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Prestwick3_001026

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Chemistry

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Also known as: 497-76-7, Arbutoside, Ursin, Uvasol, P-arbutin, Beta-arbutin

Molecular Formula

C₁₂H₁₆O₇

Molecular Weight

272.25 g/mol

InChI Key

BJRNKVDFDLYUGJ-RMPHRYRLSA-N

FDA UNII

C5INA23HXF

-arbutin is a natural product found in Grevillea robusta, Halocarpus biformis, and other organisms with data available.

1 2D Structure

Arbutin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol

2.1.2 InChI

InChI=1S/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

2.1.3 InChI Key

BJRNKVDFDLYUGJ-RMPHRYRLSA-N

2.1.4 Canonical SMILES

C1=CC(=CC=C1O)OC2C(C(C(C(O2)CO)O)O)O

2.1.5 Isomeric SMILES

C1=CC(=CC=C1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

2.2 Other Identifiers

2.2.1 UNII

C5INA23HXF

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 497-76-7

2. Arbutoside

3. Ursin

4. Uvasol

5. P-arbutin

6. Beta-arbutin

7. 4-hydroxyphenyl Beta-d-glucopyranoside

8. P-hydroxyphenyl Beta-d-glucoside

9. 4-hydroxyphenyl-beta-d-glucopyranoside

10. Arbutinum

11. P-hydroxyphenyl Beta-d-glucopyranoside

12. Ursi

13. Hydroquinone-o-beta-d-glucopyranoside

14. Hydroquinone Beta-d-glucopyranoside

15. Ericolin

16. Hydroquinone O-beta-d-glucopyranoside

17. Hydroquinone-glucose

18. Hydroquinone

19. A-d-glucopyranoside

20. (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol

21. (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)tetrahydro-2h-pyran-3,4,5-triol

22. C5ina23hxf

23. 4-hydroxyphenyl-.beta.-d-glucopyranoside

24. Chembl232202

25. Chebi:18305

26. Hydroquinone Glucose

27. Nsc-4036

28. Arbutine

29. Arbutyne

30. Hydroquinone-beta-d-glucopyranoside

31. Dsstox_cid_20152

32. Dsstox_rid_79450

33. Dsstox_gsid_40152

34. Nsc 4036

35. Mfcd00016915

36. (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)tetrahydropyran-3,4,5-triol

37. (2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-(4-oxidanylphenoxy)oxane-3,4,5-triol

38. Cas-497-76-7

39. Sr-05000002157

40. Unii-c5ina23hxf

41. Ccris 9273

42. B-arbutin

43. Hsdb 7661

44. Uva,p-arbutin

45. Ncgc00095599-01

46. Einecs 207-850-3

47. Beta-d-glucopyranoside, 4-hydroxyphenyl

48. Brn 0089673

49. Spectrum_000786

50. Specplus_000314

51. Arbutin [hsdb]

52. Arbutin [inci]

53. Arbutin, >=98%

54. Arbutin [mi]

55. Arbutinum [hpus]

56. Arbutin [mart.]

57. Prestwick3_001026

58. Spectrum2_000662

59. Spectrum3_001233

60. Spectrum4_001474

61. Spectrum5_000147

62. Arbutin [who-dd]

63. Bmse000365

64. Arbutin (uva, P-arbutin)

65. Arbutin, Analytical Standard

66. Schembl36351

67. Arbutin - Uva - P-arbutin

68. Bspbio_001211

69. Bspbio_002706

70. Hydroquinone-beta-d-glucoside

71. Kbiogr_002047

72. Kbioss_001266

73. Spectrum300539

74. 5-17-07-00110 (beilstein Handbook Reference)

75. Mls002207046

76. Divk1c_006410

77. Spbio_000723

78. Bpbio1_001333

79. Megxp0_001504

80. Dtxsid7040152

81. Kbio1_001354

82. Kbio2_001266

83. Kbio2_003834

84. Kbio2_006402

85. Kbio3_002206

86. Hydroquinone O--d-glucopyranoside

87. Hms2098m13

88. Hms3715m13

89. P-hydroxyphenyl Beta -d-glucoside

90. Zinc518554

91. Hy-n0192

92. 4-hydroxyphenyl-beta-glucopyranoside

93. Hydroquinone Beta -d-glucopyranoside

94. Tox21_111509

95. Tox21_302428

96. B-d-glucopyranoside, 4-hydroxyphenyl

97. Bdbm50219502

98. Ccg-38565

99. S2263

100. Akos015965305

101. Tox21_111509_1

102. Db11217

103. Ks-5252

104. Sdccgmls-0066538.p001

105. P-hydroxyphenyl Beta -d-glucopyranoside

106. Smp1_000028

107. Ncgc00166076-02

108. Ncgc00166076-03

109. Ncgc00166076-04

110. Ncgc00166076-07

111. Ncgc00166076-09

112. Ncgc00255705-01

113. Ac-20183

114. Beta -d-glucopyranoside, 4-hydroxyphenyl

115. Beta-d-glucopyranoside, 4-hydroxyphenyl-

116. I(2)-d-glucopyranoside, 4-hydroxyphenyl

117. Smr001233417

118. A0522

119. Ab00443586

120. Hydroquinone-.beta.-d-glucopyranoside

121. N1714

122. Sw199492-2

123. C06186

124. 4-hydroxyphenyl B-d-glucopyranoside, 9ci, 8ci

125. 497a767

126. A827849

127. Arbutin, Primary Pharmaceutical Reference Standard

128. Q416446

129. Sr-05000002157-2

130. Sr-05000002157-4

131. Alpha-arbutin; 4-hydroquinone-alpha-d-glucopyranoside

132. Arbutin, European Pharmacopoeia (ep) Reference Standard

133. 4e19b706-2013-4401-a1fc-a154dadf42b4

134. (2s,3r,4s,5s,6r)-2-(4-hydroxyphenoxy)-6-methylol-tetrahydropyran-3,4,5-triol

135. 7oq

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₆O₇
Molecular Weight	272.25 g/mol
XLogP3	-0.7
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	3
Exact Mass	272.08960285 g/mol
Monoisotopic Mass	272.08960285 g/mol
Topological Polar Surface Area	120 Å²
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

4 Drug and Medication Information

4.1 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.

PMID:18996230 Nawarak J et al; Biochim Biophys Acta Oct 18 (Epub ahead of print) (2008)

4.2 Drug Indication

Indicated for over-the-counter use for epidermal hyperpigmentation in various skin conditions, such as melasma, freckles, and senile lentigines.

5 Pharmacology and Biochemistry

5.1 Pharmacology

At non-toxic concentrations, arbutin inhibited the activity of tyrosinase in cultured human keratinocytes, while having minimal effect on the expression of tyrosinase mRNA or the synthesis of the enzyme. -Arbutin produced a concentration-dependent inhibition of melanin synthesis of human melanoma cells, HMV-II. No inhibitory effect on HMV-II cell growth was seen at concentrations lower than 1.0 mM. At concentrations of 0.5 mM of arbutin, tyrosinase activity was reduced to 60% of that in non-treated cells. The addition of arbutin blocked and inhibited -MSH-stimulated melanogenesis in B16 melanoma cells, brownish guinea pig, and human skin tissue. In a pilot study of healthy male adults exposed to UV B irradiation, topical administration of arbutin inhibited UV-induced nuclear factor-kappaB activation in human keratinocytes. In mouse skin, arbutin counteracted oxidative stress induced by 12-O-tetradecanoylphorbol-13-acetate.

5.2 Absorption, Distribution and Excretion

Absorption

Arbutin was found to be extensively absorbed from the gastrointestinal tract where it is primarily converted to hydroquinone.

Route of Elimination

During the first 4 hours following ingestion of a single dose of 210 mg arbutin in healthy volunteers, 224.5 mol/L hydroquinone glucuronide and 182 mol/L of hydroquinone sulfate were recovered in the urine.

Volume of Distribution

No pharmacokinetic data available.

Clearance

No pharmacokinetic data available.

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).

PMID:12162475 Schindler G et al; J Clin Pharmacol 42 (8): 920-7 (2002)

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 (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.

PMID:15623110 Yang ZQ et al; Zhonghua Zheng Xing Wai Ke Za Zhi 20 (5): 369-71 (2004)

5.3 Metabolism/Metabolites

Arbutin is readily susceptible to hydrolysis in dilute acids to yield D-glucose and hydroquinone. It is expected that orally administered arbutin is easily hydrolyzed to free hydroquinone molecules by stomach acid. Hydroquinone is further metabolized into the main metabolites, hydroquinone glucuronide and hydroquinone sulfate.

5.4 Biological Half-Life

No pharmacokinetic data available.

5.5 Mechanism of Action

Arbutin is a hydroquinone glycoside, however the hydroquinone moiety is not solely responsible for the de-pigmentating actions of arbutin. It acts as a competitive inhibitor of tyrosinase enzyme by acting on the L-tyrosine binding site to suppress melanogenesis and mediate its de-pigmenting actions on human skin. Tyrosinase is an enzyme involved in the regulation of rate-limiting steps during the synthesis of melanin; it regulates the conversion of L-tyrosine into L-dopa, and subsequent conversion of L-dopa to L-dopaquinone. Via inhibition of tyrosinase activity in a concentration-dependent manner, arbutin attenuates the production of melanin in melanocytes. While most studies suggest that arbutin has negligible effect on the tyrosinase mRNA expression, a study assessing the effect of arbutin on melanocyte differentiation inducement system using ES cells propose that arbutin may also downregulate the expression of tyrosinase in addition to its inhibitory action on the enzyme. The contradictory findings across studies may be due to previous studies using terminally-differentiated melanocytes and melanoma cells.

...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.

PMID:10403123 Jin YH et al; Arch Pharm Res 22 (3): 232-6 (1999)

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DEVSHI"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1723746600,"product":"SINO WHITE A-ABT (INCL ALPHA ARBUTIN) (NOT INTENDED FOR USEIN FOOD PRODUCTS ; NOT FOR HUMAN CONSUMPTION)","address":"207,THE SUMMIT PREMISES CO-OP SOC","city":"MUMBAI,MAHARASHTRA","supplier":"SUNFINE GLOBAL CO ","supplierCountry":"REPUBLIC OF KOREA","foreign_port":"BUSAN(KOREA)","customer":"OC SPECIALITIES CHEMICALS ","customerCountry":"INDIA","quantity":"75.00","actualQuantity":"75","unit":"KGS","unitRateFc":"66.5","totalValueFC":"5208.4","currency":"USD","unitRateINR":"5766.9","date":"16-Aug-2024","totalValueINR":"432515.79","totalValueInUsd":"5208.4","indian_port":"JNPT","hs_no":"29389090","bill_no":"5073138","productDescription":"API","marketType":"","country":"REPUBLIC OF KOREA","selfForZScoreResived":"Pharma Grade","supplierPort":"BUSAN(KOREA)","supplierAddress":"3,SANGJEONG 1-GIL OSONG-EUPHEUNGDEOK-GU CHEONGJU-SI,CHUNGCHEONGBUK-DO KR","customerAddress":"207,THE SUMMIT PREMISES CO-OP SOC"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1724610600,"product":"ALPHA ARBUTIN (4-HYDROXYPHENYLA-D-GLUCOPYRANOSIDE (RAWMATERIAL FOR COSMETIC USE)","address":"706-707, QUANTUM TOWER, RAMBAGH LANE","city":"MALAD WEST","supplier":"HANGZHOU LINGEBA TECHNOLOGY ","supplierCountry":"CHINA","foreign_port":"SHANGHAI","customer":"BARENTZ INDIA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"200.00","actualQuantity":"200","unit":"KGS","unitRateFc":"350","totalValueFC":"10111.4","currency":"CNY","unitRateINR":"4198.4","date":"26-Aug-2024","totalValueINR":"839678.25","totalValueInUsd":"10111.4","indian_port":"JNPT","hs_no":"29389090","bill_no":"5262542","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"SHANGHAI","supplierAddress":"A1-3-633 XIXI CENTER,WENYI WEST ROAXIHU DISTRICT, HANGZHOU,ZHEJIANG,P.SDNF CN","customerAddress":"706-707, QUANTUM TOWER, RAMBAGH LANE"}]

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42 Topical

25 Thickeners and Stabilizers

23 Solubilizers

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12 Surfactant & Foaming Agents

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8 Empty Capsules

8 Direct Compression

6 Granulation

5 Taste Masking

4 Rheology Modifiers

3 API Stability Enhancers

1 Chewable & Orodispersible Aids

1 Coloring Agents

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