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Product Details of [ 21593-77-1 ]

CAS No. :21593-77-1 MDL No. :MFCD00151975
Formula : C6H11NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :ZFAHNWWNDFHPOH-YFKPBYRVSA-N
M.W : 161.22 Pubchem ID :9793905
Synonyms :
L-Deoxyalliin;S-Allylcysteine;NSC 96449

Calculated chemistry of [ 21593-77-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 42.55
TPSA : 88.62 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) : -8.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.22
Log Po/w (XLOGP3) : -2.07
Log Po/w (WLOGP) : 0.32
Log Po/w (MLOGP) : -1.93
Log Po/w (SILICOS-IT) : 0.22
Consensus Log Po/w : -0.45

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.79
Solubility : 1000.0 mg/ml ; 6.23 mol/l
Class : Highly soluble
Log S (Ali) : 0.74
Solubility : 877.0 mg/ml ; 5.44 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.3
Solubility : 81.0 mg/ml ; 0.502 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.8

Safety of [ 21593-77-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280 UN#:N/A
Hazard Statements:H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 21593-77-1 ]

* 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 [ 21593-77-1 ]
  • Downstream synthetic route of [ 21593-77-1 ]

[ 21593-77-1 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 232953-12-7 ]
  • [ 21593-77-1 ]
YieldReaction ConditionsOperation in experiment
57%
Stage #1: With trifluoroacetic acid In dichloromethane at 20℃; for 3 h; Inert atmosphere
Stage #2: With lithium hydroxide In tetrahydrofuran; water at 0 - 20℃; Cooling with ice
Example 21
S-Allylcysteine (Sac)
BocSacOMe (9.92 g, 36.02 mmol) was added to a 250 round bottom flask and dissolved in CH2Cl2 (100 mL).
The solution was placed under argon and TFA (10 mL) was added at room temperature.
The reaction was stirred at room temperature for 3 hours after which time TLC (15percent EtOAc in petrol) indicated consumption of starting material (Rf=0.4).
The solvent was then removed by rotary evaporation and the resulting yellow residue was dried briefly under vacuum.
The viscous residue was then dissolved in THF (30 mL) and the stirred solution was cooled to 0° C. LiOH (72 mL of a 5M solution) was then poured into the reaction mixture.
The ice bath was removed and the reaction stirred at room temperature for 1 hour after which time the reaction was diluted with 100 mL H2O and then neutralized (pH<7, pH paper) with DOWEX.(R). 50WX8 (H+, ~120 g).
All of the resin was poured into an empty column and washed with 500 mL of H2O (gravity flow).
The flow-through was discarded.
The product was eluted with 5percent NH4OH (aq) and the fractions containing the title compound were collected [Rf=0.6; 7:2:1 iPrOH:MeOH:NH4OH (25percent aq)].
The product was concentrated by rotary evaporation to give a yellow solid which was then purified by column chromatography [7:2:1 iPrOH:MeOH:NH4OH (25percent aq.)] to give Sac as white crystals (3.29 g, 57percent).
m.p.=212-213° C. 1H NMR (400 MHz, D2O): δH=2.5-2.70 (2H, ABX system, J=13.3, 5.3, 6.7, CH2SAllyl), 3.06 (2H, d, J=7.2, CH2CH=CH2), 3.28 (1H, dd, J=6.7, 5.3, Hα), 5.02-5.09 (2H, m, HC=CH2), 5.71 (1H, m, HC=CH2).
Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 30, p. 9642 - 9643
[2] Patent: US2012/178913, 2012, A1, . Location in patent: Page/Page column 10-11
  • 2
  • [ 52-90-4 ]
  • [ 106-95-6 ]
  • [ 21593-77-1 ]
YieldReaction ConditionsOperation in experiment
68 g
Stage #1: With sodium hydroxide In ethanol at 20℃; for 0.166667 h;
Stage #2: at 20℃; for 6 h;
(1 mol) was homogeneously dispersed in 3 L of absolute ethanol, and 3.5 mol of sodium hydroxide solution (20 mol / L) was added dropwise under magnetic stirring at room temperature and stirring was continued for 10 min. 1.1 moles of allyl bromide and reacted at room temperature for 6 h to form a crude solution of deoxythioallyl cysteine sulfoxide (2-PeCS).The solution was transferred to a clean container and adjusted to pH 5.5.4 ° C for 12 h at 30 ° C to form a white deoxy 2-PeCS crystal.(2) The 2-PeCS crystal obtained in step (1) was filtered, dried at 50 ° C, and then redissolved in 10 mL of distilled water containing 1percent glacial acetic acid and heated to boiling.The solution was poured into 150 mL of boiling ethanol and recrystallized.The solution was allowed to stand at 12 ° C for 12 h and the crystals were collected by filtration and dried at 50 ° C to give about 69 g of pure 2-PeCS.
Reference: [1] Pharmazie, 1998, vol. 53, # 10, p. 668 - 671
[2] Journal of Organic Chemistry, 1994, vol. 59, # 11, p. 3227 - 3229
[3] Organic and Biomolecular Chemistry, 2005, vol. 3, # 10, p. 2016 - 2025
[4] RSC Advances, 2016, vol. 6, # 58, p. 53519 - 53532
[5] Angewandte Chemie - International Edition, 2016, vol. 55, # 47, p. 14683 - 14687[6] Angew. Chem., 2016, vol. 128, # 47, p. 14903 - 14907,5
[7] Phytochemistry (Elsevier), 1985, vol. 24, # 7, p. 1593 - 1594
[8] Helvetica Chimica Acta, 1951, vol. 34, p. 481,486
[9] Helvetica Chimica Acta, 1948, vol. 31, p. 189,207
[10] Food and Chemical Toxicology, 2007, vol. 45, # 10, p. 2030 - 2039
[11] Patent: CN104140384, 2016, B, . Location in patent: Paragraph 0053; 0054
[12] Patent: WO2017/96450, 2017, A1, . Location in patent: Page/Page column 27
[13] Chemical Biology and Drug Design, 2016, vol. 87, # 1, p. 101 - 111
  • 3
  • [ 52-89-1 ]
  • [ 106-95-6 ]
  • [ 21593-77-1 ]
Reference: [1] Journal of Physical Chemistry B, 2011, vol. 115, # 45, p. 13408 - 13417
[2] Die Pharmazie, 1968, vol. 23, # 8, p. 462 - 467
[3] Journal of Agricultural and Food Chemistry, 2000, vol. 48, # 12, p. 6254 - 6260
[4] Journal of Organic Chemistry, 2004, vol. 69, # 19, p. 6185 - 6201
[5] Patent: US2009/36534, 2009, A1, . Location in patent: Page/Page column 9
[6] Tetrahedron, 2014, vol. 70, # 42, p. 7621 - 7626
  • 4
  • [ 1609455-99-3 ]
  • [ 21593-77-1 ]
YieldReaction ConditionsOperation in experiment
2 mg With hydrogenchloride In water at 80℃; for 18 h; During the study, 1.0 ml of a 3.0 g/l aqueous solution of 3 was treated with 10.0 mol/l HCl (1.0 ml) at 80 °C for 18 h.The mixture was immediately purified by acid cation exchange resin (Amberlite®IRP-69, Shanghai Aladdin Industrial Corporation, Shanghai, China) by using NH4OH (30percent) to afford 1 (2.0 mg), which was identified by 1H NMR and TLC and optical rotations measurement.
Reference: [1] Journal of Asian Natural Products Research, 2014, vol. 16, # 3, p. 323 - 326
  • 5
  • [ 52-90-4 ]
  • [ 107-05-1 ]
  • [ 21593-77-1 ]
Reference: [1] Patent: WO2015/8019, 2015, A1, . Location in patent: Page/Page column 82; 83
  • 6
  • [ 52-90-4 ]
  • [ 107-18-6 ]
  • [ 21593-77-1 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 6, p. 1894 - 1897
  • 7
  • [ 52-90-4 ]
  • [ 556-27-4 ]
  • [ 21593-77-1 ]
YieldReaction ConditionsOperation in experiment
2.1 mg at 80℃; for 24 h; Sealed tube Aliin(Manufactured by Funakoshi Co., Ltd.) and 24.2 mg of L-cysteine (Wako Pure Chemical Industries, Ltd.) were dissolved in 10 mL of water, placed in a plastic container, sealed, kept at 80 ° C. and reacted for 24 hours . After completion of the reaction, this solution was measured using LC / TOF-MS (microTOF 2-kp manufactured by Bruker-Dartonics) to find a mass of 162.0583 as [M + H] + to produce S-allyl cysteine It was confirmed that it was doing. The content of S-allyl cysteine in the aqueous solution was analyzed by HPLC, and it was 0.28 mg / ml. Furthermore, S-allyl cysteine was purified from this aqueous solution using preparative HPLC to obtain 2.1 mg of a white powder, and its purity was analyzed by HPLC,It was 98percent
Reference: [1] Patent: JP2015/140348, 2015, A, . Location in patent: Paragraph 0032
  • 8
  • [ 18598-63-5 ]
  • [ 106-95-6 ]
  • [ 21593-77-1 ]
Reference: [1] Bioscience, Biotechnology and Biochemistry, 2018, vol. 82, # 4, p. 724 - 731
  • 9
  • [ 124773-55-3 ]
  • [ 21593-77-1 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 14, p. 5929 - 5941
  • 10
  • [ 870-23-5 ]
  • [ 5147-00-2 ]
  • [ 21593-77-1 ]
Reference: [1] Phytochemistry (Elsevier), 1986, vol. 25, # 12, p. 2759 - 2764
[2] Phytochemistry (Elsevier), 1988, vol. 27, # 7, p. 2011 - 2016
  • 11
  • [ 870-23-5 ]
  • [ 407-41-0 ]
  • [ 21593-77-1 ]
Reference: [1] Chemistry Letters, 2017, vol. 46, # 12, p. 1789 - 1792
  • 12
  • [ 870-23-5 ]
  • [ 52-90-4 ]
  • [ 21593-77-1 ]
Reference: [1] Phytochemistry (Elsevier), 1988, vol. 27, # 7, p. 2011 - 2016
  • 13
  • [ 870-23-5 ]
  • [ 2731-73-9 ]
  • [ 21593-77-1 ]
Reference: [1] Agricultural and Biological Chemistry, 1981, vol. 45, # 1, p. 259 - 264
  • 14
  • [ 556-27-4 ]
  • [ 21593-77-1 ]
Reference: [1] Helvetica Chimica Acta, 1948, vol. 31, p. 189,207
  • 15
  • [ 49621-03-6 ]
  • [ 21593-77-1 ]
Reference: [1] Helvetica Chimica Acta, 1948, vol. 31, p. 189,207
  • 16
  • [ 21593-77-1 ]
  • [ 556-27-4 ]
YieldReaction ConditionsOperation in experiment
3.3 g With dihydrogen peroxide In water at 20℃; for 12 h; Pure 2-PeCS (0.2 mol) obtained in step (2) was dissolved in 250 mL of distilled water, 0.28 mol of a hydrogen peroxide solution (30percent) was slowly added with magnetic stirring, and stirring was continued at room temperature for 12 h to obtain crude 2- PeCSO solution.The insoluble impurities in the solution were removed by filtration, and then 2 L of anhydrous ethanol was added and 6 ° C was placed at 4 ° C to form 2-PeCSO crystals.The crystals were filtered to dry at 40 ° C to give 33.6 g of thioallyl cysteine sulfoxide (2-PeCSO).(4) The 2-PeCSO crystal obtained in step (3) was dissolved in 150 mL of distilled water, heated to 50 ° C, and a first dilute acetone solution (96 mL of distilled water + 492 mL of acetone) at 50 ° C was added and cooled to room temperature.The solution was allowed to stand at 4 ° C for 12 h.(8.2.4 mL of distilled water + 112 mL of acetone) was added at 50 ° C, the mixture was filtered hot, cooled to room temperature, and the solution was allowed to stand at 4 ° C for 12 hours to crystallize.(11 mL of distilled water + 50 mL of acetone) at 50 ° C, and the mixture was filtered through hot, cooled to room temperature, and the solution was allowed to stand at 4 ° C for 12 hours to give pure crystals. The solution was purified by filtration and dried in 15 mL of distilled water. (+) 2-PeCSO about 3.3g.
Reference: [1] Molecular Pharmacology, 1997, vol. 51, # 3, p. 507 - 515
[2] Helvetica Chimica Acta, 1951, vol. 34, p. 481,486
[3] Helvetica Chimica Acta, 1948, vol. 31, p. 189,207
[4] Journal of Agricultural and Food Chemistry, 2000, vol. 48, # 11, p. 5731 - 5735
[5] Journal of Agricultural and Food Chemistry, 2000, vol. 48, # 12, p. 6254 - 6260
[6] Die Pharmazie, 1968, vol. 23, # 8, p. 462 - 467
[7] Tetrahedron, 1972, vol. 28, p. 4503 - 4513
[8] Journal of Molecular Structure, 2013, vol. 1035, p. 421 - 426
[9] Patent: WO2015/8019, 2015, A1, . Location in patent: Page/Page column 83
[10] Patent: CN104140384, 2016, B, . Location in patent: Paragraph 0055; 0056
[11] Bioscience, Biotechnology and Biochemistry, 2018, vol. 82, # 4, p. 724 - 731
[12] Journal of Agricultural and Food Chemistry, 2018, vol. 66, # 40, p. 10506 - 10512
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