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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

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

Description

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
0.04 mM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Alpha Arbutin Cream
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

In Vivo Use Guide
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%.
Substance Class Chemical
Created
by admin
on Tue Oct 22 05:42:37 UTC 2019
Edited
by admin
on Tue Oct 22 05:42:37 UTC 2019
Record UNII
C5INA23HXF
Record Status Validated (UNII)
Record Version
  • Download
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 Tue Oct 22 05:42:37 UTC 2019 , Edited by admin on Tue Oct 22 05:42:37 UTC 2019
Code System Code Type Description
MERCK INDEX
M2033
Created by admin on Tue Oct 22 05:42:37 UTC 2019 , Edited by admin on Tue Oct 22 05:42:37 UTC 2019
PRIMARY Merck Index
ECHA (EC/EINECS)
207-850-3
Created by admin on Tue Oct 22 05:42:37 UTC 2019 , Edited by admin on Tue Oct 22 05:42:37 UTC 2019
PRIMARY
HSDB
497-76-7
Created by admin on Tue Oct 22 05:42:37 UTC 2019 , Edited by admin on Tue Oct 22 05:42:37 UTC 2019
PRIMARY
CAS
497-76-7
Created by admin on Tue Oct 22 05:42:37 UTC 2019 , Edited by admin on Tue Oct 22 05:42:37 UTC 2019
PRIMARY
EVMPD
SUB33412
Created by admin on Tue Oct 22 05:42:37 UTC 2019 , Edited by admin on Tue Oct 22 05:42:37 UTC 2019
PRIMARY
NCI_THESAURUS
C87429
Created by admin on Tue Oct 22 05:42:37 UTC 2019 , Edited by admin on Tue Oct 22 05:42:37 UTC 2019
PRIMARY
EPA CompTox
497-76-7
Created by admin on Tue Oct 22 05:42:37 UTC 2019 , Edited by admin on Tue Oct 22 05:42:37 UTC 2019
PRIMARY
RXCUI
1367175
Created by admin on Tue Oct 22 05:42:37 UTC 2019 , Edited by admin on Tue Oct 22 05:42:37 UTC 2019
PRIMARY RxNorm
PUBCHEM
440936
Created by admin on Tue Oct 22 05:42:37 UTC 2019 , Edited by admin on Tue Oct 22 05:42:37 UTC 2019
PRIMARY
WIKIPEDIA
ARBUTIN
Created by admin on Tue Oct 22 05:42:37 UTC 2019 , Edited by admin on Tue Oct 22 05:42:37 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (HPLC)
Related Record Type Details
METABOLITE -> PARENT
Unit: mg (calculated as arbutin); Urinary elimination profiles of arbutin metabolites (150mg arbutin in about 150mL aqueous bearberry leaf extract oral q.i.d., n=3, 16-24hr urine)
IN-VIVO
URINE
METABOLITE -> PARENT
Unit: mg (calculated as arbutin); 150mg arbutin in about 150mL aqueous bearberry leaf extract, q.i.d.; 0-24hr urine; n=3
IN-VIVO
URINE
METABOLITE -> PARENT
Amount excreted in urine within the 36-hour study period, 945mg bearberry leaf extract (corresponding to 210mg arbutin, in two film coated tabs) single oral administration, n=16 (8 female, 8 male), 0-36hr urine
IN-VIVO
URINE
METABOLITE -> PARENT
Amount excreted in urine within the 36-hour period, 945mg bearberry leaf dry extract (210mg arbutin equivalent, in aqueous solution) single oral administration, n=16 (8 female, 8 male)
IN-VIVO
URINE
METABOLITE -> PARENT
Unit: mg; Amount excreted in urine within 36-hr study period, Bearberry leaves dry extract(BLDE) 945mg single oral administration(210mg arbutin correspondence, in 2 film coated tabs, each contained 472.5mg BLDE or 105mg arbutin), n=16 (8 female & 8 male)
IN-VIVO
URINE
METABOLITE -> PARENT
945mg bear berry leaf extract (w/210mg arbutin) single oral administration, 0-4hr urine, n=1
IN-VIVO
URINE
METABOLITE -> PARENT
Unit: mg; Amount excreted in urine within 36-hr study period, Bearberry leaves dry extract(BLDE) 945mg single oral administration(210mg arbutin correspondence, aqueous solution), n=16 (8 female & 8 male)
IN-VIVO
URINE
METABOLITE -> PARENT
Amount excreted in urine within the 36-hour period, 945mg bearberry leaf dry extract (210mg arbutin equivalent, in two film coated tabs) single oral administration, n=16 (8 female, 8 male)
IN-VIVO
URINE
METABOLITE -> PARENT
Unit: mg calculated as arbutin; Urinary elimination of arbutin metabolites (16-24hr urine, n=3, 150mg arubutin in about 150mL aqueous bearberry leaf extract, q.i.d.)
IN-VIVO
URINE
METABOLITE -> PARENT
Amount excreted in urine within the 36-hour study period, 945mg bearberry leaf extract (corresponding to 210mg arbutin, in aqueous solution) single oral administration, n=16 (8 female, 8 male), 0-36hr urine
IN-VIVO
URINE
Related Record Type Details
ACTIVE MOIETY