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[ CAS No. 326-91-0 ] {[proInfo.proName]}

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Chemical Structure| 326-91-0
Chemical Structure| 326-91-0
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Product Citations

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Panse, Nimishraj ; Halquist, Matthew ; Gerk, Phillip M. DOI: PubMed ID:

Abstract: Ketone ester ((R)-3-hydroxybutyl (R)-3-hydroxybutyrate) has gained popularity as an exogenous means to achieve ketosis. Regarding its potential as a therapeutic prodrug, it will be necessary to study its pharmacokinetic profile and its proximal metabolites (beta-hydroxybutyrate, 1,3-butanediol and acetoacetate) in humans. Here we develop and validate two LC-MS methods for quantifying KE and its metabolites in human plasma. The first assay uses a C18 column to quantitate ketone ester, beta-hydroxybutyrate and 1,3-butanediol, and the second assay uses a hydrophilic interaction liquid chromatog. (HILIC) column for the quantitation of acetoacetate. The method was partially validated for intra- and inter-day accuracy and precision based on the ICH M10 guidelines. For both the assays, the intra- and inter-run accuracy was ±15% of the nominal concentration and the precision (%CV) was <15% for all 4 mols. being quantified. The matrix effect for all mols. was evaluated and ranged from -62.1 to 44.4% (combined for all mols.), while the extraction recovery ranged from 65.1 to 119% (combined for all mols.). Furthermore, the metabolism of ketone ester in human plasma and human serum albumin was studied using the method. Non-saturable metabolism of ketone ester was seen in human plasma at concentrations as high as 5 mM and human serum albumin contributed to the metabolism of ketone ester. Together, these assays can be used to track the entire kinetics of ketone ester and its proximal metabolites. The reverse-phase method was used to study the metabolic profile of KE in human plasma and the plasma protein binding of 1,3-BD.

Keywords: bioanalysis ; human plasma ; ketone bodies ; ketone ester ; LC-MS

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Product Details of [ 326-91-0 ]

CAS No. :326-91-0 MDL No. :
Formula : C8H5F3O2S Boiling Point : -
Linear Structure Formula :- InChI Key :TXBBUSUXYMIVOS-UHFFFAOYSA-N
M.W : 222.18 Pubchem ID :5601
Synonyms :
HTTA;TTA;Thenoyltrifluoroacetone;NSC 405706;NSC 405705;NSC 405704;NSC 405703;NSC 405702;NSC 66544;TTFA

Calculated chemistry of [ 326-91-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.25
Num. rotatable bonds : 4
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.52
TPSA : 62.38 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.53
Log Po/w (XLOGP3) : 1.46
Log Po/w (WLOGP) : 3.71
Log Po/w (MLOGP) : 0.89
Log Po/w (SILICOS-IT) : 3.64
Consensus Log Po/w : 2.25

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.14
Solubility : 1.62 mg/ml ; 0.00728 mol/l
Class : Soluble
Log S (Ali) : -2.38
Solubility : 0.934 mg/ml ; 0.00421 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.86
Solubility : 0.305 mg/ml ; 0.00137 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.08

Safety of [ 326-91-0 ]

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 [ 326-91-0 ]

* 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 [ 326-91-0 ]
  • Downstream synthetic route of [ 326-91-0 ]

[ 326-91-0 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 88-15-3 ]
  • [ 383-63-1 ]
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YieldReaction ConditionsOperation in experiment
32%
Stage #1: With sodium methylate In methanol at 0 - 20℃; for 1 h;
Stage #2: at 80℃;
1- (thiophen-2-yl) ethanone (20g, 16mmol) was added to a solution of NaOMe (10.3g, 19mmol ) in MeOH at 0 dropwise, and the mixture was stirred at room temperature for 1hr. Then the mixture was cooled to 0, and ethyl 2, 2, 2-trifluoroacetate (27g, 19mmol) was added in portions, and the whole reaction mixture was stirred and refluxed at 80 overnight. After the organic solvent was evaporated in vacuo, the risidue was dissolved in H2O (200mL) , acified by HCl (120mL, 1N) , and extracted by EtOAc (200mL) 3 times. The organic layer was combined, washed with brine, dried over Na2SO4, concentrated and further purified by silica gel column chromatography (PE/EA 20/1) , to give 11g of 4, 4, 4-trifluoro-1- (thiophen-2-yl) butane-1, 3-dione (1-01) as a light red solid (32) .
Reference: [1] Synthesis, 1997, # 11, p. 1321 - 1324
[2] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 4, p. 407 - 412
[3] Patent: WO2018/14802, 2018, A1, . Location in patent: Paragraph 0122
[4] Journal of the American Chemical Society, 1950, vol. 72, p. 2948,2949
[5] Patent: US2723982, 1949, ,
[6] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 2, p. 343 - 346
[7] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 14, p. 4750 - 4760
[8] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 15, p. 5370 - 5383
[9] Russian Journal of General Chemistry, 2007, vol. 77, # 10, p. 1732 - 1741
[10] Chemistry of Heterocyclic Compounds, 2008, vol. 44, # 5, p. 606 - 614[11] Khim. Geterotsikl. Soedin., 2008, # 5, p. 765 - 775,11
[12] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 6, p. 1581 - 1588
[13] Advanced Synthesis and Catalysis, 2015, vol. 357, # 14-15, p. 3076 - 3080
[14] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 545 - 551
[15] European Journal of Medicinal Chemistry, 2018, vol. 152, p. 307 - 317
  • 2
  • [ 407-25-0 ]
  • [ 326-91-0 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 48, p. 8701 - 8705
  • 3
  • [ 615-07-6 ]
  • [ 98-03-3 ]
  • [ 527-72-0 ]
  • [ 326-91-0 ]
  • [ 76-05-1 ]
Reference: [1] Journal of Photochemistry and Photobiology A: Chemistry, 2018, vol. 364, p. 303 - 308
  • 4
  • [ 407-25-0 ]
  • [ 326-91-0 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 48, p. 8701 - 8705
  • 5
  • [ 88-15-3 ]
  • [ 407-38-5 ]
  • [ 326-91-0 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 3, p. 402 - 409
  • 6
  • [ 148-24-3 ]
  • [ 55954-78-4 ]
  • [ 326-91-0 ]
Reference: [1] Inorganica Chimica Acta, 2003, vol. 342, p. 97 - 106
  • 7
  • [ 59354-21-1 ]
  • [ 326-91-0 ]
Reference: [1] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1993, # 2, p. 313 - 318
  • 8
  • [ 59354-21-1 ]
  • [ 15788-02-0 ]
  • [ 326-91-0 ]
Reference: [1] South African Journal of Chemistry, 2008, vol. 61, p. 13 - 21
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