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Arbutin(CAS No. 497-76-7)

Arbutin C12H16O7 (cas 497-76-7) Molecular Structure

497-76-7 Structure

Identification and Related Records

【Name】
Arbutin
【Iupac name】
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
【CAS Registry number】
497-76-7
【Synonyms】
.beta.-D-Glucopyranoside, 4-hydroxyphenyl
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
Arbutoside
Hydroquinone beta-D-glucopyranoside
2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
beta-D-Glucopyranoside, 4-hydroxyphenyl- (9CI)
hexopyranoside, 4-hydroxyphenyl
(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
beta-Arbutin
Ursin
Uvasol
4-hydroxyphenyl hexopyranoside
4-Hydroxyphenyl-beta-D-glucopyranoside
p-Hydroxyphenyl beta-D-glucopyranoside
(3R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
4-Hydroxyphenyl beta-D-glucopyranoside
4-hydroxyphenyl β-D-glucopyranoside
β-Arbutin
4-Hydroxyphenyl-β-D-glucopyranoside
【EINECS(EC#)】
207-850-3
【Molecular Formula】
C12H16O7 (Products with the same molecular formula)
【Molecular Weight】
272.2512
【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
【Canonical SMILES】
C1=CC(=CC=C1O)OC2C(C(C(C(O2)CO)O)O)O
【Isomers smiles】
C1=CC(=CC=C1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
【MOL File】
497-76-7.mol

Chemical and Physical Properties

【Appearance】
white powder
【Density】
1.556g/cm3
【Melting Point】
198-201℃
【Boiling Point】
561.6°C at 760 mmHg
【Vapour】
1.9E-13mmHg at 25°C
【Refractive Index】
1.65
【Flash Point】
293.4°C
【Alpha】
-64 o (C=3)
【Water】
10-15 g/100 mL at 20℃
【Solubilities】
50mg/mL in water
【Color/Form】
Colorless elongated prisms from moist ethyl acetate
White powder (pure synthetic)
Needles (water + 1)
【Stability】
Stable. Hygroscopic - store under dry nitrogen.
【HS Code】
29389090
【Spectral properties】
Specific optical rotation: -60.3 deg at 20 deg C/D (in water)
Specific optical rotation: -64 deg at 25 deg C/D (3% water)
IR: 18673 (Sadtler Research Laboratories IR grating collection)
UV: 4704 (Sadtler Research Laboratories spectral collection)
1H NMR: 4444 (Sadtler Research Laboratories spectral collection)
【Computed Properties】
Molecular Weight:272.25124 [g/mol]
Molecular Formula:C12H16O7
XLogP3:-0.7
H-Bond Donor:5
H-Bond Acceptor:7
Rotatable Bond Count:3
Tautomer Count:2
Exact Mass:272.089603
MonoIsotopic Mass:272.089603
Topological Polar Surface Area:120
Heavy Atom Count:19
Formal Charge:0
Complexity:279
Isotope Atom Count:0
Defined Atom Stereocenter Count:5
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:6
Feature 3D Donor Count:5
Feature 3D Ring Count:2
Effective Rotor Count:4.2
Conformer Sampling RMSD:0.6
CID Conformer Count:80

Safety and Handling

【Hazard Codes】
Xn
【Risk Statements】
R20/21/22
【Safety Statements 】
22-24/25-36-26
【Safety】

An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes:?HarmfulXn
Risk Statements: 20/21/22-36/37/38
20/ 21/22(Harmful by inhalation,in contact with skin and if swallowed)
36/37/38 (Irritating to the eyes piratory system and skin)
Safety Statements: 22-24/25-36-26
22(Do not breathe dust)
24/25(Avoid contact with skin and eyes)
36(Wear suitable protective clothing)
26 (In case of contact with eyes,rinse immediately with plenty of water and seek medical advice)
WGK Germany: 3
RTECS: CE8863000
F: 3-10-23

【Sensitive】
Hygroscopic
【Transport】
OTH
【Specification】

? Arbutin , with CAS number of 497-76-7, can be called (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol ; Arbutoside ; Hydroquinone-O-beta-D-glucopyranoside ; Hydroquinone .beta.-D-glucopyranoside ; p-Hydroxyphenyl beta-D-glucoside ; 4-Hydroxyphenyl-beta-D-glucopyranoside .?Arbutin (CAS NO.497-76-7) should be stored in a cool, dry place with?a tightly closed container.?

【Octanol/Water Partition Coefficient】
log Kow = -1.35
【Disposal Methods】
SRP: 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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Pure arbutin can be prepared synthetically from acetobromoglucose and hydroquinone in the presence of alkali

Biomedical Effects and Toxicity

【Therapeutic Uses】
/EXPL THER/ Although the toxicogenomics of A375 human malignant melanoma cells treated with arbutin have been elucidated using DNA microarray, the proteomics of the cellular response to this compound are still poorly understood. ...This study ... performed proteomic analyses to investigate the anticancer effect of arbutin on the protein expression profile in A375 cells. After treatment with arbutin (8 ug/mL) for 24, 48 and 72 hr, the proteomic profiles of control and arbutin-treated A375 cells were compared, and 26 differentially expressed proteins (7 upregulated and 19 downregulated proteins) were identified by MALDI-Q-TOF MS and MS/MS. Among these proteins, 13 isoforms of six identical proteins were observed. Bioinformatic tools were used to search for protein function and to predict protein interactions. The interaction network of 14 differentially expressed proteins was found to be correlated with the downstream regulation of p53 tumor suppressor and cell apoptosis. In addition, three upregulated proteins (14-3-3G, VDAC-1 and p53) and five downregulated proteins (ENPL, ENOA, IMDH2, PRDX1 and VIME) in arbutin-treated A375 cells were validated by RT-PCR analysis. These proteins were found to play important roles in the suppression of cancer development. [Nawarak J et al; Biochim Biophys Acta Oct 18 [Epub ahead of print] (2008)]
【Biomedical Effects and Toxicity】
The urinary excretion of arbutin metabolites was examined in a randomized crossover design in 16 healthy volunteers after the application of a single oral dose of bearberry leaves dry extract (BLDE). There were two groups of application using either film-coated tablets (FCT) or aqueous solution (AS). The urine sample analysis was performed by a validated HPLC coolarray method (hydroquinone) and a validated capillary electrophoresis method (hydroquinone-glucuronide, hydroquinone-sulfate). The total amounts of hydroquinone equivalents excreted in the urine from BLDE were similar in both groups. With FCT, 64.8% of the arbutin dose administered was excreted; with AS, 66.7% was excreted (p = 0.61). The maximum mean urinary concentration of hydroquinone equivalents was a little higher and peaked earlier in the AS group versus the FCT group, although this did not reach statistical significance (Cur max = 1.6893 umol/mL vs. 1.1250 umol/mL, p = 0.13; tmax (t midpoint) = 3.60 h vs. 4.40 hr, p = 0.38). The relative bioavailability of FCT compared to AS was 103.3% for total hydroquinone equivalents. There was substantial intersubject variability. No significant differences between the two groups were found in the metabolite patterns detected (hydroquinone, hydroquinone-glucuronide, and hydroquinone-sulfate). [Schindler G et al; J Clin Pharmacol 42 (8): 920-7 (2002)] PubMed Abstract
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 respectively; melanin 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 (PPubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL 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 deg 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).

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