4-[(2-Tetrahydropyranyl)oxy]phenol
Phenol, 4-[(tetrahydro-2H-pyran-2-yl)oxy]-
CAS: 53936-56-4
Molecular Formula: C11H14O3
4-[(2-Tetrahydropyranyl)oxy]phenol - Names and Identifiers
4-[(2-Tetrahydropyranyl)oxy]phenol - Physico-chemical Properties
| Molecular Formula | C11H14O3 |
| Molar Mass | 194.23 |
| Density | 1.174 |
| Melting Point | 88-89 °C(Solv: ligroine (8032-32-4)) |
| Boling Point | 349.8±32.0 °C(Predicted) |
| Flash Point | 165.341 °C |
| Solubility | DMSO : ≥ 100 mg/mL (514.85 mM);H2O : < 0.1 mg/mL (insoluble) |
| Appearance | White to off-white (Solid) |
| Color | White to Off-White |
| pKa | 10.10±0.15(Predicted) |
| Storage Condition | under inert gas (nitrogen or Argon) at 2-8°C |
| Stability | Hygroscopic |
| MDL | MFCD09970981 |
4-[(2-Tetrahydropyranyl)oxy]phenol - Reference
| Reference Show more | 1. [IF=6.312] Wei Wang et al."Kojic Acid Showed Consistent Inhibitory Activity on Tyrosinase from Mushroom and in Cultured B16F10 Cells Compared with Arbutins."Antioxidants-Basel. 2022 Mar;11(3):502 |
4-[(2-Tetrahydropyranyl)oxy]phenol - Reference Information
| a new generation of cosmetic skin whitening active agent | deoxyarbutin is a new generation of cosmetic skin whitening active agent, mainly used in advanced whitening cosmetics, it can effectively inhibit tyrosinase activity, regulate the production of melanin, overcome pigmentation, dilute black spots on the skin, and have a rapid and long-lasting skin whitening effect. Deoxyarbutin also has a strong antioxidant effect. The inhibitory effect of deoxyarbutin on tyrosinase is significantly better than other whitening agents. The whitening effect is 350 times that of arbutin, 150 times that of kojic acid, and 10 times that of hydroquinone. Compared with the former, it is safer and more stable. It is not only non-toxic and non-irritating to the skin, but also easily absorbed by the skin. It can show whitening and brightening effects with a small amount of use. It is considered a very safe cosmetic whitening agent. |
| efficacy and action | deoxyarbutin is a very effective tyrosinase inhibitory component, which has obvious blocking effect on melanin formation in skin. In animal skin tests, deoxyarbutin can effectively inhibit the activity of tyrosinase and the formation of melanin in skin tissues, quickly and effectively make the skin white, and have varying degrees of whitening effect on people of different skin colors. When using this ingredient, the effect can still be maintained for nearly 8 weeks. After 8 weeks of discontinuation, the decolorization effect can be completely reversed and will not cause permanent damage to melanocytes, its efficacy is 10 times that of hydroquinone and 350 times that of general arbutin. Therefore, as a new generation of cosmetic skin whitening agent, it is mainly used in advanced whitening cosmetics. Cosmetics as an additive have been listed in the United States, Taiwan and other places, and have a very broad application in the future whitening skin care market. In addition, in addition to whitening effects, it also has many other effects. It can be seen as an intermediate for synthetic compounds and synthetic liquid crystals. Cyclopeptide alkaloids (structural formula is shown in fig. 1) is a naturally occurring compound, which has outstanding effects on stabilizing and antibacterial. The material was fully synthesized by the Shanghai Organic Department of the Chinese Academy of Sciences as a key intermediate. In addition, this product and water, lecithin, higher fatty alcohols, non-ionic surfactants, etc. can form a new type of liquid crystal material. Because of its strong skin permeability, the liquid crystal material composed of this compound has a good effect on whitening skin. fig. 1 is the structural formula of Cyclopeptide alkaloids. |
| synthesis method | 1. direct etherification of hydroquinone: hydroquinone and 3, 4-dihydropyran are first dissolved in the solvent, and the solvent is slowly added at room temperature. Using Fe2(SO4) 3.xH2O as catalyst, deoxyarbutin can be directly obtained by reaction in acetone. The defect of this method is that the product needs column chromatography separation and purification, which is not conducive to industrial production. 2. Zhang Wenzheng used hydroquinone as a raw material, after hydroquinone monobenzyl etherification, and another phenolic hydroxyl group under the catalysis of self-made pyridyl p-toluene sulfonate, the tetrahydropyran etherification was successfully completed, and the benzyl group and tetrahydropyran were respectively protected hydroquinone was prepared in a higher yield, and finally deoxyarbutin was synthesized by catalytic hydrogenation. At the same time, different adsorbents including silica gel, calcium chloride, diatomite, activated carbon and sodium carbonate are added during the dehydrogenation process, and alkaline anhydrous sodium carbonate is finally selected, which can avoid the decomposition of the product under acidic conditions. The content of hydroquinone can be reduced to below 20ppm. The specific reaction route is as follows: Figure 2 is the reaction route for the synthesis of deoxyarbutin using hydroquinone as raw material. |
| characterization data | 1. infrared data IR(KBr),ν/cm? 1: 1102.56cm? 1(νC-O-C),3320.22cm? 1(ν-OH) 2. NMR 1H-NMR(CDCl3) δ(ppm): 1.62~1.66, (3H,m, tetrahydropyran ring hydrogen), 1.84~1.87(2H, q, tetrahydropyran ring hydrogen), 1.99(1H, s, tetrahydropyran ring hydrogen),3.59~3.61,3.93~3.97 (2H, O-CH2-C), 4.97 (1H, s, -C-OH), 5.28~5.29(1H, t, O-CH-O), 6.71~6.73(2H, d, benzene ring hydrogen),6.92~6.94 (2H, d, benzene ring hydrogen). 3. liquid phase data the compound of Ret Time 3.33 min is hydroquinone, and the compound of 10.27min is deoxyarbutin. the specific data are shown in fig. 3 and fig. 4. fig. 3 is the liquid phase spectrum of deoxyarbutin. Figure 4 shows the results of liquid chromatography analysis of deoxyarbutin. |
| safety | comparative tests on various whitening agents show that deoxyarbutin has the lowest cytotoxicity, and the skin desalination effect of this product is reversible, which is considered to be a very safe cosmetic whitening agent. |
| precautions | deoxyarbutin is easy to oxidize and is easy to change color in the presence of water. attention should be paid to the formula: 1. fill with nitrogen; 2. add antioxidant that can be compounded; 3. the heating temperature shall not be higher than 80 ℃, and it is best to add it to the low temperature phase; 4. fully study the formula to eliminate the influence of discoloration. |
Last Update：2024-04-09 20:49:11
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