (Table 1) it was found that the reaction was not controlled by external diffusion at 520 rpm. Samples taken at regular intervals were analyzed by Agilent 6890 gas chromatography using Ultra 1(25 m × 0.3 mm) capillary column equipped with FID. The injector temperature was 280C and the detector temperature was 320 C.The GC oven temperature was changed from 50C at 12C/min to 300C where it was kept for 35 min. Helium was used as the car-rier gas at a flow rate of 37.3 ml/min The split ratio was 24.9:1. Conversion of cetyl alcohol (CA), yield of cetyl palmitate (CP) and the selectivity to CP were defined as below. Conversion(percent)= (CAin −CAout )CAin×100 Yield(percent)= CPoutCAin×100 Selectivity to CP(percent) = CPout(CAin −CAout )×100
Reference: [1] Synthesis, 2005, # 12, p. 1939 - 1944
[2] Chemistry Letters, 2005, vol. 34, # 11, p. 1502 - 1503
[3] Tetrahedron Letters, 2007, vol. 48, # 39, p. 6962 - 6965
[4] Agricultural and Biological Chemistry, 1988, vol. 52, # 11, p. 2933 - 2936
[5] Synthetic Communications, 1986, vol. 16, p. 1423 - 1430
[6] Biochemische Zeitschrift, 1931, vol. 241, p. 467
[7] Biochemische Zeitschrift, 1933, vol. 259, p. 424
[8] Biochemische Zeitschrift, 1933, vol. 259, p. 424
[9] Journal of the American Pharmaceutical Association (1912-1977), 1944, vol. 33, p. 107[10] Chem.Abstr., 1944, p. 2765
[11] Agricultural and Biological Chemistry, 1988, vol. 52, # 10, p. 2631 - 2632
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[13] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
[14] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
[15] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 3-4
[16] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
[17] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
[18] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
[19] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
[20] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
[21] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
[22] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
[23] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
[24] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
[25] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 7
[26] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 8-9
[27] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 7
[28] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 21-22
[29] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 13
[30] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 13
[31] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 19-20
[32] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[33] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[34] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[35] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[36] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[37] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[38] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[39] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 7
[40] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[41] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[42] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[43] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[44] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[45] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[46] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[47] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[48] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[49] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 7
[50] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 16-17
[51] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 16-17
[52] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 9
[53] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 9
[54] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 9
[55] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 9
[56] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 8-9
[57] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10-11
[58] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10-11
[59] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10-11
[60] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10-11
[61] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10-11
[62] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10-11
[63] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 8-9
[64] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10-11
[65] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10-11
[66] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10-11
[67] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10-11
[68] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10-11
[69] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10-11
[70] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10-11
[71] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 8-9
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[2] Patent: US1997172, 1934, ,
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[2] Patent: US2005/33070, 2005, A1, . Location in patent: Page/Page column 1-2
[3] Patent: US2005/33070, 2005, A1, . Location in patent: Page/Page column 2
[4] Patent: US2005/33070, 2005, A1, . Location in patent: Page/Page column 2
[5] Patent: US2005/33070, 2005, A1, . Location in patent: Page/Page column 2
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[2] Chemistry - A European Journal, 2013, vol. 19, # 15, p. 4732 - 4741
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YieldReaction ConditionsOperation in experiment
78% With Novozyme 435 (from Candida antarctica immobilized on acrylic resin); Amberlyst A-21 In toluene at 20℃; for 15 h; Enzymatic reaction Example 28; Preparation of Retinyl Palmitate in the Presence of Amberlyst A-21; Retinyl acetate (1.00 g; 3.04 mmol) was dissolved in 8.5 mL of toluene and palmitic acid (1.56 g; 6.09 mmol; 2.0 equiv) was added followed by 120 mg of Novozyme 435 and 0.5g of dried Amberlyst A-21. The reaction mixture was stirred at RT for 15 h, at which point a sample was removed and analyzed by HPLC, indicating 89.2percent conversion to retinyl palmitate with 9.1percent retinyl acetate and 1.7percent retinol. The reaction mixture was filtered and concentrated, then concentrated twice with heptane (10 mL each). The residue was dissolved in heptane (15 mL) and washed with 2.x.20 mL with a 1:1 mixture of 10percent aqueous potassium carbonate and methanol. The organic layer was washed further with a mixture of saturated sodium bicarbonate (2.5 mL), water (7.5 mL), and methanol (10 mL), dried (sodium sulfate) and concentrated to afford 1.25 g (78percent) of a yellow oil. Analysis of this product indicated 91.2percent retinyl palmitate (HPLC area percent), 0.4 wt percent palmitic acid, and 0.2percent retinol. HPLC (4.6.x.150 mm Zorbax SB-C8 column [Agilent], 3.5μ thickness, methanol eluent, detection at 350 nm): tR 5.52 min (retinyl palmitate); tR 2.32 min (retinyl acetate); tR 2.08 min (retinol).
Reference: [1] Patent: US7566795, 2009, B2, . Location in patent: Page/Page column 11
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[2] Bulletin des Societes Chimiques Belges, 1963, vol. 72, p. 239 - 254
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[8] Journal of Biological Chemistry, 1949, vol. 177, p. 143,147
[9] Biochim. Terap. sperim., 1938, vol. 25, p. 207,209
[10] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1935, vol. 236, p. 69,71[11] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1936, vol. 239, p. 165
[12] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1940, vol. 263, p. 73,76
  • 21
  • [ 57-10-3 ]
  • [ 601-34-3 ]
Reference: [1] Lipids, 2015, vol. 50, # 6, p. 611 - 620
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