oleyl adapalenate
{{Chembox
| Name = Oleyl adapalenate
| ImageFile = Oleyl adapalenate.svg
| IUPACName = (9Z)-Octadecen-1-yl 6-(4-methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-2-naphthalenecarboxylate
| Section1 = {{Chembox Identifiers
| CASNo = 2797026-98-1
| PubChem = 172866691
| UNII = GRS4SNP9WC
| StdInChI=1S/C46H62O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-25-49-45(47)42-22-21-38-29-39(19-20-40(38)30-42)41-23-24-44(48-2)43(31-41)46-32-35-26-36(33-46)28-37(27-35)34-46/h10-11,19-24,29-31,35-37H,3-9,12-18,25-28,32-34H2,1-2H3/b11-10-
| StdInChIKey = PAMUYVOXXQOZMG-KHPPLWFESA-N
| SMILES = CCCCCCCCC=CCCCCCCCCOC(=O)c6ccc5cc(c4ccc(OC)c(C23CC1CC(CC(C1)C2)C3)c4)ccc5c6
}}
| Section2 = {{Chembox Properties
| C=46|H=62|O=3
}}
}}
Oleyl adapalenate, sold under the brand name Adapinoid, is a lipophilic derivative of adapalene, and is a third-generation synthetic retinoid. It is primarily utilized in topical cosmetic formulations for the treatment of skin conditions associated with photoaging, rhytides (wrinkles), and acne induced post-inflammatory erythema, post-inflammatory hyperpigmentation, and scarring. Oleyl adapalenate differentiates itself from earlier retinoids by offering improved skin tolerability, reduced irritation, and enhanced stability.{{Cite journal |last1=Nguyen |first1=Nhi |last2=Afzal |first2=Nasima |last3=Min |first3=Mildred |last4=Ahmad |first4=Nabeel |last5=Afzal |first5=Laila |last6=Burney |first6=Waqas |last7=Chambers |first7=Cindy J. |last8=Sivamani |first8=Raja K. |date=2024-12-01 |title=A Prospective, Double-Blinded, Randomized Head-to-Head Clinical Trial of Topical Adapinoid (Oleyl Adapalenate) Versus Retinol |journal=Skin Health and Disease |language=en |volume=4 |issue=6 |pages=e469 |doi=10.1002/ski2.469 |issn=2690-442X |pmc=11608876 |pmid=39624736}}
Structure
The structure of oleyl adapalenate is similar to that of adapalene, but with oleyl alcohol covalently bound via an ester bond to the free carboxylate group of adapalene.{{Cite patent|number=US12133907B2|title=Lipophilic third generation retinoid|gdate=2024-11-05|invent1=Winn|inventor1-first=Daniel|url=https://patents.google.com/patent/US12133907B2/en}} The lipophillic character of oleyl adapalenate allows it to be soluble in skincare oils and emollients, whereas adapalene, being neither lipophilic nor hydrophilic, has low solubility in solvents and is limited in how it can be compounded and delivered in topical drugs.{{Cite journal |last1=Rusu |first1=Aura |last2=Tanase |first2=Corneliu |last3=Pascu |first3=Georgiana-Andreea |last4=Todoran |first4=Nicoleta |date=2020-08-28 |title=Recent Advances Regarding the Therapeutic Potential of Adapalene |journal=Pharmaceuticals |language=en |volume=13 |issue=9 |pages=217 |doi=10.3390/ph13090217 |doi-access=free |issn=1424-8247 |pmc=7558148 |pmid=32872149}}
Uses
Because oleyl adapalenate does not have the inherent oxidative instability of Vitamin A, it may be employed as a substitute for retinol and retinaldehyde in consumer skincare regimens for anti-aging, skin rejuvenation, and anti-acne.{{Cite journal |last1=Pradhan |first1=Sneha Jateen |last2=Kuchekar |first2=Ashwin |last3=Gawade |first3=Ashwini |last4=Kore |first4=Sushil |date=2024 |title=Retinoids—A unique ingredient for skin rejuvenation employing novel drug delivery systems |url=https://japsonline.com/abstract.php?article_id=4265&sts=2 |journal=Journal of Applied Pharmaceutical Science |language=en |doi=10.7324/JAPS.2024.168608 |issn=2231-3354|doi-access=free }}{{Cite journal |last1=Zasada |first1=Malwina |last2=Budzisz |first2=Elżbieta |date=2019 |title=Retinoids: active molecules influencing skin structure formation in cosmetic and dermatological treatments |journal=Advances in Dermatology and Allergology |volume=36 |issue=4 |pages=392–397 |doi=10.5114/ada.2019.87443 |issn=1642-395X |pmc=6791161 |pmid=31616211}} Furthermore, country regulatory authorities such as the European Union are limiting the use Vitamin A in cosmetics due to safety concerns, and these restrictions are not applicable to oleyl adapalenate{{Cite web |date=2024-04-04 |title=Everything you need to know about the EU retinol ban |url=https://www.independent.co.uk/extras/indybest/fashion-beauty/beauty/eu-retinol-ban-b2511235.html |access-date=2025-03-14 |website=The Independent |language=en}}