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| ALL-TRANS-RETINAL Basic information |
| Product Name: | ALL-TRANS-RETINAL | | Synonyms: | 2,4,6,8-Nonatetraenal, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-;2,4,6,8-Nonatetraenal, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)-;all-E-Retinal;all-trans-retina;All-trans-Retinaldehyde;alpha-Retinene;Axerophthal;E-Retinal | | CAS: | 116-31-4 | | MF: | C20H28O | | MW: | 284.44 | | EINECS: | 204-135-8 | | Product Categories: | Vitamins;Aldehydes;Antitumor Agents;Building Blocks;C13-C60;Cancer Research;Carbonyl Compounds;Chemical Synthesis;Cofactor;Gene Regulation;Isoprenoid;Metabolic Pathways;Metabolites and Cofactors on the Metabolic Pathways Chart;Metabolomics;Intermediates & Fine Chemicals;Pharmaceuticals;Retinoids;Nutrition Research;Organic Building Blocks;Vitamin A | | Mol File: | 116-31-4.mol |
| ALL-TRANS-RETINAL Chemical Properties |
| Melting point | 61-63°C | | Boiling point | 366.92°C (rough estimate) | | density | 1.0083 (rough estimate) | | refractive index | 1.4500 (estimate) | | storage temp. | -20°C | | solubility | Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) | | form | powder | | color | yellow | | Water Solubility | <70mg/L(25 ºC) | | Stability: | Hygroscopic, Light Sensitive, Temperature Sensitive | | CAS DataBase Reference | 116-31-4(CAS DataBase Reference) | | EPA Substance Registry System | Retinal (116-31-4) |
| Hazard Codes | Xn | | Risk Statements | 22-38 | | Safety Statements | 22-36/37 | | WGK Germany | 3 | | RTECS | VH6407000 | | HS Code | 29122990 |
| ALL-TRANS-RETINAL Usage And Synthesis |
| Chemical Properties | Yellow Powder | | Uses | Corotenoid component of the visual pigments. All-trans retinal is converted to retinoic acid in vivo by the action of retinal dehydrogenase. | | Uses | All trans-Retinal has been used:- in optogenetic experiments
- in electrophysiological experiment
- to study the effect of AKR1B10 (aldo-keto reductase (AKR) superfamily member) on the conversion of retinal to retinol in the airway epithelium
- in decidual transformation of human endometrial stromal cells
| | Uses | retinaldehyde is a mild retinoid credited with increasing epidermal thickness without producing erythema. | | Definition | ChEBI: A retinal in which all four exocyclic double bonds have E- (trans-) geometry. | | Synthesis Reference(s) | Tetrahedron Letters, 29, p. 419, 1988 DOI: 10.1016/S0040-4039(00)80111-2 | | General Description | All trans-Retinal is one of the major derivatives of vitamin A group. A variety of food serves as a source of vitamin A. It is predominant in liver and among the brightly colored vegetables. | | Biological Activity | all-trans retinal, also known as vitamin a aldehyde or retinaldehyde, is one of the many forms of vitamin a and also the oxidation product of all-trans retinol [1]. all-trans retinal are associated with one of the two isoforms of cellular retinol-binding proteins (crbp-i and crbp-ii) with kd values of 50 and 90 nm, respectively [1].crbp-i and crbp-ii were the first intracellular retinoid-binding proteins. both proteins display a similar binding affinity towards retinal. they play important roles in retinoid biology and regulation of the metabolism of retinol and retinal. crbp-i is used to regulate vitamin a storage and synthesis of retinoic acid. and crbp-ii has a role in the initial processing of retinol from food [1].all-trans retinal is one form of vitamin a. all-trans retinal, the initial substrate of retinoid cycle, is a chemically reactive aldehyde that can form toxic conjugates with proteins and lipids, leading to degeneration of the retina [2]. | | Biochem/physiol Actions | All-trans retinal is converted to retinoic acid in vivo by the action of retinal dehydrogenase. Retinoic acid is a ligand for both the retinoic acid receptor (RAR) and the retinoid X receptor (RXR) that act as transcription factors to regulate the growth and differentiation of normal and malignant cells. Retinal isomers are also chromophores that bind to opsins, a family of G-protein-linked transmembrane proteins, to form photosensitive receptors in visual and nonvisual systems. All-trans retinal is a potent photosensitizer. | | Purification Methods | The aldehyde is separated from retinol by column chromatography on water-deactivated alumina. Elute with 1-2% acetone in hexane, or on TLC plates of silica gel G and using the same eluting solvent. It crystallises from pet ether or n-hexane as yellow-orange crystals, and the UV in hexane has max at 373nm (A1cm 1% 1,548) and 368nm ( 48,000). It is an irritant and is light sensitive. Store it in sealed ampoules under N2. The semicarbazone forms yellow crystals from CHCl3/Et2O or EtOH, m 199-201o(dec). The 9-cis-isomer [514-85-2] and the 13-cis-isomer [472-86-6] [max at 375nm ( 1,250) in EtOH] are also available commercially. [Beilstein 7 III 1742.] | | references | [1]. noy n. retinoid-binding proteins: mediators of retinoid action. biochem j. 2000 jun 15;348 pt 3:481-95.[2]. kiser pd, golczak m, maeda a, et al. key enzymes of the retinoid (visual) cycle in vertebrate retina. biochim biophys acta. 2012 jan;1821(1):137-51. |
| ALL-TRANS-RETINAL Preparation Products And Raw materials |
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