Condensation Reaction of 3- [(8Z) -8-Pentadecenyl] Phenol and 3- [(8Z, 11Z) -8, 11, 14-Pentadecatrienyl] Phenol with Several Indoles and Their Application to Whitening Effects Utility

Antimicrobial and Tyrosinase Inhibitory Activities of 6-[(8Z)-8-Pentadecenyl]salicylic Acid Derivatives.

“…In addition, [1] was found to be antimicrobial with a MIC of 3.13 mg/mL against Sm, a gram-positive coccus that plays a highly important role in the etiology of dental caries; and with a MIC of 6.25 mg/mL against Bt, a kind of aerobic bacillus, and the nonpathogenic Bs. By contrast, [2] had antimicrobial activity with a MIC ranging from 6.25 to 12.5 mg/mL against Bs, Ba, Bt and Pac. The triol compound [3] showed antimicrobial activity with a MIC ranging from 25 to 50mg/mL against Bs, Ba, Bt, Pac and Sa.…”

“…In the test for antimicrobial activity, [1] and [2] showed activity with a minimal inhibitory concentration (MIC) of 0.39 mg/mL and 6.25 mg/mL, respectively, against Pac, an organism that has been considered to be causal in liver disease. In addition, [1] was found to be antimicrobial with a MIC of 3.13 mg/mL against Sm, a gram-positive coccus that plays a highly important role in the etiology of dental caries; and with a MIC of 6.25 mg/mL against Bt, a kind of aerobic bacillus, and the nonpathogenic Bs.…”

“…5, which showed that inhibition did not take place at the level of the interme-diate formed in the tyrosinase reaction but was a competitive process; that is, these compounds competed with the substrate, L-DOPA, for the active site of tyrosinase. From this observation, it was inferred that the type of compounds that have an optimal inhibitory effect on tyrosinase activity would be those with an oorientation in which the -COOH group and the -OH group can easily form an intramolecular hydrogen bond on the aromatic ring; in addition, it would be necessary [2] 12.5 12.5 12.5 6.25 100 50 800 800 800 800 800 800 800 400 [3] 50 50 25 50 50 100 800 800 800 800 800 800 800 800 [4] 400 400 400 400 400 3200 800 800 800 800 400 400 400 200 [8] 800 800 800 800 800 800 800 800 800 800 800 800 800 800 [5] 400 400 400 800 800 800 800 800 800 800 800 800 800 400 [6] 400 800 400 400 800 800 800 800 800 800 400 400 400 200 [7] 800 800 800 800 800 800 800 800 800 800 800 800 800 800 K. Kasemura, M. Noumura, T. Tada et al to introduce the -OH group into the monoolefin present in the C 15 side chain at the C 8 position, which would probably lead to a high percentage of inhibition. These noble derivatives, which showed strong inhibition of tyrosinase, were examined for their inhibition of melanogenesis and toxicity in B-16 melanoma cells.…”

“…Calcium hydroxide (3 g) was added, and the mixture was shaken until neutralized. Chromatography of the residue (1.42 g) on silica gel and elution with ether gave 1.03 g (57% yield) of crystalline compound [2]. m.p.…”

“…The flask was immersed in a oil bath at 30 , and 25mL of a mixture of acetone, water and formic acid (65:32:3) was introduced into the reaction, followed by 0.36g (1 mmol) of compound [2]. The reaction mixture was stirred vigorously.…”