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HCID 440936Erstellt: 27. Oktober 2026

4-Hydroxyphenyl-β-D-glucopyranosid

beta-arbutin · β-Arbutin · URSIN · b-Arbutin · UVASOL · rbutin · P-ARBUTIN · hydroquinone O-β-D-glucopyranoside

https://huagongshe.com/de/chemical/440936

Molekülstruktur von 4-Hydroxyphenyl-β-D-glucopyranosid

Identifikatoren & physikalische Daten

CAS No.497-76-7
SummenformelC12H16O7
Durchschnittliche Molmasse272,25 g/mol
Monoisotopische Masse272,08960285 g/mol
SMILESOC[C@H]1O[C@@H](Oc2ccc(O)cc2)[C@H](O)[C@@H](O)[C@@H]1O
InChIKeyBJRNKVDFDLYUGJ-RMPHRYRLSA-N
PubChem CID440936
ChEMBLCHEMBL232202
ChEBICHEBI:18305
EC No.207-850-3
DTXSIDDTXSID7040152
Lokaler Name4-Hydroxyphenyl-β-D-glucopyranosid

Chemische & physikalische Eigenschaften

XLogP-0,7
Polarare Oberfläche (TPSA)120
H-Brücken-Donoren5
H-Brücken-Akzeptoren7
Frei drehbare Bindungen3
Schwere Atome19
Formalladung0
Komplexität279
ArzneimittelPharmaceuticals -> Listed in ZINC15
KosmetikaSkin conditioningAntioxidant
SpringerMaterials PropertiesChemical shift
LogP (Verteilungskoeffizient)log Kow = -1.35
Color/FormColorless elongated prisms from moist ethyl acetateWhite powder (pure synthetic)Needles (water + 1)
Löslichkeit≥ 10g/100gSlightly soluble in ethyl etherinsoluble in benzene, chloroform, CS2Soluble in water and alcoholH2O: 50 mg/mL hot, clear10-15 g/100 mL at 20 ºC
Schmelzpunkt199 °C142 - 143 °C195-198 °C
Optical RotationCrystalizes from water as the monohydrate, mp 158-160 °Csolifidies and melts again at 175 °C. Also reported as unstable form, mp 160.5 °Cstable form, mp 176 °C. Specific optical rotation: -60.66 deg at 20 °C/D (in water). Soluble in hot water or alcoholslightly soluble in ether. /Methylarbutin/Specific optical rotation: -60.3 deg at 20 °C/D (in water)Specific optical rotation: -64 deg at 25 °C/D (3% water)
Physical DescriptionSolid
Collision Cross Section226.6 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID7040152]164.4 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]159.52 Ų [M+Na-2H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]162.95 Ų [M+Na]+ [CCS Type: TW
Other Experimental PropertiesMP 199 °C after sintering at 163-164 °C ... Also reported as unstable form, mp 165 °Cstable form, mp 199.5-200 °C
Siedepunkt375.31°C (rough estimate)
Dichte1.3582 (rough estimate)
Brechungsindex-65.5 ° (C=4, H2O)
LagerbedingungenInert atmosphere,Room Temperature
AggregatzustandSolid
pKa (Säurekonstante)10.10±0.15(Predicted)
FarbeWhite
Biologische Quellesynthetic or plant
Merck14,773
BRN89673
Henry-Konstante8.2×1013 mol/(m3Pa) at 25℃, HSDB (2015)
StabilitätStable. Hygroscopic - store under dry nitrogen.
Hauptanwendungenfood and beverages
Kosmetik-Inhaltsstoffe FunktionenANTIOXIDANTSKIN CONDITIONING - MISCELLANEOUSBLEACHING
InChI1S/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
InChIKeyBJRNKVDFDLYUGJ-RMPHRYRLSA-N
SMILESOC[C@H]1O[C@@H](Oc2ccc(O)cc2)[C@H](O)[C@@H](O)[C@@H]1O
LogP (Verteilungskoeffizient)-1.350
CAS Datenbank497-76-7(CAS DataBase Reference)
EPA chemische Informationen.beta.-D-Glucopyranoside, 4-hydroxyphenyl (497-76-7)

Sicherheit & Vorschriften

GHS-EinstufungThis chemical does not meet GHS hazard criteria for 98.6% (137 of 139) of all reports.Not ClassifiedAggregated GHS information provided per 139 reports by companies from 3 notifications to the ECHA C&L Inventory.
Regulatorische Informationen.beta.-D-Glucopyranoside, 4-hydroxyphenyl: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesNot Classified
EntsorgungsverfahrenSRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
WechselwirkungenArbutin, the beta-D-glucopyranoside of hydroquinone, is a skin whitening cosmetic ingredient. Compared with arbutin, hydroquinone is a more potent skin lightening agent, but shows cytotoxicity, nephrotoxicity, and genotoxicity. To evaluate whether skin microflora can hydrolyze arbutin to hydroquinone, we measured the hydrolytic activity of the main skin microflora: Staphylococcus epidermidis and Staphylococcus aureus. All strains hydrolyzed arbutin, with activities of 0.16-4.51 nmol/min/mg. The hydrolyzed hydroquinone showed more potent 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity and tyrosinase inhibition than arbutin. These findings suggest that normal skin microflora may increase the skin lightening effect of arbutin due to the antioxidant action of hydroquinone....This study ... presents evidence that cotreatment of aloesin and arbutin inhibits tyrosinase activity in a synergistic manner by acting through a different action mechanism. Aloesin or arbutin similarly inhibited enzyme activity of human- and mushroom-tyrosinases with an IC50 value of 0.1 or 0.04 mM, respectively. Lineweaver-Burk plots of the enzyme kinetics data showed that aloesin inhibited tyrosinase activity noncompetitively with a Ki value of 5.3 mM, whereas arbutin did it competitively (Maeda, 1996). We then examined whether cotreatment of these agents inhibits the tyrosinase activity in a synergistic manner. The results showed that 0.01 mM aloesin in the presence of 0.03 mM arbutin inhibited activity of mushroom by 80% of the control value and the reverse was also true. The inhibitory effects were calculated to be synergistic according to the Burgi method. Taken together, we suggest that aloesin along with arbutin inhibits in synergy melanin production by combined mechanisms of noncompetitive and competitive inhibitions of tyrosinase activity.

Anwendungen & Verwendung

Beschreibung

Arbutin is a β-D-glucopyranoside HQ derivative and a plant-derived compound found in the dried leaves of several plant species, including blueberry, cranberry, bearberry, and pear trees. It suppresses tyrosinase activity without altering RNA expression.

History

Arbutin is a hydroquinone compound with two epimers, α and β arbutin. The sources of α-arbutin and β-arbutin are completely different. β-arbutin can be prepared by plant extraction, plant cell culture, and artificial synthesis. Arbutin can relieve cough and asthma and has whitening effect. The Japanese cosmetics company Shiseido developed the arbutin as a whitening agent in the 1990s. Arbutin can not only reduce skin freckles, senile plaques, and chloasma but also relieve acne and improve healing after skin burns. Arbutin is the epimer of β-arbutin, and the spatial orientation of their glycosidic bonds is just the opposite. Alpha arbutin is generally prepared by different microbial enzymes. A molecule of glucose and a molecule of hydroquinone combine to form a molecule α-arbutin . Alpha arbutin improves ultraviolet burn scar. α-Arbutin can be used in a variety of skin whitening cosmetics since it is chemically stable.

Verwenden

Arbutin is a glycosylated hydroquinone extracted from bearberry plant. Arbutin is a known inhibitor of tyrosinase, which in turn prevents the formation of melanin. Arbutin is often used as a skin-ligh tening agent in cosmetic products.

UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4(SRC), determined from a log Kow of -1.35(2) and a regression-derived equation(3), indicates that arbutin is expected to have very high mobility in soil(SRC). Volatilization of arbutin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-19 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Arbutin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-12 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data were not available(SRC, 2008).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4(SRC), determined from a log Kow of -1.35(2) and a regression-derived equation(3), indicates that arbutin is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.2X10-19 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2008).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), arbutin, which has an estimated vapor pressure of 2.3X10-12 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase the ambient atmosphere. Particulate-phase arbutin may be removed from the air by wet or dry deposition(SRC). Arbutin does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
LebensmitteluntersuchungswerteArbutin-containing foods include marjoram, pears (fruit, juice, possible adulterant in quince products), Japanese pepper, potatoes (Solanum tuberosum) infected with fungi, foods of Native Canadians, honeys in Italy and Sardinia, and beverages. Significant amounts of arbutin levels were found in wheat products (1-10 ppm), pears (4-15 ppm), and coffee and tea (0.1 ppm)(1).Uva ursi is generally taken by adults as crushed leaf or powder, an infusion or cold macerations, and fluidextract, providing 400-840 mg arbutin per day. As the dry extract, 100-210 mg arbutin are supplied to the individual. It is also available as a capsule, tea, and tincture. It has been estimated that an individual who drinks up to 3 g of tea from uva ursi leaves (which contain up to 6% HQ glycosides) four times a day consumes ~720 mg arbutin (2.64 mmol~12 mg/kg bw). Exposure can also occur through the use of herbal mixtures that contain bearberry or Uva ursi(1).
Plant ConcentrationsArbutin is found in Arctostaphylos uva-ursi (L.) (Bearberry)Vaccinium vitis-idaea var. minus (Cowberry, lingen, lingonberry)Arbutus unedo L. (Arbutus, Strawberry tree)Chimaphila umbellata (L.) (King's Cure, Pipsissewa) and Turnera diffusa (Damiana) (1).
Soil Adsorption/MobilityThe Koc of arbutin is estimated as 4(SRC), using a log Kow of -1.35(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that arbutin is expected to have very high mobility in soil.
Natural Pollution SourcesA glucoside found in the leaves of the cranberry, blueberry amd manzanita shrubs, and in the roots, trunks and leaves of most pear speciesArbutin is contained in the leaves of Arctostaphylos uva-ursi (L.) (Bearberry)Vaccinium vitis-idaea var. minus (Cowberry, lingen, lingonberry)Arbutus unedo L. (Arbutus, Strawberry tree) and Turnera diffusa (Damiana) at 120,00090,000270,000 and 7,000 ppm, respectively(1). It is found in the Chimaphila umbellata (L.) (King's Cure, Pipsissewa) plant at 75,000 ppm(1).
Human Toxicity Excerpts/GENOTOXICITY/ Although arbutin is a natural product and widely used as an ingredient in skin care products, its effect on the gene expression level of human skin with malignant melanoma cells is rarely reported. We aim to investigate the genotoxic effect of arbutin on the differential gene expression profiling in A375 human malignant melanoma cells through its effect on tumorigenesis and related side-effect. The DNA microarray analysis provided the differential gene expression pattern of arbutin-treated A375 cells with the significant changes of 324 differentially expressed genes, containing 88 up-regulated genes and 236 down-regulated genes. The gene ontology of differentially expressed genes was classified as belonging to cellular component, molecular function and biological process. In addition, four down-regulated genes of AKT1, CLECSF7, FGFR3, and LRP6 served as candidate genes and correlated to suppress the biological processes in the cell cycle of cancer progression and in the downstream signaling pathways of malignancy of melanocytic tumorigenesis./ALTERNATIVE and IN VITRO TESTS/ To study the effects of aloesin and arbutin on normal cultured human melanocytes in synergetic method. Building up the system of cultured human melanocytes. The cultured melanocytes in vitro were treated with the mixture of aloesin and arbutin. The cell viability and tyrosinase activity was measured by MTT assay, utilization of L-Dopa as the substrate respectivelymelanin content was measured by image analysis system. Furthermore, the effects of the mixture on melanocytes were compared with that of aloesin and arbutin. The mixture of aloesin and arbutin showed an inhibition on tyrosinase activity of human melanocytes and reduced significantly melanin content. Between the mixture and the single use of aloesin or arbutin, there is significant difference (P<0.05). On the other hand, the mixture has little influence on melanocytes viability and there is negative significance. The mixture of aloesin and arbutin can significantly inhibit the tyrosinase activity and melanogenesis of cultured human melanocytes. It showed the effects of aloesin and arbutin in a synergistic manner./ALTERNATIVE and IN VITRO TESTS/ To discover safe and effective topical skin-lightening agents ... alkyl esters of the natural product gentisic acid (GA) ... , four putative tyrosinase inhibitors, /were evaluated/ utilizing mammalian melanocyte cell cultures and cell-free extracts. Desirable characteristics include the ability to inhibit melanogenesis in cells (IC50 less than 100 ug/mL) without cytotoxicity, preferably due to tyrosinase inhibition. Of the six esters synthesized, the smaller esters (e.g. methyl and ethyl) were more effective enzyme inhibitors (IC50 approximately 11 and 20 ug/mL, respectively). For comparison, hydroquinone (HQ), a commercial skin "bleaching" agent, was a less effective enzyme inhibitor (IC50 approximately 72 ug/mL), and was highly cytotoxic to melanocytes in vitro at concentrations substantially lower than the IC50 for enzymatic inhibition. Kojic acid was a potent inhibitor of the mammalian enzyme (IC50 approximately 6 ug/mL), but did not reduce pigmentation in cells. Both arbutin and magnesium ascorbyl phosphate were ineffective in the cell-free and cell-based assays... .
Artificial Pollution SourcesArbutin's production and use as oxidation inhibitor, polymerization inhibitor, color stabilizer in photography, intermediate(1), an ingredient in cosmetics(2) and as an herbal medication(3) may result in its release to the environment through various waste streams(SRC).
Environmental BioconcentrationAn estimated BCF of 3 was calculated in fish for arbutin(SRC), using a log Kow of -1.35(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Volatilization from Water/SoilThe Henry's Law constant for arbutin is estimated as 1.2X10-19 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that arbutin is expected to be essentially nonvolatile from water surfaces(2). Arbutin's Henry's Law constant indicates that volatilization from moist soil surfaces may not occur(SRC). Arbutin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-12 mm Hg(SRC), determined from a fragment constant method(3).
Non-Human Toxicity Excerpts/GENOTOXICITY/ Arbutin (hydroquinone-beta-D-glucopyranoside) is present in various food plants. Its aglycone, hydroquinone, is mutagenic and carcinogenic. We investigated whether hydroquinone may be released under conditions encountered in the human gastrointestinal tract. Arbutin was stable in artificial gastric juice. Fecal slurries from nine human subjects completely converted arbutin (2 mM) into hydroquinone. Four of nine representative human intestinal species investigated, namely Eubacterium ramulus, Enterococcus casseliflavus, Bacteroides distasonis, and Bifidobacterium adolescentis, deglycosylated arbutin at rates of 21.08, 16.62, 8.43 and 3.59 nmol/min/(mg protein), respectively. In contrast, homogenates from small intestinal mucosa and cytosolic fractions from colon mucosa deglycosylated arbutin at substantially lower rates: 0.50 and 0.09 nmol/min/(mg protein), respectively. Arbutin, unlike hydroquinone, did not induce gene mutations in Chinese hamster V79 cells in the absence of an activating system. However, in the presence of cytosolic fractions from E. ramulus or B. distasonis, arbutin was strongly mutagenic. Cytosolic fraction from Escherichia coli, showing no arbutin glycosidase activity, was not able to activate arbutin in this model system. The release of the proximate mutagen hydroquinone from arbutin by intestinal bacteria in the immediate vicinity of the colon mucosa may pose a potential risk.
Environmental Abiotic DegradationThe rate constant for the reaction of arbutin with hydroxyl radicals in aqueous solutions is 3.1X10+9 L/mol-sec(1)this corresponds to an aquatic half-life of 260 days at an aquatic concentration of 1X10-17 hydroxyl radicals per liter(2). Arbutin is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Arbutin does not contain chromophores that absorb at wavelengths >290 nm(3) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
F3-10-23
Wassergefährdungsklasse (WGK)3
Zollcode29389090
RTECS-Nr.CE8863000
R-Sätze (R)20/21/22-36/37/38
GefahrensymboleXn
Sicherheitshinweise (S)22-24/25-36-26
Lagerklasse11 - Combustible Solids
Gefahrstoffdaten497-76-7(Hazardous Substances Data)