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Chemical Structure| 57-88-5 Chemical Structure| 57-88-5
Chemical Structure| 57-88-5

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Cholesterol is the major sterol in mammals, and its importance in fundamental cellular processes is becoming more appreciated.

Synonyms: Cholesterin; NSC 8798; HSDB 7106

4.5 *For Research Use Only !

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Product Citations

Product Citations

Federica Carnamucio ; Victoria A. Garcia ; Fatemah S. Sunbul ; Ottavia Giuffrè ; Sandro R. P. da Rocha ;

Abstract: Osteosarcoma (OS) is the most prevalent primary bone malignancy and ranks as the third most common cancer in children, almost exclusively metastasizing to the lungs. Upon initial OS diagnosis, approximately 20% of patients are also diagnosed with clinically detectable lung metastases (OSLM). Systemic gemcitabine (GMT) is the second line therapy for OSLM, but it has limited efficacy due to poor lung distribution. Orally inhaled GMT is in clinical studies and has been shown to upregulate the apoptotic Fas receptor (FasR) expression in OS cells in the lungs, but fails to eradicate lung mets due to its poor lung disposition. Traditional liposomal GMT formulations may offer improved lung safety and retention, but struggle with storage stability and drug loading. We have developed a new GMT unilmellar liposomal formulation that has enhanced GMT loading, high storage stability (<5% GMT leakage in six months storage at 2-8 °C), and is also suitable for oral inhalation. Importantly, we have subsequently developed a strategy for reproducible preparation of the formulation using as single step, GMP-ready, continuous microfluid platform. We also evaluated the efficacy of the formulation in promoting cell death and to rescuing FasR expression in OSLM tumor cells, and we demonstrated that GMT activity is preserved. We also demonstrated that our formulation is well tolerated at repeated doses upon local delivery to the lungs in healthy mice, since no change in body weight or health status have been observed.

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Product Details of Cholesterol

CAS No. :57-88-5
Formula : C27H46O
M.W : 386.65
SMILES Code : CC(C)CCC[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C
Synonyms :
Cholesterin; NSC 8798; HSDB 7106
MDL No. :MFCD00003646
InChI Key :HVYWMOMLDIMFJA-DPAQBDIFSA-N
Pubchem ID :5997

Safety of Cholesterol

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Cholesterol

* 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.

  • Downstream synthetic route of [ 57-88-5 ]

[ 57-88-5 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 422-64-0 ]
  • [ 57-88-5 ]
  • [ 66997-77-1 ]
  • 2
  • [ 57-88-5 ]
  • [ 150374-99-5 ]
  • 5-cholesten-3β-yl (p-pivaloyloxybenzenesulfonate) [ No CAS ]
  • 3
  • [ 128-37-0 ]
  • [ 57-88-5 ]
  • [ 83883-26-5 ]
  • [ 206053-52-3 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; In pyridine; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; chloroform; N,N-dimethyl-formamide; A Cholesteryl 4-(6-acryloyloxyhexyloxy)benzoate STR13 2.92 g (0.01 mole) 4-(6-acryloyloxyhexyloxy)benzoic acid is dissolved in 10 mL CHCl3 and two drops of N,N-dimethylformamide and 30 mg of 2,6-di-tert-butyl-p-cresol were added. Next, 15 mL thionyl chloride was added dropwise to the solution which was stirred at 70° C. until no more gas was given off (approx. 1-2 hours). Then, the CHCl3 and excess thionyl chloride were distilled off under vacuum. The residue is 4-(6-acryloyloxyhexyloxy)benzoyl chloride. The acid chloride was dissolved in 30 mL absolute ether and at 0 to 5° C. added dropwise to 3.86 g (0.01 mole) cholesterol in 10 mL pyridine. It was then stirred for 17 hours at 50° C. For workup, the solution was poured into 200 to 300 mL ice water and acidified with conc. HCl. The product precipitated as a white precipitate. The precipitate was filtered off, washed with saturated NaHCO3 solution, and then with H2 O. It was then recrystallized twice from 100-mL portions of ethanol. After drying, 4.5 g (69percent) white crystals 27 are obtained. Characterization 1 H NMR (CHCl3): 0.65 (s, 3H); 0.8 to 2.1 (m, 46 H); 2.45 (m, 2H); 3.88 (t, 2H); 4.15 (t, 2H); 4.821 (m, 1H); 5.40 (m, 1H); 5.80 (dd, 1H); 6.10 (dd, 1H); 6.38 (dd, 1H); 6.85 (d, 2H); 7.95 (d, 2H) ppm 13 C NMR (CDCl3): 11.82; 18.68; 19.34; 21.01; 22.52; 22.78; 23.80; 24.24; 25.66; 27.95; 28.19; 28.49; 28.96; 31.85; 35.75; 36.15; 36.60; 37.01; 38.25; 39.47; 39.70; 42.47; 50.00; 56.10; 56.64; 64.39; 67.87; 74.12; 113.89; 122.59; 123.05; 128.52; 130.44; 131.46; 139.71; 162.66; 165.69; 166.20 ppm IR (KBr): 2943; 2866; 1717; 1634; 1605; 1510; 1273; 1250; 1198; 1167; 1115; 1007; 772 cm-1
  • 4
  • [ 57-88-5 ]
  • [ 7732-18-5 ]
  • [ 60076-09-7 ]
  • m-iodobenzyl cholesteryl ether [ No CAS ]
YieldReaction ConditionsOperation in experiment
With NaH; In 1,2-dimethoxyethane; benzene cyclohexane; Cholesterol (568 mg, 1.98 mmol), anhydrous dimethoxyethane (8.0 ml), and NaH (140 mg, 15.8 mmol) were combined in a flame-dried, nitrogen flushed round-bottom flask which was fitted with a reflux condenser. The resulting mixture was stirred for 5 minutes at room temperature before m-iodobenzyl chloride (550 mg, 1.98 mmol) was slowly added with continued stirring. The reaction mixture was refluxed for 6 hours. After the reaction mixture had cooled to room temperature, H2 O (20 ml) was added. The organic layer was extracted with ether (20 ml, 3X). The ether extracts were dried over MgSO4 and the solvent was removed under reduced pressure. The resulting solid residue was dissolved in benzene-hexane (3:7 and purified on a chormatography column of silica gel (53 g silica; benzene-hexane 3:7) to yield m-iodobenzyl cholesteryl ether as a white solid. The m-iodobenzyl cholesteryl ether was recrystallized from acetone (472 mg, 40%, mp 95-96 C.).
  • 5
  • γ-benzyl glutamate [ No CAS ]
  • fluorenylmethyloxycarbonyl chloride [ No CAS ]
  • [ 57-88-5 ]
  • [ 123639-61-2 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In 1,4-dioxane; water; EXAMPLE 106 N-alpha-(FMOC)-glutamic acid -gamma-benzyl ester (106) To a solution of gamma-benzyl glutamate (10 mmol) in 50 ml dioxane and 50 ml water is added triethylamine (25 mmol), followed by a solution of fluorenylmethyl chloroformate (11 mmol) in 50 ml dioxane. The mixture is vigorously stirred until the starting material is consumed. The solution is acidified to pH 2 with concentrated HCl, extracted with ethyl acetate (2 X 250 ml), washed with brine, dried with MgSO4 and evaporated. The product is used without purification.
  • 6
  • [ 57-88-5 ]
  • [ 83883-26-5 ]
  • [ 206053-52-3 ]
  • 7
  • [ 57-88-5 ]
  • [ 1397-89-3 ]
  • amphotericin B-cholesterol complex [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dimethyl sulfoxide; at 20 - 80℃; for 1.5h;Sealed tube; To make a pre-complexed aggregate of AmB and cholesterol (Choi) for the studies herein, Choi was first prepared as a 4 mg/mL in CHCh stock solution. 965 mu. of this solution was added to a 7 mL glass vial and the solvent removed under a gentle stream of nitrogen gas. 1 mL of a DMSO solution of 2 mM AmB was then added to the solid Choi to make a 10 mM final Choi concentration, a 1 :5 mole ratio Choi: AmB suspension. A small stir bar was added to this suspension, and the vial was capped and heated to 80 C for one hour in an aluminum heating block to allow Choi to fully dissolve, stirring at 300 rpm. The resulting AmB:Chol solution was then allowed to cool to room temperature. This solution was left to complex at room temperature for another 30 minutes before dividing into 100 mug aliquots and lyophilized overnight.
 

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