U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C12H16O7
Molecular Weight 272.2512
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARBUTIN

SMILES

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

InChI

InChIKey=BJRNKVDFDLYUGJ-RMPHRYRLSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment: http://www.fda.gov/ohrms/dockets/dockets/95s0316/rpt0071_01.pdf; https://www.ncbi.nlm.nih.gov/pubmed/2179048; https://www.ncbi.nlm.nih.gov/pubmed/27129306

Arbutin, the beta-D-glucopyranoside of hydroquinone, is a skin whitening cosmetic ingredient. Compared with hydroquinone, arbutin is a less potent skin hyperpigmentation agent, but less toxic. Arbutin is found in a number of edible berry-producing plants such as blueberry and cranberry, marjoram, and most pear species. Chinchircoma (Muticia acuminatai) that contains arbutin, has been traditionally used by South American populations internally the fresh juice is used for gastric ulcers and internal tumors; the water of boiled leaves and flowers for illness of the respiratory tract; for hearth disorders or pain. According to pharmacological results in vitro, liver protective effects as well as anti-inflammatory activity were proven. It can also be beneficial for asthma and other anaphylactic reactions. This plant is component of the lsula Rain’s botanical products (Peru): ‘I-Day Digestive Cleanse #2.Herbal Supplement approved by FDA. As a hyperpigmentation agent arbutin inhibits tyrosinase and thus prevents the formation of melanin.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P14679
Gene ID: 7299.0
Gene Symbol: TYR
Target Organism: Homo sapiens (Human)
0.04 mM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Alpha Arbutin Cream

Approved Use

Cream for skin lightening Alpha Arbutin ensures an even and lighter skin tone, reduces the degree of skin tanning after UV exposure, and it also helps to minimize the appearance of liver spots.
PubMed

PubMed

TitleDatePubMed
Mutagenicity of arbutin in mammalian cells after activation by human intestinal bacteria.
2006 Nov
Characterization of dimers of hydroquinone glucosides produced by peroxidase-catalyzed polymerization.
2007 Apr
Toxicogenomics of A375 human malignant melanoma cells treated with arbutin.
2007 Jan
Novel screening method for potential skin-whitening compounds by a luciferase reporter assay.
2010
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.
2011 Dec 15
Involvement of the p38 MAPK and ERK signaling pathway in the anti-melanogenic effect of methyl 3,5-dicaffeoyl quinate in B16F10 mouse melanoma cells.
2012 Aug 30
Patents

Sample Use Guides

For the first 2 weeks use twice a day on cleansed skin (morning and night) then resume to once a day there after
Route of Administration: Topical
In Vitro Use Guide
Effects of isolated from Salvia officinalis compounds on melanin biosynthesis and cell proliferation of B16 melanoma cells were studied using arbutin as a positive control at a concentration of 100 mg/ml. Cells were incubated for 48 h with a test compound. Arbutin showed 49.3% melanin content at a concentration of 100 ug/ml keeping cell viability at 86.5%.
Name Type Language
ARBUTIN
HSDB   INCI   MART.   MI   WHO-DD  
INCI  
Official Name English
ARBUTINUM [HPUS]
Common Name English
ARBUTIN [HSDB]
Common Name English
Arbutin [WHO-DD]
Common Name English
HYDROQUINONE GLUCOSE
Systematic Name English
ARBUTIN [MI]
Common Name English
HYDROQUINONE-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
ARBUTOSIDE
Common Name English
4-HYDROXYPHENYL-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
NSC-4036
Code English
ARBUTIN [MART.]
Common Name English
ARBUTIN [INCI]
Common Name English
URSIN
Common Name English
ARBUTINUM
HPUS  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C471
Created by admin on Fri Dec 15 15:20:32 GMT 2023 , Edited by admin on Fri Dec 15 15:20:32 GMT 2023
DSLD 1289 (Number of products:3)
Created by admin on Fri Dec 15 15:20:32 GMT 2023 , Edited by admin on Fri Dec 15 15:20:32 GMT 2023
Code System Code Type Description
DRUG BANK
DB11217
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PRIMARY
MERCK INDEX
m2033
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PRIMARY Merck Index
ECHA (EC/EINECS)
207-850-3
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HSDB
7661
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FDA UNII
C5INA23HXF
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CAS
497-76-7
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EVMPD
SUB33412
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DAILYMED
C5INA23HXF
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NCI_THESAURUS
C87429
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EPA CompTox
DTXSID7040152
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CHEBI
18305
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DRUG CENTRAL
4267
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SMS_ID
100000126183
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RXCUI
1367175
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PRIMARY RxNorm
NSC
4036
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PRIMARY
PUBCHEM
440936
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WIKIPEDIA
ARBUTIN
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