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Revision as of 10:32, 12 November 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: StdInChI StdInChIKey.← Previous edit Latest revision as of 16:20, 9 December 2024 edit undoCitation bot (talk | contribs)Bots5,391,923 edits Add: bibcode, authors 1-1. Removed URL that duplicated identifier. Removed parameters. Some additions/deletions were parameter name changes. | Use this bot. Report bugs. | Suggested by Dominic3203 | Linked from User:Marbletan/sandbox | #UCB_webform_linked 273/2664 
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{{short description|Glycoside}}
{{Distinguish|text=the structurally similar stereoisomer ]}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 396118682
| Watchedfields = changed
| ImageFile = Arbutin structure.svg
| verifiedrevid = 396293096
| ImageSize = 200px
| ImageFile = Arbutin structure.svg
| IUPACName = (''2R,3S,4S,5R,6S'')-2-Hydroxymethyl-6- (4-hydroxyphenoxy)oxane-3,4,5-triol
| OtherNames = Arbutoside<br>Hydroquinone β-D-glucopyranoside | IUPACName = 4-Hydroxyphenyl-β-{{sm|d}}-glucopyranoside
| SystematicName = (2''R'',3''S'',4''S'',5''R'',6''S'')-2-(Hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
| Section1 = {{Chembox Identifiers
| OtherNames = {{Unbulleted list
| Abbreviations =
|''beta''-Arbutin
|β-Arbutin
|Arbutoside
|Hydroquinone β-{{sm|d}}-glucopyranoside
|4-Hydroxyphenyl β-{{sm|d}}-gluco-hexopyranoside
}}
| Section1 = {{Chembox Identifiers
| Abbreviations =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 389765 | ChemSpiderID = 389765
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 232202
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = C5INA23HXF | UNII = C5INA23HXF
| InChIKey = BJRNKVDFDLYUGJ-RMPHRYRLBW | InChIKey = BJRNKVDFDLYUGJ-RMPHRYRLBW
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BJRNKVDFDLYUGJ-RMPHRYRLSA-N | StdInChIKey = BJRNKVDFDLYUGJ-RMPHRYRLSA-N
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 497-76-7 | CASNo = 497-76-7
| EINECS = | EINECS = 207-850-3
| PubChem = 440936 | PubChem = 346
| Beilstein = 89673
| SMILES = c1cc(ccc1O)O2((((O2)CO)O)O)O
| SMILES = C1=CC(=CC=C1O)O2((((O2)CO)O)O)O
| 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
| RTECS = | RTECS = CE8663000
| MeSHName = | MeSHName = Arbutin
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI =
| KEGG = | ChEBI = 18305
| KEGG_Ref = {{keggcite|correct|kegg}}
| ATCCode_prefix =
| KEGG = C06186
| DrugBank = DB11217
}}
| Section2 = {{Chembox Properties
| Properties_ref = <ref name="Sccs Degen 2015 pp. 866–867">{{cite journal | author=Sccs | last2=Degen | first2=Gisela H. | title=Opinion of the Scientific Committee on Consumer Safety (SCCS) – Opinion on the safety of the use of β-arbutin in cosmetic products | journal=Regulatory Toxicology and Pharmacology | volume=73 | issue=3 | date=2015 | doi=10.1016/j.yrtph.2015.10.008 | pages=866–867}}</ref>
| C=12 | H=16 | O=7
| MolarMass = 272.25
| Appearance = Colorless to white solid powder
| MeltingPtC = 197–201
| BoilingPtC =
| Solubility = 5.0 g/100 mL
| Solubility1 = soluble
| Solvent1 = ethanol
| SolubleOther = slightly soluble in ], ] and ]
| LogP = –1.35
| VaporPressure = 2.3{{x10^|-12}}{{nbsp}}mm Hg (25 °C)
| HenryConstant =
| LambdaMax = 285 nm<ref name="“:0">{{Cite web |date=2023-02-01 |title=SCCS (Scientific Committee on Consumer Safety), Opinion on the safety of alpha- (CAS No. 84380-018, EC No. 617-561-8) and beta-arbutin (CAS No. 497-76-7, EC No. 207-8503) in cosmetic products, preliminary version of 15-16 March 2022, final version of 31 January 2023, SCCS/1642/22 |url=https://health.ec.europa.eu/document/download/66cdc38f-68e7-4e47-b06a-7ba73b027fb6_en?filename=sccs_o_264.pdf |access-date=2023-03-07 |website=]}}</ref>
| AtmosphericOHRateConstant =
| pKa = 10.10
}}
| Section3 = {{Chembox Pharmacology
| Pharmacology_ref =
| ATCCode_prefix = D11
| ATCCode_suffix = | ATCCode_suffix =
| ATC_Supplemental =}} | ATC_Supplemental =
| ATCvet =
| Section2 = {{Chembox Properties
| Drug_class =
| Formula = C<sub>12</sub>H<sub>16</sub>O<sub>7</sub>
| Licence_EU =
| MolarMass = 272.25 g/mol
| Appearance = | INN =
| Density = | INN_EMA =
| MeltingPtC = 199.5 | Licence_US =
| Melting_notes = | Legal_status =
| BoilingPt = | Legal_AU =
| Boiling_notes = | Legal_AU_comment =
| Solubility = | Legal_BR =
| SolubleOther = | Legal_BR_comment =
| Solvent = | Legal_CA =
| pKa = | Legal_CA_comment =
| pKb = }} | Legal_NZ =
| Legal_NZ_comment =
| Section7 = {{Chembox Hazards
| EUClass = | Legal_UK =
| EUIndex = | Legal_UK_comment =
| Legal_US = Not FDA approved
| Legal_US_comment =
| Legal_EU = Unscheduled
| Legal_EU_comment =
| Legal_UN =
| Legal_UN_comment =
| Pregnancy_category =
| Pregnancy_AU =
| Pregnancy_AU_comment =
| Dependence_liability =
| AdminRoutes = ]
| Bioavail = 0.53% ]<ref name=":0"/>
| ProteinBound =
| Metabolism =
| Metabolites =
| OnsetOfAction =
| HalfLife =
| DurationOfAction =
| Excretion =
}}
| Section7 = {{Chembox Hazards
| Hazards_ref = <ref name="Sccs Degen 2015 pp. 866–867"/>
| GHS_ref =
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|}}
| MainHazards = | MainHazards =
| IngestionHazard = Low level of toxicity
| NFPA-H =
| NFPA-F = | InhalationHazard =
| EyeHazard = Irritation
| NFPA-R =
| SkinHazard = Irritation
| NFPA-O =
| RPhrases = | NFPA-H = 0
| SPhrases = | NFPA-F = 1
| RSPhrases = | NFPA-I = 0
| FlashPt = | NFPA-S =
| Autoignition = | NFPA_ref =
| FlashPt =
| FlashPtC =
| FlashPt_notes =
| FlashPt_ref =
| AutoignitionPt =
| AutoignitionPtC =
| AutoignitionPt_ref=
| AutoignitionPt_notes=
| ExploLimits = | ExploLimits =
| PEL = }} | TLV =
| TLV-TWA =
| TLV-STEL =
| TLV-C =
| LD50 = 9.8 g/kg (mouse, oral), 8.7 g/kg (rat, oral), 978 mg/kg (rat, mouse, dermal) (maximum practically applicable dosage)<ref name="Sccs Degen 2015 pp. 866–867"/>
| LDLo =
| LC50 =
| LCLo =
| PEL =
| REL =
| IDLH =
| NIOSH_id =
| NIOSH_ref =
<!-- (data page) -->
| ExternalSDS =
}}
| Section8 = {{Chembox Related
| OtherCompounds = {{ubl|
*]
*]
}}
}}
}} }}


'''β-Arbutin''', also known by its ] (INCI) name, '''arbutin''', is a ] derivative of ]. β-Arbutin is naturally present in the leaves and bark of a variety of plants, notably the bearberry plant, '']''. Utilized as a biosynthetic active ingredient in ] treatments for ], β-arbutin is aimed at addressing ] issues. Its mechanism of action involves inhibiting the activity of ], an essential enzyme for ] synthesis in the ], thereby leading to a reduction in hyperpigmentation. It is important to distinguish β-arbutin from its structurally similar ], ], which exhibits similar effects in clinical applications.<ref name=":0">{{Cite web |last=Scientific Committee on Consumer Safety (SCCS) |author-link=Scientific Committee on Consumer Safety |date=1 February 2023 |title=Opinion on the safety of alpha- (CAS No. 84380-018, EC No. 617-561-8) and beta-arbutin (CAS No. 497-76-7, EC No. 207-8503) in cosmetic products, preliminary version of 15–16 March 2022, final version of 31 January 2023, SCCS/1642/22 |url=https://health.ec.europa.eu/document/download/66cdc38f-68e7-4e47-b06a-7ba73b027fb6_en?filename=sccs_o_264.pdf |access-date=7 March 2024 |website=] |type=Expert Opinion}}</ref>
'''Arbutin''' also known as ] and ] is both an ] and a ]; a glycosylated ] extracted from ] plant in the genus ''Arctostaphylos''. It ] ] and thus prevents the formation of ]. Arbutin is therefore used as a skin-lightening agent. Arbutin is found in ], and is concentrated in ] skins. It is also found in '']''<ref></ref>.


== Skin Lightening Agent == == Properties ==
Arbutin is a compound where a ] molecule, specifically {{sm|d}}-glucose, is chemically bound to ]. In aqueous solutions, glucose can exist in one of three ] forms: α, β, or γ, with the β-] being the predominant form.<ref name=":1">{{Cite journal |last=Boo |first=Yong Chool |date=2021-07-15 |title=Arbutin as a Skin Depigmenting Agent with Antimelanogenic and Antioxidant Properties |journal=Antioxidants |language=en |volume=10 |issue=7 |pages=1129 |doi=10.3390/antiox10071129 |doi-access=free |issn=2076-3921 |pmc=8301119 |pmid=34356362}}</ref> The standard known form of arbutin, β-Arbutin, has a ] of C<sub>12</sub>H<sub>16</sub>O<sub>7</sub> and a ] of 272.25{{Nbsp}}]. Its stereoisomers, ] and ], share the same molecular formula and weight but are distinct in their atoms' ].<ref>{{Cite journal |last=Chemistry (IUPAC) |first=The International Union of Pure and Applied |title=IUPAC - stereoisomerism (S05983) |url=https://goldbook.iupac.org/terms/view/S05983 |access-date=2024-03-07 |website=goldbook.iupac.org|doi=10.1351/goldbook.S05983 |doi-access=free }}</ref>


β-Arbutin is soluble in water, presenting typically as a white powder that remains stable under standard storage conditions. It exhibits stability in both ethanol and water and demonstrates resistance to light exposure.<ref name=":2">{{Cite journal |last1=Migas |first1=Piotr |last2=Krauze-Baranowska |first2=Mirosława |date=2015-09-01 |title=The significance of arbutin and its derivatives in therapy and cosmetics |url=https://www.sciencedirect.com/science/article/pii/S1874390015001123 |journal=Phytochemistry Letters |volume=13 |pages=35–40 |doi=10.1016/j.phytol.2015.05.015 |bibcode=2015PChL...13...35M |issn=1874-3900}}</ref> When dissolved in water, β-arbutin may undergo ], converting to ], which can subsequently ] to ].<ref name=":2" />
Bearberry Extract is used in skin lightening treatments designed for for long term and regular use. An active agent in brands of skin lightening preparations like ], it is more expensive than traditional skin lightening ingredients like ], which is now banned in many countries.


== Occurrence and preparation ==
In vitro studies of human ] exposed to arbutin at concentrations below 300 μg/mL reported decreased tyrosinase activity and melanin content with little evidence of cytotoxicity.<ref></ref>
The compound is naturally occurring and can be extracted from several plant species. Traditionally extracted from the bearberry plant ('']''), it also occurs in high levels in plants in the families of ] and ].<ref>{{Cite journal |last1=Garcia-Jimenez |first1=Antonio |last2=Teruel-Puche |first2=Jose Antonio |last3=Berna |first3=Jose |last4=Rodriguez-Lopez |first4=José Neptuno |last5=Tudela |first5=Jose |last6=Garcia-Canovas |first6=Francisco |date=2017-05-11 |title=Action of tyrosinase on alpha and beta-arbutin: A kinetic study |journal=PLOS ONE |language=en |volume=12 |issue=5 |pages=e0177330 |doi=10.1371/journal.pone.0177330 |doi-access=free |issn=1932-6203 |pmc=5426667 |pmid=28493937|bibcode=2017PLoSO..1277330G }}</ref> Others include the ] (''Pyrus spp.''), and certain species of ]. It is also found in very small quantities in ''],'' ''] and ]''.<ref>{{cite journal|url=http://notulaebotanicae.ro/nbha/article/viewFile/3108/2947 |title=Natural Resources Containing Arbutin. Determination of Arbutin in the Leaves of Bergenia crassifolia (L.) Fritsch. acclimated in Romania |author1=Carmen Pop |author2=Laurian Vlase |author3=Mircea Tamas |journal=Not. Bot. Hort. Agrobot. Cluj |volume=37 |issue=1 |year=2009 |pages=129–132 |url-status=dead |archive-url=https://web.archive.org/web/20110823104032/http://notulaebotanicae.ro/nbha/article/viewFile/3108/2947 |archive-date=2011-08-23 }}</ref><ref>{{cite journal | pmid = 15895970 | title = |vauthors=Dusková J, Dusek J, Jahodár L, Poustka F | journal = Ceska Slov Farm. | volume = 54 | issue = 2 | year = 2005 | pages = 78–81}}</ref>


Synthetically, it can also be prepared from the reaction of ] and ] in the presence of an ].<ref>{{Cite journal |date=2007-03-20 |title=Hawley's Condensed Chemical Dictionary, 15th ed By Richard J. Lewis, Sr. John Wiley & Sons, Inc.: Hoboken, NJ. 2007. x + 1380 pp. $150.00. ISBN 978-0-471-76865-4. |url=http://dx.doi.org/10.1021/ja0769144 |journal=Journal of the American Chemical Society |volume=129 |issue=16 |pages=5296 |doi=10.1021/ja0769144 |bibcode=2007JAChS.129R5296. |issn=0002-7863}}</ref>


== Uses ==
The main application of β-arbutin is in the ], where it is incorporated into various skin care products, including creams, serums and lotions, aimed at ] tone and correcting ]. Its efficacy and safety profile make it a sought-after ingredient for products targeting ], ]s, ], and ].


== Risks == === Herbal medicine ===
For centuries, β-arbutin has been used in ], or herbal medicine.<ref name=":2" /> Extracted from the leaves of bearberry plants, it is used as a mixture with other herbal drugs as a treatment for ].<ref name=":2" />


== Mechanism of action ==
Arbutin is ] ],<ref>{{cite journal | author = O'Donoghue, J L | date = | year = 2006 | month = September | title = Hydroquinone and its analogues in dermatology – a risk-benefit viewpoint | journal = Journal of Cosmetic Dermatology | volume = 5 | issue = 3 | pages = 196–203 | doi = 10.1111/j.1473-2165.2006.00253.x
| pmid = 17177740 | url = | format = | accessdate = | quote = "The potential toxicity of HQ (hydroquinone) is dependent on the route of exposure" }}</ref> and may carry similar cancer risks,<ref>smartskincare.com </ref> although there are also claims that arbutin reduces cancer risk.<ref>Bowman, Lee. July 25, 2005. Scripps Howard News Service. </ref> The German Institute of Food Research in ] found that intestinal bacteria can transform arbutin into hydroquinone, which creates an environment favourable for ]. It is known that the body excretes 64-75% of arbutin in urine, and arbutin converted to hydroquinone has an antibacterial effect in the ], hence the use of bearberry in ], but it is not known why this substance plays a role in cancer development.
it also has an antiglycation activity


=== Regulation of melanin synthesis ===
== References ==
β-Arbutin acts as an ] of cellular ] by inactivating it.<ref name=":1" /> Tyrosinase is an enzyme needed in ] synthesis in the melanin producing cell of the ], the ]. By reducing the activity of tyrosinase, β-arbutin reduces the synthesis of melanin, leading to a lighter skin tone and the diminished appearance of hyperpigmentation. It is not as potent an inhibitor of tyrosinase as α-arbutin.<ref name=":2" />
{{reflist}}
Arom Jedsadayanmata, In Vitro Antiglycation Activity of Arbutin, Naresuan University Journal 2005; 13(2): 35-41


It has also been shown act as a ] for tyrosinase.<ref name=":1" /> Tyrosinase ] the ] of ], an ], to {{Sm|l}}-DOPA (levodopa) and the ] of {{Sm|d}}-DOPA to ] which is then further metabolised to ]. β-Arbutin is thought to have structural similarities to the substrate tyrosine, and this may inhibit the activity of tyrosinase.<ref name=":0" /><ref>{{Cite journal |last1=Zhu |first1=Wenyuan |last2=Gao |first2=Jie |date=April 2008 |title=The Use of Botanical Extracts as Topical Skin-Lightening Agents for the Improvement of Skin Pigmentation Disorders |journal=Journal of Investigative Dermatology Symposium Proceedings |volume=13 |issue=1 |pages=20–24 |doi=10.1038/jidsymp.2008.8 |issn=1087-0024|doi-access=free }}</ref>
==External links==


=== Decomposition into hydroquinone ===
]
Conflicting evidence shows that β-arbutin may also work by being ] into hydroquinone. If this occurs, the amount of hydroquinone created by decomposition would be small and its contribution to inhibiting the creation of melanin as small.<ref name=":1" /><!--*remove as this may be the reason why alpha-arbutin works and not beta-arbutin* The EU determined that the effects of arbutins on the skin could be attributed to their gradual ] and release of ], which is banned in the EU.<ref name=":0" />-->
]

]
== Safety and regulation ==
]
β-Arbutin is generally considered safe for ] application in cosmetic products. However, its usage concentrations in the European Union (EU) are restricted by the ] ] to 7% in facial creams, provided the contamination of hydroquinone remains below 1 ppm.<ref name=":0" />

=== Skin-lightening agent ===
Bearberry extract is used in skin lightening treatments designed for long term and regular use. An active agent in brands of skin lightening preparations, it is more expensive than traditional skin lightening ingredients like ], which is now banned in many countries. In vitro studies of human ] exposed to arbutin at concentrations below 300 μg/mL reported decreased tyrosinase activity and melanin content with little evidence of cytotoxicity.<ref> {{webarchive|url=https://web.archive.org/web/20100527233957/http://ntp.niehs.nih.gov/files/Arbutin.pdf|date=May 27, 2010}}, Supporting Nomination for Toxicological Evaluation by the National Toxicology Program</ref>

==== Risks ====
Arbutin is ] ],<ref>{{cite journal |author=O'Donoghue, J L |date=September 2006 |title=Hydroquinone and its analogues in dermatology – a risk-benefit viewpoint |journal=Journal of Cosmetic Dermatology |volume=5 |issue=3 |pages=196–203 |doi=10.1111/j.1473-2165.2006.00253.x |pmid=17177740 |s2cid=38707467 |quote="The potential toxicity of HQ (hydroquinone) is dependent on the route of exposure"}}</ref> and may carry similar cancer risks,<ref>{{Cite web|url=http://www.smartskincare.com/conditions/pigmentation/hyperpigmentation-treatments.html|title=Smart Skin Care: Treatment of hyperpigmentation problems / skin lightening|website=www.smartskincare.com}}</ref>{{Unreliable source?|date=August 2011}} although there are also claims that arbutin reduces cancer risk.<ref>Bowman, Lee. July 25, 2005. Scripps Howard News Service. {{webarchive|url=https://web.archive.org/web/20070928010949/http://www.knoxstudio.com/shns/story.cfm?pk=BITTERS-07-25-05&cat=AN|date=September 28, 2007}}</ref> The German Institute of Food Research in ] found that intestinal bacteria can transform arbutin into hydroquinone, which creates an environment favorable for ].<ref name="pmid16904805">{{cite journal |vauthors=Blaut M, Braune A, Wunderlich S, Sauer P, Schneider H, Glatt H |year=2006 |title=Mutagenicity of arbutin in mammalian cells after activation by human intestinal bacteria |journal=Food Chem. Toxicol. |volume=44 |issue=11 |pages=1940–7 |doi=10.1016/j.fct.2006.06.015 |pmid=16904805}}</ref>

==See also==
* ]
* ]

== References ==
{{reflist}}


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