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MedKoo Cat#: 540024 | Name: Arbutin
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Description:

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

Arbutin is PLA2 and tyrosinase inhibitor found in Bergenia and Arctostaphylos used in skin whitening products. In drecreases melanin production.

Chemical Structure

Arbutin
CAS#497-76-7

Theoretical Analysis

MedKoo Cat#: 540024

Name: Arbutin

CAS#: 497-76-7

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 Quantity
10g USD 250.00 2 Weeks
25g USD 450.00 2 Weeks
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Related CAS #
No Data
Synonym
Arbutoside; Arbutyne; BRN 0089673; BRN0089673; BRN-0089673; CCRIS 9273; CCRIS-9273; CCRIS9273; HSDB 7661; HSDB-7661; HSDB7661; NSC 4036; NSC-4036; NSC4036; Ursin; Uvasol; Arbutin; β-Arbutin
IUPAC/Chemical Name
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)tetrahydro-2H-pyran-3,4,5-triol
InChi Key
BJRNKVDFDLYUGJ-RMPHRYRLSA-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
>2 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

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.

Recalculate based on batch purity %
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: Tai A, Ohno A, Ito H. Isolation and Characterization of the 2,2'-Azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) Radical Cation-Scavenging Reaction Products of Arbutin. J Agric Food Chem. 2016 Sep 28;64(38):7285-90. doi: 10.1021/acs.jafc.6b02847. Epub 2016 Sep 16. PubMed PMID: 27607833. 2: 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. 3: 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. 4: Liang K, Xu K, Bessarab D, Obaje J, Xu C. Arbutin encapsulated micelles improved transdermal delivery and suppression of cellular melanin production. BMC Res Notes. 2016 Apr 30;9:254. doi: 10.1186/s13104-016-2047-x. PubMed PMID: 27129306; PubMed Central PMCID: PMC4851826. 5: Jeon JS, Kim BH, Lee SH, Kwon HJ, Bae HJ, Kim SK, Park JA, Shim JH, Abd El-Aty AM, Shin HC. Simultaneous determination of arbutin and its decomposed product hydroquinone in whitening creams using high-performance liquid chromatography with photodiode array detection: Effect of temperature and pH on decomposition. Int J Cosmet Sci. 2015 Dec;37(6):567-73. doi: 10.1111/ics.12228. Epub 2015 May 7. PubMed PMID: 25857400. 6: Qi WY, Ou N, Wu XD, Xu HM. New arbutin derivatives from the leaves of Heliciopsis lobata with cytotoxicity. Chin J Nat Med. 2016 Oct;14(10):789-793. doi: 10.1016/S1875-5364(16)30094-2. Epub 2016 Oct 31. PubMed PMID: 28236409. 7: 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. 8: Kuźniak E, Wielanek M, Chwatko G, Głowacki R, Libik-Konieczny M, Piątek M, Gajewska E, Skłodowska M. Salicylic acid and cysteine contribute to arbutin-induced alleviation of angular leaf spot disease development in cucumber. J Plant Physiol. 2015 Jun 1;181:9-13. doi: 10.1016/j.jplph.2015.03.017. Epub 2015 Apr 17. PubMed PMID: 25955697. 9: Jurica K, Karačonji IB, Šegan S, Opsenica DM, Kremer D. Quantitative analysis of arbutin and hydroquinone in strawberry tree (Arbutus unedo L., Ericaceae) leaves by gas chromatography-mass spectrometry. Arh Hig Rada Toksikol. 2015 Sep 1;66(3):197-202. doi: 10.1515/aiht-2015-66-2696. PubMed PMID: 26444340. 10: Shams A, Khan IU, Iqbal H. Analysis of salicylic acid, arbutin and corticosteroids in skin whitening creams available in Pakistan using chromatographic techniques. Int J Cosmet Sci. 2016 Aug;38(4):421-8. doi: 10.1111/ics.12310. Epub 2016 Apr 5. PubMed PMID: 26855207. 11: 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. 12: Morag M, Nawrot J, Siatkowski I, Adamski Z, Fedorowicz T, Dawid-Pac R, Urbanska M, Nowak G. A double-blind, placebo-controlled randomized trial of Serratulae quinquefoliae folium, a new source of β-arbutin, in selected skin hyperpigmentations. J Cosmet Dermatol. 2015 Sep;14(3):185-90. doi: 10.1111/jocd.12147. Epub 2015 Jun 28. PubMed PMID: 26119285. 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: SCCS., Degen GH. Opinion of the Scientific Committee on Consumer Safety (SCCS)--Opinion on the safety of the use of β-arbutin in cosmetic products. Regul Toxicol Pharmacol. 2015 Dec;73(3):866-7. doi: 10.1016/j.yrtph.2015.10.008. Epub 2015 Oct 19. PubMed PMID: 26482403. 15: Wu LH, Li P, Zhao QL, Piao JL, Jiao YF, Kadowaki M, Kondo T. Arbutin, an intracellular hydroxyl radical scavenger, protects radiation-induced apoptosis in human lymphoma U937 cells. Apoptosis. 2014 Nov;19(11):1654-63. doi: 10.1007/s10495-014-1032-x. PubMed PMID: 25187044. 16: 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. 17: 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. 18: 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. 19: Tada M, Kohno M, Niwano Y. Alleviation effect of arbutin on oxidative stress generated through tyrosinase reaction with L-tyrosine and L-DOPA. BMC Biochem. 2014 Oct 9;15:23. doi: 10.1186/1471-2091-15-23. PubMed PMID: 25297374; PubMed Central PMCID: PMC4195341. 20: Sasaki C, Ichitani M, Kunimoto KK, Asada C, Nakamura Y. Extraction of arbutin and its comparative content in branches, leaves, stems, and fruits of Japanese pear Pyrus pyrifolia cv. Kousui. Biosci Biotechnol Biochem. 2014;78(5):874-7. doi: 10.1080/09168451.2014.893185. Epub 2014 May 9. PubMed PMID: 25035992.

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