356 JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS TABLE VI Hydrolysis of Pyridoxine-3,4-dibutyrate Sample No. Time for Hydrolysis Amount Hydrolyzed, wt. % Liver Kidney Intestine Blood Average Average Average 1 hr. 0.5 hr. 105.8 98.9 98.9 80.1 94.6 90.9 ... 74.2 95.4 106.8 104.5 81.8 98.6 98.8 101.7 78.7 106.6 108.0 92.8 70.4 ... 97.5 107.6 69.6 98.4 98.9 104.4 66.2 102.5 101.4 101.6 68.7 105.6 106.2 99.2 64.6 89.2 104.8 106.8 71.1 107.9 108.0 88.4 56.7 100.9 106.3 98.1 64.1 TABLE VII Hydrolysis of Pyridoxine-3,4-dioctanoate Sample No. Amount Hydrolyzed, wt. % Ti•ne for Hydrolysis Liver Kidney Intestine Blood Average Average Average 91.5 82.3 82.2 0 2 hr. 87.6 69.2 82.3 0 101.7 79.0 87.2 0 93.6 76.8 83.6 0 74.5 66.8 84.2 0 1 hr. 85.2 85.8 84.2 0 84.7 75.6 82.7 0 83.9 76.1 80.2 0 63.1 72.4 64.1 0 0.5 hr. 62.9 61.6 59.8 0 84.0 76.4 79.9 0 70.0 70.1 67.9 0 TABLE VIII Hydrolysis of Pyridoxine-3,4-dilaurate Sample No. Time for Hydrolysis Liver Amount Hydrolyzed, wt. % Kidney Intestine Average 2 hr. 11.1 0 0.9 7.6 0 1.0 10.1 0 0.8 9.6 0 0.9

PYRiDOXINE-3,4-DIACYLATES IN COSMETICS 357 solution. One mi. of one of the pyridoxine-3,4-diacylates solutions was added, and the flasks were shaken for 0.5, 1 or 2 hours at 37øC to hydrolyze the ester. After shaking, 3 mi. of 10g aqueous trichloro- acetic acid solution was added, and the mixture was centrifugcd. Five mi. of the supernatant was neutralized with 1.5% NaOH solution. For 1 mi. of the solution thus obtained, concentration of pyridoxine was determined by using 2,6-dibromoquinone chloroimide at 650 mt•. The results are shown in Tables VI, VII, VIII, and IX. It can be seen that the dibutyrate was rapidly hydrolyzed in the blood and TABLE IX Hydrolysis of Pyridoxine-3,4-dipalmitate Amount Hydrolyzed, wt. % Sample Time for No. Hydrolysis Liver Kidney Intestine 1 0 0 0 2 2.3 0 0 3 2 hr. 1.3 0 0 4 0.4 0 0 Average 1.0 0 0 organ homogenates. The dioctanoate was not hydrolyzed in the blood but slightly in the organ homogenates. On the other hand, dilaurate and dipalmitate were not hydrolyzed even in the liver homogenate. Derreal Therapy During the clinical test, which was designed to demonstrate efficacy against several kinds of dermatitis, such as eczema and seborrhoea, hydrophilic ointments and lotions containing 0.2% and 0.02% pyr- idoxine-3,4-dipalmitate respectively were applied topically. The re- sults showed that pyridoxine-3,4-dipalmitate was an effective treatment for skin diseases without any harmful side effects. It is also noted that this substance showed marked antidandruff and anti-itching properties, as judged from the following studies. Fourteen dermal outpatients (7) suffering from eczemas and seborrhoea were treated with a hydrophilic ointment containing 0.2% pyridoxine-3,4- dipalmitate for seven to twenty days. This treatment was very effec- tive in six cases, satisfactory in six cases and ineffective in two cases. In three cases of seborrhoea and especially dermatitis of the face, patients felt a cooling sensation immediately after application sebum vanished day by day. In one case of rosacea (of the first degree), red- dening was reduced, oily luster vanished after ten days, and the disease was cured completely on the fourteenth day. In two cases of seborrhoea