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Chemical Structure| 68-26-8 Chemical Structure| 68-26-8
Chemical Structure| 68-26-8

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Vitamin A is an effective antioxidant that displays lipoperoxy radical scavenging activity and fluorescent properties. It's a ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR).

Synonyms: Retinol; all-trans Retinol; Vafol

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Product Details of Vitamin A

CAS No. :68-26-8
Formula : C20H30O
M.W : 286.45
SMILES Code : OC/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C
Synonyms :
Retinol; all-trans Retinol; Vafol
MDL No. :MFCD00001552

Safety of Vitamin A

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H317-H319-H360-H413
Precautionary Statements:P201-P273-P280-P302+P352-P305+P351+P338-P308+P313

Application In Synthesis of Vitamin A

* 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 [ 68-26-8 ]

[ 68-26-8 ] Synthesis Path-Downstream   1~9

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  • [ 79-81-2 ]
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  • [ 68-26-8 ]
  • [ 112-67-4 ]
  • [ 79-81-2 ]
YieldReaction ConditionsOperation in experiment
99% In toluene; at 35℃; for 1.0h; 900 g of vitamin A and 4 L of toluene were added to the reactor, and 860 g of palmitoyl chloride was added dropwise with stirring to control the temperature at 35 C. After the dropwise addition, the reaction was carried out at 35 C for 1h. After the reaction, wash with water to remove light components,1650 g of vitamin A palmitate solid was obtained,The content is 97% and the yield is 99%.
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  • [ 68-26-8 ]
  • [ 472-86-6 ]
  • 6
  • [ 127-47-9 ]
  • [ 57-10-3 ]
  • [ 79-81-2 ]
  • [ 68-26-8 ]
YieldReaction ConditionsOperation in experiment
78% With Novozyme 435 (from Candida antarctica immobilized on acrylic resin); Amberlyst A-21; In toluene; at 20℃; for 15.0h;Enzymatic reaction;Product distribution / selectivity; 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 89.2% conversion to retinyl palmitate with 9.1% retinyl acetate and 1.7% 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 2×20 mL with a 1:1 mixture of 10% 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 (78%) of a yellow oil. Analysis of this product indicated 91.2% retinyl palmitate (HPLC area percent), 0.4 wt % palmitic acid, and 0.2% retinol. HPLC (4.6×150 mm Zorbax SB-C8 column [Agilent], 3.5mu thickness, methanol eluent, detection at 350 nm): tR 5.52 min (retinyl palmitate); tR 2.32 min (retinyl acetate); tR 2.08 min (retinol).
  • 7
  • [ 68-26-8 ]
  • [ 472-86-6 ]
  • [ 116-31-4 ]
  • 8
  • [ 623-65-4 ]
  • [ 68-26-8 ]
  • [ 79-81-2 ]
YieldReaction ConditionsOperation in experiment
97.62% With aluminum oxide; In Petroleum ether; at 40℃; for 2.0h; (59.5 g, 0.12 mol) of palmitic anhydride was charged to a solution of (28.6 g, 0.1 mol) of vitamin A alcohol and 240 g of petroleum ether, heated slowly to 40C in a water bath, and 4.29 g of activated 200 mesh of basic alumina was added. Insulation reaction 2 hours, liquid tracking detection of vitamin A residual alcohol ? 0.3% to stop the antiShould, filter out the basic alumina, -12 cold treatment, filter residue, the filtrate for dissolution, obtainedLight yellow oily liquid product (51.2 g, 97.62% molar yield). The HPLC analysis of the product was in accordance with the standard. The product was analyzed by USP28. The biological titer was 1.781 million IU / g and the content was 98.3%.
  • 9
  • [ 112-39-0 ]
  • [ 68-26-8 ]
  • [ 79-81-2 ]
YieldReaction ConditionsOperation in experiment
94% at 60℃; under 0.750075 Torr; for 3.0h;Large scale; 3.28 kg of vitamin A acetate and 16.5 g of potassium methoxide were added to 33 L of methanol under nitrogen protection, and the reaction was carried out at 30 C for about 3hour;After completion of the reaction, it was concentrated to dryness under reduced pressure at 40 C to give a yellow oil as a vitamin A alcohol.The obtained vitamin A alcohol was mixed with 2.80 kg of methyl palmitate.The mixture was heated to 60 C and then the pressure was reduced to about 100 Pa for about 3 hours.The reaction was terminated by nitrogen gas, and 20 L of n-hexane and 165 g of activated carbon were added.After decolorizing for 30 minutes, the silica gel was filtered, and the filtrate was concentrated to dryness under reduced pressure.A pale yellow oil of 4.93 kg was obtained with a yield of 94%.The obtained oil was analyzed according to the method of the United States Pharmacopoeia USP28, and the result showed that the purity of vitamin A palmitate was 1.77 million IU/g.
 

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