4-hydroxyphenyl β-D-galactopyranoside
Arbutin
CAS: 497-76-7
Molecular Formula: C12H16O7
4-hydroxyphenyl β-D-galactopyranoside - Names and Identifiers
| Name | Arbutin |
| Synonyms | Arbutin -Arbutin Arbutosie p-arbutin beta-arbutin Arbutin (natural) Hydroquinone glucose arbutin,beta-arbutin 4-hydroxyphenyl hexopyranoside 4-(β-D-Glucopyranosyloxy)phenol Hydroquinone β-D-glucopyranoside Hydroquinone-beta-D-glucopyranoside 4-hydroxyphenyl β-D-galactopyranoside 4-hydroxyphenyl-beta-d-glucopyranosid 4-hydroxyphenyl-beta-d-glucopyranoside 4-hydroxyphenyl beta-D-glucopyranoside 4-HYDROXYPHENYL-BETA-D-GLUCOPYRANOSIDE 4-hydroxyphenyl beta-D-galactopyranoside 4-hydroxyphenyl beta-D-glycero-hexopyranoside |
| CAS | 497-76-7 |
| EINECS | 207-850-3 |
| InChI | InChI=1/C12H16O7/c13-5-8-9(15)10(16)11(17)12(19-8)18-7-3-1-6(14)2-4-7/h1-4,8-17H,5H2/t8-,9+,10+,11-,12-/m1/s1 |
| InChIKey | BJRNKVDFDLYUGJ-RMPHRYRLSA-N |
4-hydroxyphenyl β-D-galactopyranoside - Physico-chemical Properties
| Molecular Formula | C12H16O7 |
| Molar Mass | 272.25 |
| Density | 1.3582 (rough estimate) |
| Melting Point | 195-198°C |
| Boling Point | 375.31°C (rough estimate) |
| Specific Rotation(α) | -64 º (c=3) |
| Flash Point | 293.4°C |
| Water Solubility | 10-15 g/100 mL at 20 ºC |
| Solubility | Insoluble in chloroform, ether, petroleum ether, etc. |
| Vapor Presure | 1.9E-13mmHg at 25°C |
| Appearance | White needle crystal |
| Color | White |
| Merck | 14,773 |
| BRN | 89673 |
| pKa | 10.10±0.15(Predicted) |
| Storage Condition | Inert atmosphere,Room Temperature |
| Stability | Stable. Hygroscopic - store under dry nitrogen. |
| Sensitive | Hygroscopic |
| Refractive Index | -65.5 ° (C=4, H2O) |
| MDL | MFCD00016915 |
| Physical and Chemical Properties | Melting Point 198-201°C specific optical rotation -64 ° (c = 3) water-soluble 10-15g/100 mL at 20°C |
| Use | Medicine used as diuretics, urinary system anti-infective drugs, also used as color photography development stabilizer, used in cosmetics for whitening, freckle, hair care, etc |
4-hydroxyphenyl β-D-galactopyranoside - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| RTECS | CE8863000 |
| FLUKA BRAND F CODES | 3-10-23 |
| HS Code | 29389090 |
4-hydroxyphenyl β-D-galactopyranoside - Reference
| Reference Show more | 1. Meng Xiaobin, Qu, color red. Determination of arbutin in arbutin cream by HPLC [J]. China pharmacy 2013 024(031):2944-2946. 2. Fu Shihui, Zhu Wenxue. Preliminary Study on the extraction process of arbutin and its antioxidant activity in vitro [J]. Journal of Henan University of Science and Technology: natural science, 2017, 38(005):55-59. 3. Pu Yuehua, Tong Yinhong. Study on whitening mechanism of hydrolyzed Pearl [J]. Spices and fragrances, 2015(03):43-46. 4. Xu Cuicui, Kong Hao, Guo Qingmei, etc. Study on the inhibitory effect of Trichosanthes extract on tyrosinase [J]. Journal of Sichuan Agricultural University, 2014, 26 (01):59-62. 5. Qu Caihong, Mai Haiyan, Xie Yang, etc. Simultaneous determination of arbutin and phloretin in compound quban cream by HPLC [J]. China Science and Technology of Traditional Chinese Medicine, 2014, 21(003):276-278. 6. Tang Cui, Wang Mingli, Zhao Yan, et al. Study on deacidification technology and activity of high acid value wheat bran oil [J]. China Oils and fats, 2017, 42(003):18-23. 7. Feng Lunyuan, He Lanping, Cui-Qin Li, et al. Screening of microbial β-glucosidase for hydrolyzing ginkgo flavone glycosides from traditional fermented soybean products in Guizhou [J]. Journal of Microbiology, 2020(2). 8. Yanbin Su, Xuwei Sun, Ruixue Wu, Xing Zhang & Yunzhou Tu (2020) Molecular radiological behaviors of beta-arbutin in anti-skin cancer, spectrum scopes, 53:3, 172-183, DOI: 10.1080/00387010.2020.1715441 9. Nan, Xingmei, et al. "Bioactive fraction of Rhodiola algida against chronic hypoxia-induced pulmonary arterial hypertension and its anti-proliferation mechanism in rats." Journal of ethnopharmacology 216 (2018): 175-183.https://doi.org/10.1016/j.jep.2018.0 10. [IF=4.142] Ji Wenhua et al."Superhydrophilic molecularly imprinted polymers based on a single cross-linking monomer for the recognition of iridoid glycosides in Di-huang pills."Anal Bioanal Chem. 2018 Oct;410(25):6539-6548 11. [IF=9.783] Huiping Bi et al."Biosynthesis of a rosavin natural product in Escherichia coli by glycosyltransferase rational design and artificial pathway construction."Metab Eng. 2022 Jan;69:15 12. [IF=2.72] Mengnan Hong et al."Characterization of tolerance and multi-enzyme activities in non-Saccharomyces yeasts isolated from Vidal blanc icewine fermentation."J Food Biochem. 2019 Nov;43(11):e13027 |
4-hydroxyphenyl β-D-galactopyranoside - Introduction
Pharmacological effects: used in advanced cosmetics, can be made into skin cream, anti-spot cream, high-grade pearl cream, etc., which can not only beautify skin care, but also reduce inflammation and anti-irritation. As the raw material of burn and scald medicine, the raw material of intestinal anti-inflammatory medicine.
Last Update：2022-10-16 17:25:29
4-hydroxyphenyl β-D-galactopyranoside - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| ideal whitening agent for whitening cosmetics | arbutin is also called arbutin, arbutin, arbutin, arbutin or myricin. because it originated from natural green plants, it is a skin whitening active substance integrating the concepts of "green", "safety" and "high efficiency. Arbutin is an ideal whitening agent for whitening cosmetics. There are two optical isomers, namely α and ß, and the β isomer with biological activity. It is white with light yellow powder at room temperature, easily soluble in water, methanol, ethanol, propylene glycol, glycerin aqueous solution, no precipitation solution after dissolution, and insoluble in chloroform, ether, petroleum ether, etc. It is added in many whitening products. It was named because it was found in the leaves of the bear fruit plant of the Rhododendron family, and later in the Vaccinium plant of the Rhododendron family, the pear tree (western pear, small mountain pear), and the leaves of the Saxifraga plant of the Saxifraga family. It was found in the leaves and used as a drug and cosmetic additive after extraction. arbutin is one of the safest and most effective whitening materials popular abroad at present, and it is also the most competitive skin whitening and freckle removing agent in the 21st century. In cosmetics, the skin can effectively whiten and remove freckle, gradually fade and remove freckles, chloasma, melanin, acne and age spots on the skin. High safety, no side effects such as irritation and sensitization, good compatibility with various components of cosmetics, and stable ultraviolet radiation. But arbutin is easy to hydrolyze and should be used under the condition of pH 5-7. In order to stabilize the performance, an appropriate amount of antioxidants such as sodium bisulfite and vitamin E are usually added to better realize whitening, freckle removal, moisturizing, softening, wrinkle removal and anti-inflammatory effects. It can be used to eliminate redness and swelling, promote wound healing without leaving scars, and inhibit the formation of dandruff. |
| ursolic acid and α-arbutin | ursolic acid is a triterpenoid compound existing in natural plants, which has sedative, anti-inflammatory, antibacterial, anti-diabetic, anti-ulcer, lowering blood sugar and other biological effects. In recent years, it has been found that it has anti-carcinogenic, anti-cancer, induction of F9 teratoma cell differentiation and anti-angiogenesis effects, and it is very likely to become a new anti-cancer drug with low toxicity and high efficiency. In addition, ursolic acid has obvious antioxidant function, so it is widely used as a raw material for medicine and cosmetics. α-arbutin can repair skin damage caused by ultraviolet rays, recall the skin's transparency, and is not easy to be decomposed by β-glucosidase on the skin surface. The effect is about 10 times that of β-arbutin. It can stay in every corner of the skin for a long time and continuously protect the skin from harm. Melanin is the cause of dull skin. α-arbutin can quickly penetrate deep into the skin and inhibit the activity of tyrosinase in pigment mother cells deep in the stratum corneum. And form a double effect on the skin surface to inhibit the production of melanin. |
| is it suitable for daytime use? | arbutin reduces the production of melanin by inhibiting the activity of tyrosinase, an enzyme that produces melanin. its principle of action is similar to that of the whitening drug hydroquinone. However, hydroquinone has side effects and many precautions, which must be used under the guidance and monitoring of doctors. However, arbutin has more glucose molecules than hydroquinone in its structure, has lower irritation, and can be freely added to skin care products, with an upper concentration limit of 7%. The active molecule of arbutin can penetrate the basal layer for deep spot lightening. It has a strong therapeutic effect on chloasma, black spot, sunburn, and pigmentation left by drug allergy, but if the concentration is too low, its effect The persistence will be weakened, so 5% concentration is the safest and most efficient spot lightening concentration, 5% concentration is faster than vitamin C spot lightening effect, and the persistence of spot lightening is stable, it will not have an irritating effect on the skin. Arbutin will be reduced to hydroquinone after being absorbed by the skin, which has caused some people to doubt the safety of arbutin, and believe that arbutin still has a chance to produce side effects similar to hydroquinone. The most commonly heard saying is that "skin care products containing arbutin cannot be used during the day, otherwise whitening will not be achieved, but darker". in fact, there is no need to worry. tests show that only arbutin with a concentration of more than 7% is likely to be sensitive to light, so 7% is a safety critical point. there are clear regulations on the addition of ingredients in skin care products. the upper limit of the maximum concentration is 7%. within this concentration range, arbutin is not enough to produce photosensitivity and cannot be used without light. Absorbed by the skin and decomposed by light, it will be reduced to hydroquinone, resulting in a whitening effect. The concentration of hydroquinone contained in arbutin maintenance products is less than 20ppm (that is, 20 parts per million). Under such a low concentration limit, hydroquinone will not cause side effects such as skin blackening. If you dare not use arbutin during the day just because the care products contain arbutin, it is unnecessary, unless the care products containing arbutin are also added with other maintenance ingredients that need to avoid light. In short, you should buy reliable brand care products, and then no matter what you apply, you should do a good job of sunscreen during the day. |
| use | medically used as diuretics, urinary system anti-infective drugs, also used as color photography development stabilizer, used in cosmetics for whitening, freckle removal, hair care, etc. a glycosylated hydroquinone, used to study melatonin biosynthesis and as an inhibitor for identifying, distinguishing and identifying tyrosinase. Arbutin is a glycosylated hydroquinone extracted from bear fruit plants. Arbutin is a known tyrosinase inhibitor, which in turn prevents the formation of melanin. Arbutin is often used as a whitening agent for cosmetics. Inhibition of melanocyte tyrosinase activity, inhibition of melanin production by inhibiting melanin synthase. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:01:54
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