What is Deoxyarbutin?
Deoxyarbutin, as a competitive Tyrosinase inhibitor, can regulate the production of melanin, overcome pigmentation, fade skin black spots, and have a rapid and lasting skin whitening effect.
The inhibitory effect of deoxyaarbutin on Tyrosinase is obviously superior to other whitening activators, and the whitening and brightening effect can be achieved with a small amount of use. Deoxyarbutin also has strong antioxidant effects.
- Chinese name Deoxyarbutin
- Foreign name Deoxyarbutin
- Nickname p – (tetrahydro-2H-pyran-2-oxy) phenol
- Chemical formula C11H14O3
- Molecular weight 194.23
- CAS login number 53936-56-4
- English alias 4- [(Tetrahydro-2H-pyran-2-yl) oxy] phenol
- Purity ≥ 98%
Deoxyarbutin as a new generation of cosmetic brightening and whitening active agent, is mainly used in advanced whitening cosmetics.
Modulation of melanogenesis in the melanocytes can be achieved using chemicals that share structural homologies with the substrate tyrosine and as thus competitively inhibit the catalytic function of tyrosinase.
We have developed a new tyrosinase inhibitor, deoxyArbutin (dA), based on this premise.
DeoxyArbutin demonstrates effective inhibition of mushroom tyrosinase in vitro with a Ki that is 10-fold lower that hydroquinone (HQ) and 350-fold lower than arbutin. In a hairless, pigmented guinea pig model, dA demonstrated rapid and sustained skin lightening that was completely reversible within 8 weeks after halt in topical application.
In contrast, HQ induced a short but unsustained skin lightening effect whereas kojic acid and arbutin exhibit no skin lightening effect. Results from a panel of safety tests supported the overall establishment of dA as an actionable molecule.
In a human clinical trial, topical treatment of dA for 12 weeks resulted in a significant or slight reduction in overall skin lightness and improvement of solar lentigines in a population of light skin or dark skin individuals, respectively.
These data demonstrate that dA has potential tyrosinase inhibitory activity that can result in skin lightening and may be used to ameliorate hyperpigmentary lesions.
Melasma (chloasma) is a common skin pigmentary disorder characterized by irregular light to darkbrown patches on the face, which usually cause significant psychiatric and psychological burdens for affected individuals. However, the inciting events for the pathogenesis of melasma are not well understood.
Melasma is more common in persons with Fitzpatrick skin types IV through VI than in those with fairer skin (types I through III).
Melasma is also recognized to be more common among women than men and more common among Asians, Latinos and African-Americans than among Caucasians. An estimated 50% to 70% of pregnant women in the US develop melasma.
It has been established that the hyperactive melanocytes in melasma skin produce much more melanin pigment via the tyrosine catabolism pathway.
Tyrosinase (EC 220.127.116.11), a copper-containing glycoprotein, is the rate-limiting enzyme critical for this pathway. Melanin synthesis occurs within highly specialized organelles termed melanosomes and then melanized melanosomes are transferred from melanocytes to neighboring keratinocytes, thereby determining constitutive and facultative skin color. Many skin lightening agents are targeted on controlling melanin synthesis via the suppression of tyrosinase activity .
Over the past50years, hydroquinone (1, 4-benzenediol, HQ) has been widely used as the gold standard for prototypical tyrosinase inhibitors in treating melasma. However, much recent attention has been paid to the potential health risk of long term exposure to HQ, such as exogenous ochronosis, leukoderma (occupational vitiligo), and even carcinogenesis .It is generally accepted that HQ presumably acts as a substrate to competitively inhibit tyrosinase activity, granting the potential of skin whitening.
Meanwhile, these monophenol compounds also give rise, through the enzymatic oxidation by tyrosinase, to abundant free radicals that cause lipid peroxidation and consequent melanosomal membrane damages.
In previous studies from our laboratory it has been shown that deoxyarbutin (4-[(tetrahydro-2H-pyran-2-yl) oxy] phenol, D-Arb), a glucoside derivative of HQ, is safer and less cytotoxic when compared to its mother compound hydroquinone .
The present study was undertaken to investigate the toxicity and efficacy of D-Arb at the sub-cellular level (directly on melanosomes) and skin pigmentation using in vivo and in vitro models, further evaluating the biosafety of D-Arb in parallel comparison with HQ for skin lightening use.
Deoxyarbutin, as a new generation of cosmetic brightening and whitening active agent, is mainly used in advanced whitening cosmetics.
D-Arbutin is one of the derivatives of Arbutin, called D-nenenebb arbutin, which can effectively inhibit the action of tyrosinase in skin tissue.
According to research, its effect is even 10 times that of hydroquinone and 350 times that of general Arbutin. In animal skin tests, this D-Arbutin can quickly and effectively whiten the skin, and after discontinuing use, the effect can still be maintained for nearly 8 weeks.
In clinical studies on the human body, topical use of D-Arbutin for 12 weeks can achieve significant skin lightening effects, and it has a good improvement effect on daily light exposure spots and dark skin conditions.