8165. Retinoic Acid

Nomenclature

CAS number: 302-79-4
(all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; all-trans-retinoic acid; vitamin A acid; tretinoin; Aberel (Janssen-Cilag); Airol (Pierre Fabre); Avita (Bertek); Epi-Aberel (Janssen-Cilag); Eudyna (BASF); Kerlocal (Pierre Fabre); Renova (Ortho); Retin-A (Ortho); Retinova (Janssen-Cilag); Vesanoid (Roche).
C20H28O2; mol wt 300.44.
C 79.95%, H 9.39%, O 10.65%.

Description and references

Physiological metabolite of vitamin A, q.v. Effects gene expression via nuclear retinoic acid receptors (RAR); mediates cellular growth and differentiation. Prepn: D. A. van Dorp, J. R. Arens, Rec. Trav. Chim. 65, 338 (1946); C. D. Robeson et al., J. Am. Chem. Soc. 77, 4111 (1955). Single-step process: R. Marbet, DE 2061507; US 3746730 (1971, 1973 both to Hoffmann-La Roche). Crystal structure: C. H. Stam, C. H. MacGillavry, Acta Crystallogr. 16, 62 (1963). Toxicology: J. J. Kamm, J. Am. Acad. Dermatol. 6, 652 (1982). Clinical evaluation in treatment of photoaged skin: J. S. Weiss et al., J. Am. Med. Assoc. 259, 527 (1988); in promyelocytic leukemia: R. P. Warrell, Jr. et al., Leukemia 8, 929 (1994). Review of pharmacology and therapeutic potential: G. D. Goss et al., Crit. Rev. Clin. Lab. Sci. 29, 185-215 (1992). Book: The Retinoids, M. B. Sporn et al., Eds. (Raven Press, New York, 2nd ed., 1994) 679 pp.

Chemical structure

Properties

Yellow to light orange crystalline powder with characteristic floral odor. Crystals from ethanol, mp 180-182°. uv max (methanol): 351 nm (ε 45000). Sol in DMSO; slightly sol in polyethylene glycol 400, octanol, ethanol. Practically insol in water, mineral oil, glycerin. LD50 (10 day) in mice, rats (mg/kg): 790, 790 i.p.; 2200, 2000 orally (Kamm).

Derivative

9-cis-Form see Alitretinoin.

Derivative

13-cis-Form see Isotretinoin.

Derivative

α-Tocopheryl ester see Tocoretinate.

Therapeutic Category

Antiacne; adjunct in treatment of photodamaged skin; antineoplastic (hormonal).

Keywords

Antiacne; Keratolytic