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Chemical Structure| 56-81-5 Chemical Structure| 56-81-5
Chemical Structure| 56-81-5

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Glycerol is a versatile chemical commonly used in sample preparation and gel formation in polyacrylamide gel electrophoresis.

Synonyms: Trihydroxypropane; Glycerin; NSC 9230

4.5 *For Research Use Only !

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Product Citations

Product Citations

Xiao, Xu ; Kim, Youngjae ; Romartinez-Alonso, Beatriz ; Sirvydis, Kristupas ; Ory, Daniel S. ; Schwabe, John W. R. , et al.

Abstract: The Aster proteins (encoded by the Gramd1a-c genes) contain a ligand-binding fold structurally similar to a START domain and mediate nonvesicular plasma membrane (PM) to endoplasmic reticulum (ER) cholesterol transport. In an effort to develop small mol. modulators of Asters, we identified 20α-hydroxycholesterol (HC) and U18666A as lead compounds Unfortunately, both 20α-HC and U18666A target other sterol homeostatic proteins, limiting their utility. 20α-HC inhibits sterol regulatory element-binding protein 2 (SREBP2) processing, and U18666A is an inhibitor of the vesicular trafficking protein Niemann-Pick C1 (NPC1). To develop potent and selective Aster inhibitors, we synthesized a series of compounds by modifying 20α-HC and U18666A. Among these, AI (Aster inhibitor)-1l, which has a longer side chain than 20α-HC, selectively bound to Aster-C. The crystal structure of Aster-C in complex with AI-1l suggests that sequence and flexibility differences in the loop that gates the binding cavity may account for the ligand specificity for Aster C. We further identified the U18666A analog AI-3d as a potent inhibitor of all three Aster proteins. AI-3d blocks the ability of Asters to bind and transfer cholesterol in vitro and in cells. Importantly, AI-3d also inhibits the movement of low-d. lipoprotein (LDL) cholesterol to the ER, although AI-3d does not block NPC1. This finding positions the nonvesicular Aster pathway downstream of NPC1-dependent vesicular transport in the movement of LDL cholesterol to the ER. Selective Aster inhibitors represent useful chem. tools to distinguish vesicular and nonvesicular sterol transport mechanisms in mammalian cells.

Keywords: cholesterol ; lipid metabolism ; lipid transport

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Product Details of Glycerol

CAS No. :56-81-5
Formula : C3H8O3
M.W : 92.09
SMILES Code : OCC(O)CO
Synonyms :
Trihydroxypropane; Glycerin; NSC 9230
MDL No. :MFCD00004722
InChI Key :PEDCQBHIVMGVHV-UHFFFAOYSA-N
Pubchem ID :753

Safety of Glycerol

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H319
Precautionary Statements:P264-P337+P313-P305+P351+P338

Application In Synthesis of Glycerol

* 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 [ 56-81-5 ]
  • Downstream synthetic route of [ 56-81-5 ]

[ 56-81-5 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 57-50-1 ]
  • [ 57-48-7 ]
  • [ 50-99-7 ]
  • [ 56-81-5 ]
  • [ 470-69-9 ]
  • [ 13133-07-8 ]
References: [1] Journal of Agricultural and Food Chemistry, 2008, vol. 56, # 8, p. 2805 - 2809.
  • 2
  • [ 626-40-4 ]
  • [ 56-81-5 ]
  • [ 34522-69-5 ]
YieldReaction ConditionsOperation in experiment
56%
Stage #1: at 120℃;
Stage #2: at 130℃;
Step 1: A 100 mL flask was charged with 3,5-dibromoaniline (5.00 g, 19.9 mmol), sodium 3-nitrobenzenesulfonate (987 mg, 4.39 mmol), iron(ll)sulfate heptahydrate (63.2 mg, 0.658 mmol), and methanesulfonic acid (20 mL). A reflux condenser was added, and the reaction was heated in a 120 °C aluminum block.Glycerol (0.64 mL, 8.8 mmol) was added through the condenser, and the aluminum block temperature was then increased to 130 °C. Heating was continued overnight. After cooling to rt, the reaction mixture was diluted with DCM and water, cooled in an ice/water bath, and rendered alkaline by addition of a 50percent aqueous solution of NaOH. The resulting mixture was filtered over Celite® and extracted with DCM. The organicphase was dried over Na2SO4 and concentrated to a brown solid. Purification by chromatography (80 g Si gel, 0—40percent EtOAc in heptane gradient over 17 CV and then held at 40percent) afforded 5,7-dibromoquinoline as a tan solid (3.19 g, 56percent). 1H NMR (400 MHz, CDCI3) O 7.53 (dd, 1 H), 7.96 (d, 1 H), 8.29 (d, 1 H), 8.50 (d, 1 H), 8.93 (dd, 1 H). LCMS (ESI) m/z: 285.9 [M+H] (95percent). LCMS data were acquired from the reactionmixture immediately prior to workup.
References: [1] Patent: WO2016/103097, 2016, A1, . Location in patent: Page/Page column 59; 60.
[2] Journal fuer Praktische Chemie (Leipzig), 1889, vol. <2> 40, p. 380.
  • 3
  • [ 78-90-0 ]
  • [ 56-81-5 ]
  • [ 123-32-0 ]
  • [ 108-50-9 ]
  • [ 77164-93-3 ]
References: [1] Chinese Chemical Letters, 2013, vol. 24, # 8, p. 751 - 754.
  • 4
  • [ 78-90-0 ]
  • [ 56-81-5 ]
  • [ 108-50-9 ]
  • [ 77164-93-3 ]
  • [ 108-49-6 ]
References: [1] Catalysis Science and Technology, 2017, vol. 7, # 15, p. 3399 - 3407.
[2] New Journal of Chemistry, 2017, vol. 41, # 18, p. 9875 - 9883.
  • 5
  • [ 78-90-0 ]
  • [ 56-81-5 ]
  • [ 123-32-0 ]
  • [ 61892-95-3 ]
  • [ 108-50-9 ]
  • [ 77164-93-3 ]
References: [1] Chinese Chemical Letters, 2013, vol. 24, # 8, p. 751 - 754.
  • 6
  • [ 78-90-0 ]
  • [ 56-81-5 ]
  • [ 108-50-9 ]
  • [ 77164-93-3 ]
References: [1] Catalysis Science and Technology, 2017, vol. 7, # 15, p. 3399 - 3407.
  • 7
  • [ 334-48-5 ]
  • [ 56-81-5 ]
  • [ 60514-49-0 ]
  • [ 2277-23-8 ]
  • [ 17598-93-5 ]
  • [ 172588-12-4 ]
References: [1] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 100, p. 7 - 18.
  • 8
  • [ 334-48-5 ]
  • [ 56-81-5 ]
  • [ 60514-49-0 ]
  • [ 621-71-6 ]
  • [ 2277-23-8 ]
  • [ 17598-93-5 ]
  • [ 172588-12-4 ]
References: [1] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 100, p. 7 - 18.
  • 9
  • [ 110-42-9 ]
  • [ 56-81-5 ]
  • [ 2277-23-8 ]
  • [ 17863-69-3 ]
  • [ 17598-93-5 ]
References: [1] Green Chemistry, 2013, vol. 15, # 3, p. 786 - 797.
  • 10
  • [ 2082-76-0 ]
  • [ 56-81-5 ]
  • [ 2277-23-8 ]
References: [1] Tetrahedron Asymmetry, 2004, vol. 15, # 22, p. 3551 - 3559.
  • 11
  • [ 334-48-5 ]
  • [ 56-81-5 ]
  • [ 2277-23-8 ]
References: [1] Green Chemistry, 2017, vol. 19, # 2, p. 390 - 396.
  • 12
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  • [ 56-81-5 ]
  • [ 621-71-6 ]
  • [ 2277-23-8 ]
  • [ 17863-69-3 ]
  • [ 17598-93-5 ]
References: [1] JAOCS, Journal of the American Oil Chemists' Society, 1999, vol. 76, # 7, p. 839 - 843.
  • 13
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  • [ 621-71-6 ]
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  • [ 17598-93-5 ]
References: [1] JAOCS, Journal of the American Oil Chemists' Society, 1996, vol. 73, # 11, p. 1521 - 1525.
[2] JAOCS, Journal of the American Oil Chemists' Society, 2014, vol. 91, # 2, p. 261 - 270.
  • 14
  • [ 110-38-3 ]
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  • [ 621-71-6 ]
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  • [ 3376-48-5 ]
  • [ 17863-69-3 ]
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References: [1] JAOCS, Journal of the American Oil Chemists' Society, 1996, vol. 73, # 11, p. 1489 - 1495.
  • 15
  • [ 20776-50-5 ]
  • [ 56-81-5 ]
  • [ 928839-62-7 ]
References: [1] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8217 - 8231.
  • 16
  • [ 6933-10-4 ]
  • [ 56-81-5 ]
  • [ 122759-89-1 ]
YieldReaction ConditionsOperation in experiment
25% With sulfuric acid; sodium 3-nitrobenzenesulfonate In water at 120 - 130℃; for 1.5 h; The raw materials 3,5-difluoroaniline G-1 (5.6 g, 27 mmol) and sodium 3-nitrobenzenesulfonate (7.2 g, 32 mmol) Was added to a mixed solution of concentrated sulfuric acid (15 mL) and water (6 mL) After heating to an internal temperature of 120 ° C, glycerol (7.4 g, 80 mmol) After the addition was completed, the temperature was raised to 130 ° C and reacted for 1.5h, then cooled. The reaction was poured into crushed ice, concentrated ammonia water to adjust the pH to 5 ~ 6, the precipitated solid was filtered off, washed with water, After drying, column chromatography gave 3.82 g of white solid compound G-2 in 58percent yield. A mixture of 6-bromo-7-methylquinoline (I-2) and 6-bromo-5-methylquinoline (J-1) was synthesized. Then separated by supercritical preparative chromatography (SFC), IC-H column, mobile phase: isopropanol / carbon dioxide = 18/82, detection wavelength: 254nm. The first fraction was collected as 6-bromo-7-methylquinoline (I-2) as a white solid, yield: 25percent. The second fraction was collected as a 6-bromo-5-methylquinoline (J-1) white solid in a yield of 20percent
References: [1] Patent: CN105968115, 2016, A, . Location in patent: Paragraph 0492; 0518-0520.
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4281 - 4290.
  • 17
  • [ 6933-10-4 ]
  • [ 56-81-5 ]
  • [ 122759-89-1 ]
YieldReaction ConditionsOperation in experiment
31%
Stage #1: With iron(III) sulfate; sulfuric acid In nitrobenzene for 3 h; Heating / reflux
Stage #2: With water; sodium hydrogencarbonate In nitrobenzene
Intermediate 4: 6-Bromo-7-methyl-quinoline; [0304] A mixture of 4-bromo-3-methylaniline (20 g, 107.5 mmol), ferric sulfate (6.6 g, 43.4 mmol), glycerol (40.8 g, 440 mmol), nitrobenzene (8.12 g, 66 mmol), and concentrated EPO <DP n="81"/>sulfuric acid (23 ml) was heated gently. After the first vigorous reaction, the mixture was boiled for 3h and then evaporated to remove the excess nitrobenzene. The solution was added a saturated aqueous solution of sodium bicarbonate until pH=7-8, then the solution was filtered and extracted with dichloromethane. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The solid was purified by flash column chromatography to give a yellow solid, which was further washed with petroleum ether to give 7.5 g of 6-bromo-7-methyl-quinoline (31percent yield): 1H NMR (CDCl3): 2.60 (s, 3H), 7.36 (m, IH), 7.96 (s, IH), 8.04 (m, 2H), 8.89 (m, IH).
References: [1] Patent: WO2008/51808, 2008, A2, . Location in patent: Page/Page column 79-80.
  • 18
  • [ 703-91-3 ]
  • [ 56-81-5 ]
  • [ 1239460-75-3 ]
YieldReaction ConditionsOperation in experiment
48%
Stage #1: at 120℃; for 4 h;
Stage #2: With water; sodium hydroxide In ethanol; ethyl acetate; nitrobenzene at 20℃;
To a mixture of 5-bromo-2-(trifluoromethyl)aniline (3.0g, 12.6mmol), glycerol (4.64g, 50.0mmol), and ferrous sulfate (0.56 g, 2.0mmol) was added cone, sulfuric acid (2.2mL) dropwise. The reaction mixture was heated at 120 0C for 4hr. After cooled to RT, the reaction was diluted with ethyl acetate (15OmL), and 2N aq. NaOH was introduced to adjust pH about 13. The organic layer was separated and washed with brine and dried over Na2SO4 and evaporated to give the crude product, which was purified with flash column chromatography to give 5-bromo- 8-(trifluoromethyl)quinoline (1.2g, 48percent).
References: [1] Patent: WO2010/91310, 2010, A1, . Location in patent: Page/Page column 101.
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5521 - 5527.
 

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