Retinoic acid
Metabolite of vitamin A / From Wikipedia, the free encyclopedia
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Retinoic acid (used simplified here for all-trans-retinoic acid) is a metabolite of vitamin A1 (all-trans-retinol) that mediates the functions of vitamin A1 required for growth and development. All-trans-retinoic acid is required in chordate animals, which includes all higher animals from fish to humans. During early embryonic development, all-trans-retinoic acid generated in a specific region of the embryo helps determine position along the embryonic anterior/posterior axis by serving as an intercellular signaling molecule that guides development of the posterior portion of the embryo.[2] It acts through Hox genes, which ultimately control anterior/posterior patterning in early developmental stages.[3]
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IUPAC name
Retinoic acid | |
Systematic IUPAC name
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid | |
Other names
vitamin A acid; RA | |
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3D model (JSmol) |
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PubChem CID |
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Properties | |
C20H28O2 | |
Molar mass | 300.43512 g/mol |
Appearance | yellow to light orange crystalline powder with a characteristic of a floral scent[1] |
Melting point | 180 to 182 °C (356 to 360 °F; 453 to 455 K) crystals from ethanol[1] |
nearly insoluble | |
Solubility in fat | soluble |
Related compounds | |
Related compounds |
retinol; retinal; beta-carotene |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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All-trans-retinoic acid (ATRA) is the major occurring retinoic acid, while isomers like 13-cis- and 9-cis-retinoic acid are also present in much lower levels.[4]
The key role of all-trans-retinoic acid in embryonic development mediates the high teratogenicity of retinoid pharmaceuticals, such as isotretinoin (13-cis-retinoic acid) used for treatment of cancer and acne. Oral megadoses of preformed vitamin A (retinyl palmitate), and all-trans-retinoic acid itself, also have teratogenic potential by this same mechanism.