| 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 |
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| 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 |
| Provider |
Language |
| SigmaAldrich |
English |
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| 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 |
retinaldehyde is a mild retinoid credited with increasing epidermal thickness without producing erythema. |
| 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
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| 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.
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| 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.] |
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| ALL-TRANS-RETINAL Preparation Products And Raw materials |
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China (Mainland)
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