α-Arbutin | CAS#84380-01-8 | Tyrosinase inhibitor

MedKoo Cat#: 330210 | Name: α-Arbutin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Arbutin is a glycoside; a glycosylated hydroquinone extracted from the bearberry plant in the genus Arctostaphylos among many other medicinal plants, primarily in the family Ericaceae. Applied topically, it inhibits tyrosinase and thus prevents the formation of melanin. Arbutin is therefore used as a skin-lightening agent. Very tiny amounts of arbutin are found in wheat, pear skins, and some other foods. It is also found in Bergenia crassifolia. Arbutin was also produced by an in vitro culture of Schisandra chinensis. α-Arbutin Protects Against Parkinson's Disease-Associated Mitochondrial Dysfunction In Vitro and In Vivo.

Chemical Structure

α-Arbutin

CAS#84380-01-8

Theoretical Analysis

MedKoo Cat#: 330210

Name: α-Arbutin

CAS#: 84380-01-8

Chemical Formula: C12H16O7

Exact Mass: 272.0896

Molecular Weight: 272.25

Elemental Analysis: C, 52.94; H, 5.92; O, 41.14

Price and Availability

Size	Price	Availability
5g	USD 250.00	2 Weeks
10g	USD 350.00	2 Weeks
25g	USD 650.00	2 Weeks

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Synonym

α-Arbutin; 4-Hydroxyphenyl α-D-Glucopyranoside

IUPAC/Chemical Name

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)tetrahydro-2H-pyran-3,4,5-triol

InChi Key

BJRNKVDFDLYUGJ-ZIQFBCGOSA-N

InChi Code

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

SMILES Code

O[C@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)[C@H]1OC2=CC=C(O)C=C2

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Parkinson's disease (PD), the most common neurodegenerative movement disorder, is characterized by the progressive loss of dopaminergic neurons in substantia nigra. The underlying mechanisms of PD pathogenesis have not been fully illustrated and currently PD remains incurable. Accumulating evidences suggest that mitochondrial dysfunction plays pivotal role in the dopaminergic neuronal death. Therefore, discovery of novel and safe agent for rescuing mitochondrial dysfunction would benefit PD treatment.

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 272.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Ding Y, Kong D, Zhou T, Yang ND, Xin C, Xu J, Wang Q, Zhang H, Wu Q, Lu X, Lim K, Ma B, Zhang C, Li L, Huang W. α-Arbutin Protects Against Parkinson's Disease-Associated Mitochondrial Dysfunction In Vitro and In Vivo. Neuromolecular Med. 2019 Aug 10. doi: 10.1007/s12017-019-08562-6. [Epub ahead of print] PubMed PMID: 31401719. 2: Chunhakant S, Chaicharoenpong C. Antityrosinase, Antioxidant, and Cytotoxic Activities of Phytochemical Constituents from Manilkara zapota L. Bark. Molecules. 2019 Jul 31;24(15). pii: E2798. doi: 10.3390/molecules24152798. PubMed PMID: 31370334; PubMed Central PMCID: PMC6696208. 3: Zhu L, Xu M, Lu C, Chen L, Xu A, Fang J, Chen H, Lu Y, Fan Y, Chen X. Optimization of whole-cell biotransformation for scale-up production of α-arbutin from hydroquinone by the use of recombinant Escherichia coli. AMB Express. 2019 Jun 28;9(1):94. doi: 10.1186/s13568-019-0820-7. PubMed PMID: 31254161; PubMed Central PMCID: PMC6598918. 4: Zhu L, Jiang D, Zhou Y, Lu Y, Fan Y, Chen X. Batch-feeding whole-cell catalytic synthesis of α-arbutin by amylosucrase from Xanthomonas campestris. J Ind Microbiol Biotechnol. 2019 Jun;46(6):759-767. doi: 10.1007/s10295-019-02143-z. Epub 2019 Mar 1. PubMed PMID: 30820723. 5: Zhu X, Tian Y, Zhang W, Zhang T, Guang C, Mu W. Recent progress on biological production of α-arbutin. Appl Microbiol Biotechnol. 2018 Oct;102(19):8145-8152. doi: 10.1007/s00253-018-9241-9. Epub 2018 Jul 21. Review. PubMed PMID: 30032433. 6: Ayumi NS, Sahudin S, Hussain Z, Hussain M, Samah NHA. Polymeric nanoparticles for topical delivery of alpha and beta arbutin: preparation and characterization. Drug Deliv Transl Res. 2019 Apr;9(2):482-496. doi: 10.1007/s13346-018-0508-6. PubMed PMID: 29569027. 7: Liao AH, Ma WC, Wang CH, Yeh MK. Penetration depth, concentration and efficiency of transdermal α-arbutin delivery after ultrasound treatment with albumin-shelled microbubbles in mice. Drug Deliv. 2016 Sep;23(7):2173-2182. Epub 2014 Aug 22. PubMed PMID: 25148541. 8: Wei M, Ren Y, Liu C, Liu R, Zhang P, Wei Y, Xu T, Wang F, Tan T, Liu C. Fermentation scale up for α-arbutin production by Xanthomonas BT-112. J Biotechnol. 2016 Sep 10;233:1-5. doi: 10.1016/j.jbiotec.2016.05.022. Epub 2016 May 18. PubMed PMID: 27208754. 9: Schlessinger J, Saxena S, Mohr S. Assessment of a Novel Anti-Aging Hand Cream. J Drugs Dermatol. 2016 Apr;15(4):496-503. PubMed PMID: 27050706. 10: Sccs, Degen GH. Opinion of the Scientific Committee on Consumer safety (SCCS)--Opinion on the safety of the use of α-arbutin in cosmetic products. Regul Toxicol Pharmacol. 2016 Feb;74:75-6. doi: 10.1016/j.yrtph.2015.11.008. Epub 2015 Dec 2. PubMed PMID: 26646661. 11: Avonto C, Wang YH, Avula B, Wang M, Rua D, Khan IA. Comparative studies on the chemical and enzymatic stability of alpha- and beta-arbutin. Int J Cosmet Sci. 2016 Apr;38(2):187-93. doi: 10.1111/ics.12275. Epub 2015 Oct 7. PubMed PMID: 26352830. 12: Wang YH, Avonto C, Avula B, Wang M, Rua D, Khan IA. Quantitative Determination of α-Arbutin, β-Arbutin, Kojic Acid, Nicotinamide, Hydroquinone, Resorcinol, 4-Methoxyphenol, 4-Ethoxyphenol, and Ascorbic Acid from Skin Whitening Products by HPLC-UV. J AOAC Int. 2015 Jan-Feb;98(1):5-12. doi: 10.5740/jaoacint.14-123. PubMed PMID: 25857872. 13: Qin L, Wu Y, Liu Y, Chen Y, Zhang P. Dual effects of alpha-arbutin on monophenolase and diphenolase activities of mushroom tyrosinase. PLoS One. 2014 Oct 10;9(10):e109398. doi: 10.1371/journal.pone.0109398. eCollection 2014. PubMed PMID: 25303458; PubMed Central PMCID: PMC4193772. 14: Song NY, Cho JG, Im D, Lee DY, Wu Q, Seo WD, Kang HC, Lee YH, Baek NI. Triterpenoids from Fragaria ananassa calyx and their inhibitory effects on melanogenesis in B16-F10 mouse melanoma cells. Nat Prod Res. 2013;27(23):2219-23. doi: 10.1080/14786419.2013.805330. Epub 2013 Jun 18. PubMed PMID: 23772756. 15: Liu C, Zhang P, Zhang S, Xu T, Wang F, Deng L. Feeding strategies for the enhanced production of α-arbutin in the fed-batch fermentation of Xanthomonas maltophilia BT-112. Bioprocess Biosyst Eng. 2014 Feb;37(2):325-9. doi: 10.1007/s00449-013-0980-9. Epub 2013 May 31. PubMed PMID: 23722821. 16: Wan Y, Ma J, Xu R, He A, Jiang M, Chen K, Jiang Y. [Properties of sucrose phosphorylase from recombinant Escherichia coli and enzymatic synthesis of alpha-arbutin]. Sheng Wu Gong Cheng Xue Bao. 2012 Dec;28(12):1450-9. Chinese. PubMed PMID: 23593869. 17: Liu C, Zhang P, Liu L, Xu T, Tan T, Wang F, Deng L. Isolation of α-arbutin from Xanthomonas CGMCC 1243 fermentation broth by macroporous resin adsorption chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Apr 15;925:104-9. doi: 10.1016/j.jchromb.2013.01.013. Epub 2013 Jan 24. PubMed PMID: 23542677. 18: Liu CQ, Deng L, Zhang P, Zhang SR, Liu L, Xu T, Wang F, Tan TW. Screening of high α-arbutin producing strains and production of α-arbutin by fermentation. World J Microbiol Biotechnol. 2013 Aug;29(8):1391-8. doi: 10.1007/s11274-013-1302-8. Epub 2013 Mar 1. PubMed PMID: 23456857. 19: Seo DH, Jung JH, Lee JE, Jeon EJ, Kim W, Park CS. Biotechnological production of arbutins (α- and β-arbutins), skin-lightening agents, and their derivatives. Appl Microbiol Biotechnol. 2012 Sep;95(6):1417-25. doi: 10.1007/s00253-012-4297-4. Epub 2012 Jul 29. Review. PubMed PMID: 22843425. 20: Seo DH, Jung JH, Ha SJ, Cho HK, Jung DH, Kim TJ, Baek NI, Yoo SH, Park CS. High-yield enzymatic bioconversion of hydroquinone to α-arbutin, a powerful skin lightening agent, by amylosucrase. Appl Microbiol Biotechnol. 2012 Jun;94(5):1189-97. doi: 10.1007/s00253-012-3905-7. PubMed PMID: 22314516.