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Names | |
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IUPAC name
Retinoic acid
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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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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
PubChem CID
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UNII | |
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Properties | |
C20H28O2 | |
Molar mass | 300.442 g·mol−1 |
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
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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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Retinoic acid (simplified nomenclature for all-trans-retinoic acid) is a metabolite of vitamin A1 (all-trans-retinol) that is required for embryonic development, male fertility, regulation of bone growth and immune function.[2] All-trans-retinoic acid is required for chordate animal development, 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.[3] It acts through Hox genes, which ultimately control anterior/posterior patterning in early developmental stages.[4] In adult tissues, the activity of endogenous retinoic acid appears limited to immune function.[2] and male fertility.[5] Retinoic acid administered as a drug (see tretinoin and alitretinoin) causes significant toxicity that is distinct from normal retinoid biology.[6]
All-trans-retinoic acid is the major occurring retinoic acid, while isomers like 13-cis- and 9-cis-retinoic acid are also present in much lower levels.[7]
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 acne or retinol used for skin disorders. High oral doses of preformed vitamin A (retinyl palmitate), and all-trans-retinoic acid itself, also have teratogenic potential by this same mechanism.[8]