Back حمض الرتينويك Arabic رتینوئیک اسید AZB Retinoidna kiselina BS Àcid retinoic Catalan Retinsäuren German Ácido retinoico Spanish Azido erretinoiko Basque رتینوئیک اسید Persian Acide rétinoïque French Ácido retinoico Galician

Retinoic acid

For all-trans-retinoic acid as a drug, see Tretinoin. For 9-cis-retinoic acid as a drug, see Alitretinoin. For 13-cis-retinoic acid as a drug, see Isotretinoin.

All-trans-retinoic acid
Skeletal formula of retinoic acid
Ball-and-stick model of the retinoic acid molecule
Names
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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+
    Key: SHGAZHPCJJPHSC-YCNIQYBTSA-N
  • CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C
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
 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]

  1. ^ a b Merck Index, 13th Edition, 8251.
  2. ^ a b Hall JA, Grainger JR, Spencer SP, Belkaid Y (July 2011). "The role of retinoic acid in tolerance and immunity". Immunity. 35 (1): 13–22. doi:10.1016/j.immuni.2011.07.002. PMC 3418663. PMID 21777796.
  3. ^ Duester G (September 2008). "Retinoic acid synthesis and signaling during early organogenesis". Cell. 134 (6): 921–931. doi:10.1016/j.cell.2008.09.002. PMC 2632951. PMID 18805086.
  4. ^ Holland LZ (May 2007). "Developmental biology: a chordate with a difference". Nature. 447 (7141): 153–155. Bibcode:2007Natur.447..153H. doi:10.1038/447153a. PMID 17495912. S2CID 5549210.
  5. ^ Topping T, Griswold MD (2022-04-28). "Global Deletion of ALDH1A1 and ALDH1A2 Genes Does Not Affect Viability but Blocks Spermatogenesis". Frontiers in Endocrinology. 13: 871225. doi:10.3389/fendo.2022.871225. PMC 9097449. PMID 35574006.
  6. ^ Esposito M, Amory JK, Kang Y (September 2024). "The pathogenic role of retinoid nuclear receptor signaling in cancer and metabolic syndromes". The Journal of Experimental Medicine. 221 (9). doi:10.1084/jem.20240519. PMID 39133222.
  7. ^ Rühl R, Krezel W, de Lera AR (December 2018). "9-Cis-13,14-dihydroretinoic acid, a new endogenous mammalian ligand of retinoid X receptor and the active ligand of a potential new vitamin A category: vitamin A5". Nutrition Reviews. 76 (12): 929–941. doi:10.1093/nutrit/nuy057. PMID 30358857.
  8. ^ "PRAC Seeks New Pregnancy Prevention Measures For Retinoids". Medscape. Retrieved 2024-08-15.
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