Hisama Masayoshi, Matsuda Sanae, Arai Junichi, Masui Katsunobu, Yamamura Haruo
Central Research Center Research & Development Division, Toyo Beauty Co., Ltd.
J Oleo Sci. 2015;64(9):1033-41. doi: 10.5650/jos.ess15047.
A novel amphiphilic hydroquinone derivative having a C18 alkyl chain phosphate attached to the hydroquinone (HQ) moiety was chemically synthesized. The thermal stability, distribution between organic and aqueous phases, and in vitro skin permeability were evaluated. This HQ derivative was identified as disodium p-phenylene diisostearyl diphosphate (HQ-2P2IS) by UV, infrared, mass, and nuclear magnetic resonance spectroscopies. Product HQ-2P2IS was obtained in good yield (56%), and it exhibited satisfactory stability in neutral solution, comparable to that of HQ. Its skin permeability was also higher than that of HQ. HQ-2P2IS is susceptible to enzymatic hydrolysis by tissue phosphatase, which releases HQ in the skin tissues. Thus, these characteristics indicate that the novel hydroquinone derivative presented herein, i.e., HQ-2P2IS, may serve as an effective pro-hydroquinone for skin care applications.
合成了一种新型两亲性对苯二酚衍生物，该衍生物在对苯二酚（HQ）部分连接有C18烷基链磷酸酯。评估了其热稳定性、在有机相和水相之间的分配以及体外皮肤渗透性。通过紫外、红外、质谱和核磁共振光谱法将该HQ衍生物鉴定为对亚苯基二异硬脂基二磷酸二钠（HQ-2P2IS）。产物HQ-2P2IS的产率良好（56%），并且在中性溶液中表现出令人满意的稳定性，与HQ相当。其皮肤渗透性也高于HQ。HQ-2P2IS易受组织磷酸酶的酶促水解作用，在皮肤组织中释放出HQ。因此，这些特性表明本文介绍的新型对苯二酚衍生物，即HQ-2P2IS，可作为皮肤护理应用中的一种有效的前体对苯二酚。
