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Retinol

Base Information Edit
  • Chemical Name:Retinol
  • CAS No.:68-26-8
  • Deprecated CAS:13123-33-6,17104-91-5,5979-23-7,1341-18-0,1406-67-3,53637-36-8,5979-23-7
  • Molecular Formula:C20H30O
  • Molecular Weight:286.458
  • Hs Code.:29362100
  • European Community (EC) Number:200-683-7,234-328-2
  • NSC Number:758150,122759
  • UNII:G2SH0XKK91
  • DSSTox Substance ID:DTXSID3023556
  • Nikkaji Number:J490.500H,J540.270K,J641.040E,J641.434F,J641.435D,J1.417F
  • Wikipedia:Retinol,Vitamin_A
  • Wikidata:Q424976
  • NCI Thesaurus Code:C68302
  • RXCUI:11246
  • Pharos Ligand ID:LKB2KDK4XY9M
  • Metabolomics Workbench ID:29025
  • ChEMBL ID:CHEMBL986
  • Mol file:68-26-8.mol
Retinol

Synonyms:11-cis-Retinol;3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, (all-E)-Isomer;All Trans Retinol;All-Trans-Retinol;Aquasol A;Retinol;Vitamin A;Vitamin A1

Suppliers and Price of Retinol
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • Usbiological
  • Vitamin A
  • 48Tests
  • $ 675.00
  • Usbiological
  • Vitamin A
  • 48Tests
  • $ 675.00
  • Usbiological
  • Vitamin A
  • 48Tests
  • $ 639.00
  • Usbiological
  • all-trans-Retinol
  • 50mg
  • $ 319.00
  • TRC
  • all-trans-Retinol
  • 25mg
  • $ 40.00
  • TRC
  • all-trans-Retinol
  • 250mg
  • $ 100.00
  • TRC
  • all-trans-Retinol
  • 100mg
  • $ 55.00
  • Sigma-Aldrich
  • Retinol solution 100 μg/mL ± 25% (Refer to COA) (Ethanol with 0.1% (w/v) BHT), ampule of 1?mL, reference material, Cerilliant?
  • 1 mL
  • $ 108.00
  • Sigma-Aldrich
  • Retinol solution 100 μg/mL ± 25% (Refer to COA) (Ethanol with 0.1% (w/v) BHT), ampule of 1 mL, certified reference material
  • 011-1ml
  • $ 105.00
  • Sigma-Aldrich
  • Retinol synthetic, ≥95% (HPLC), crystalline
  • 25mg
  • $ 43.70
Total 207 raw suppliers
Chemical Property of Retinol Edit
Chemical Property:
  • Appearance/Colour:yellow to orange crystalline solid 
  • Vapor Pressure:7.35E-09mmHg at 25°C 
  • Melting Point:63.5 ºC 
  • Refractive Index:1.641  
  • Boiling Point:421.2 ºC at 760 mmHg 
  • PKA:14.09±0.10(Predicted) 
  • Flash Point:147.3 ºC 
  • PSA:20.23000 
  • Density:0.954 g/cm3 
  • LogP:5.51030 
  • Storage Temp.:2-8°C 
  • Sensitive.:Moisture & Light Sensitive 
  • Solubility.:Chloroform (Slightly), Methanol (Slightly) 
  • Water Solubility.:Practically insoluble inwaterorglycerol; soluble in absolute alcohol,methanol,℃hloroform, ether, fats and oils. 
  • XLogP3:5.7
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:1
  • Rotatable Bond Count:5
  • Exact Mass:286.229665576
  • Heavy Atom Count:21
  • Complexity:496
Purity/Quality:

99.3% *data from raw suppliers

Vitamin A *data from reagent suppliers

Safty Information:
  • Pictogram(s): HarmfulXn,DangerousN,Flammable
  • Hazard Codes:Xn,N,F,T 
  • Statements: 22-38-67-65-62-51/53-48/20-11-43-61-63-36/38 
  • Safety Statements: 36/37-61-62-45-53-16-33-29-9-36/37/39-26 
MSDS Files:

SDS file from LookChem

Useful:
  • Chemical Classes:Biological Agents -> Vitamins and Derivatives
  • Drug Classes:Vitamins (Vitamin A)
  • Canonical SMILES:CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CCO)C)C
  • Isomeric SMILES:CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/CO)/C)/C
  • Recent ClinicalTrials:Quintuple Method for Treatment of Multiple Refractory Colorectal Liver Metastases
  • Recent EU Clinical Trials:Vitamin D and atopic allergy
  • Recent NIPH Clinical Trials:HELIOS-B: A Study to Evaluate Vutrisiran in Patients with Transthyretin Amyloidosis with Cardiomyopathy
  • General Description Vitamin A, also known as retinol and other synonyms listed, is a fat-soluble vitamin essential for biological functions such as vision, cell differentiation, growth, and reproduction. Structurally, its activity is highly dependent on the presence of methyl groups on its sidechain, as demonstrated by studies showing that desmethyl homologues (e.g., 9-, 13-, or 9,13-desmethyl variants) exhibit significantly reduced or no growth-promoting activity compared to the all-trans form. Retinoids, derived from precursors like β-carotene via chemical reactions such as cross metathesis, are critical in synthesizing biologically active vitamin A analogues for research and therapeutic applications. The integrity of the all-trans configuration and methyl group positioning is crucial for its biological efficacy.
Technology Process of Retinol

There total 178 articles about Retinol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
(9Ξ)-O-acetyl-retinol; With sodium hydroxide; In ethanol; water; at 40 ℃; for 0.5h; Inert atmosphere; Darkness;
With pyridine; In Methyl formate; at 0 ℃; for 2h; Reagent/catalyst; Catalytic behavior;
DOI:10.1039/c9dt02189b
Refernces Edit

Biosensor-Based Determination of Riboflavin in Milk Samples

10.1021/ac034876a

The study presents the development of a biosensor-based assay for the quantification of riboflavin (Rf) in milk samples using surface plasmon resonance (SPR) technology. The assay involves the indirect measurement of Rf by detecting the excess of riboflavin binding protein (RBP) that remains free after complexation with Rf molecules originally present in the sample. The sensor chip is modified with covalently immobilized Rf to bind the excess RBP. The method involves a chemical modification to introduce a reactive ester group on the Rf molecule for immobilization on the chip surface. Calibration solutions are prepared by mixing Rf standard solutions with an optimized concentration of RBP, and the Rf content in milk samples is measured by comparing the response against the calibration. The results are comparable to those obtained from an official HPLC-fluorescence procedure, with a limit of quantification determined to be 234 μg/L and a limit of detection to 70 μg/L. The study demonstrates the potential of SPR-based biosensors as a competitive alternative to traditional analytical techniques for the determination of riboflavin in food samples.

Cross metathesis of β-carotene with electron-deficient dienes. A direct route to retinoids

10.1016/j.tetlet.2009.06.032

The study focuses on the cross metathesis (CM) reactions of β-carotene with electron-deficient dienes, specifically using the Hoveyda second generation catalyst, to synthesize retinoids, which are compounds related to vitamin A and play a crucial role in various biological processes such as vision, reproduction, cell differentiation, and growth. The primary chemicals used in the study include β-carotene, ethyl (2E,4E/Z)-3-methylhexa-2,4-dienoate, and the Hoveyda II catalyst. The purpose of these chemicals is to undergo CM reactions, which are a type of olefin metathesis reaction that forms new carbon-carbon bonds under mild conditions, to produce retinoids like ethyl all-trans-retinoate. The study explores the regioselectivity and diastereoselectivity of these reactions, aiming to develop an effective and fast method for the preparation of retinoids for biological and structural studies.

Vitamin A analogues. V. Synthesis of 9-, 13-, and 9,13- desmethyl homologues of vitamin A.

10.1016/0040-4020(66)80130-8

The research aimed to investigate the relationship between the chemical structure and biological activity of vitamin A by synthesizing 9-, 13-, and 9,13-desmethyl homologues of vitamin A acetate. The study concluded that the presence of both methyl groups on the sidechain of the all-trans system is essential for growth-promoting properties, as the all-trans-13- and all-trans-9,13-desmethyl vitamin A acetates showed no activity, while the all-trans-9-desmethyl vitamin A acetate exhibited only about 4% of the activity compared to all-trans-vitamin A acetate. The synthesis involved chemicals such as truns-ionylidene acetaldehyde, truns-(2’,6’,6’-trimethylcyclohexen-1’-yl-1’)-pentadiene 2,4- dial, phosphonates of the appropriate crotonic acid esters, and reagents like lithium aluminum hydride (LAH) or diisobutylaluminum hydride (DIBAH) for reduction steps. Biological investigations were conducted to assess the growth-promoting properties of these synthesized compounds.

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