Table 13.

An anti-tyrosinase activity of hydroxybenzoic and hydroxycinnaminic acids and their derivatives (NR-not reported; a-L-DOPA; b-L-tyrosin).

Substances	Substrate	Positive control (inhibitor)	Type of inhibition	Inhibition constant ${\mathrm{K}}_{\mathrm{i}}$ (mM)	Source of tyrosinase	The half-maximal inhibitory concentration ${\mathrm{IC}}_{50}$(mM)	References
Hydroxybenzoic acids
Anisic acid (p-methoxybenzoic acid)	L- DOPA	NR	Non-competitive	0.603	Mushroom	0.6	Kubo et al.90
p-Hydroxybenzoic acid	L- DOPA	NR	Competitive	0.73	Mushroom	1.3	Kubo et al.90
p-Methoxybenzoic acid	L- DOPA	NR	Non-competitive	0.43/0.43	Mushroom	0.42	Chen et al.92
p-Ethoxybenzoic acid	L- DOPA	NR	Non-competitive	NR	Mushroom	NR	Kubo et al.90
	L- DOPA	NR	Mixed	1.46/0.84	Mushroom	1.1	Chen et al.92
p-Propoxybenzoic acid	L- DOPA	NR	Mixed	NR	Mushroom	NR	Kubo et al.90
	L- DOPA	NR	Non-competitive	0.84	Mushroom	1.85	Kubo et al.90
p-Butoxybenzoic acid	L- DOPA	NR	Competitive	NR	Mushroom	NR	Kubo et al.90
	L- DOPA	NR	Non-competitive	0.71	Mushroom	1.65	Chen et al.92
p-Pentyloxybenzoate acid	L- DOPA	NR	Non-competitive	0.6	Mushroom	1.4	Kubo et al.90
p-Hexyloxybenzoic acid	L- DOPA	NR	Non-competitive	0.49	Mushroom	1.15	Chen et al.92
Gallic acid	L- DOPA	NR	NR	NR	Mushroom	4.5	Kubo et al. 94
Methyl gallate	L- DOPA	NR	NR	NR	Mushroom	0.35	Kubo et al. 94
Propyl gallate	L- DOPA	NR	NR	NR	Mushroom	0.31	Kubo et al. 94
Hexyl gallate	L- DOPA	NR	NR	NR	Mushroom	0.21	Kubo et al. 94
Octyl gallate	L- DOPA	NR	NR	NR	Mushroom	0.33	Kubo et al. 94
Decyl gallate	L- DOPA	NR	NR	NR	Mushroom	0.28	Kubo et al. 94
Dodecyl gallate	L- DOPA	NR	Mixed	NR	Mushroom	0.49	Kubo et al. 94
Hydroxycinnaminic acids
Cinnamic acid	L- DOPA	NR	Non-competitive	1.99	Mushroom	2.1	Shi et al.95
2-Hydroxycinnamic acid	L- DOPA	NR	Not effective	Not effective	Mushroom	Not effective	Shi et al.95
4-Hydroxycinnamic acid	L- DOPA	NR	Competitive	0.244	Mushroom	0.5	Shi et al.95
4-Methoxycinnamic acid	L- DOPA	NR	Non-competitive	0.458	Mushroom	0.42	Shi et al.95
3,4-Dihydroxycinnamic acid	L- DOPA	NR	Non-competitive	NR	Mushroom	0.33	Garcia-Jimenez et al.96
4-Hydroxy-3-methoxycinnamic acid	L- DOPA	NR	Non-competitive	NR	Mushroom	0.33	Garcia-Jimenez et al.96
2-Methoxycinnamic acid	L- DOPA L-Tyrosine	NR	Competitive	${0.51}^a$/${0.5}^b$	Mushroom	NR	Garcia-Jimenez et al.96
3-Methoxycinnamic acid	L- DOPA L-Tyrosine	NR	Competitive	${0.68}^a$/${0.69}^b$	Mushroom	NR	Garcia-Jimenez et al.96
4-Methoxycinnamic acid	L- DOPA L-Tyrosine	NR	Competitive	${1.47}^a$/${1.54}^b$	Mushroom	NR	Garcia-Jimenez et al.96
Protocatechuic acid methyl ester	L-Tyrosine	NR	NR	NR	Mushroom	NR	Miyazawa et al.93
Protocatechuic acid	L-Tyrosine	NR	NR	NR	Mushroom	NR	Miyazawa et al.93
Vanillic acid	L-Tyrosine	NR	NR	NR	Mushroom	NR	Miyazawa et al.93
Vanillic acid methyl ester	L-Tyrosine	NR	NR	NR	Mushroom	NR	Miyazawa et al.93
Isovanillic acid	L-Tyrosine	NR	NR	NR	Mushroom	NR	Miyazawa et al.93
Isovanillic acid methyl ester	L-Tyrosine	NR	NR	NR	Mushroom	NR	Miyazawa et al.93
Veratric acid	L-Tyrosine	NR	NR	NR	Mushroom	NR	Miyazawa et al.93
Veratric acid methyl ester	L-Tyrosine	NR	NR	NR	Mushroom	NR	Miyazawa et al.93
Ferulic acid	L-Tyrosine	Hydroquinone	NR	NR	Mushroom	NR	Maruyama et al.97
Caffeic acid	L-Tyrosine	Hydroquinone	NR	NR	Mushroom	NR	Maruyama et al.97
p-Coumaric acid	L-Tyrosine	Kojic acid Arbutin	NR	NR	Mushroom	0.115	Maruyama et al.97