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 ALPHA-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-ZIQFBCGOSA-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
Both alpha and beta arbutin are known derivatives of hydroquinone and used as depigmenting agents in cosmetic formulations. Alpha-Arbutin has been shown to inhibit melanin synthesis but not the growth of human melanoma cells. Alpha arbutin inhibits tyrosinase with Ki of 2.29 mM, however, Beta-arbutin has a Ki of 0.08 mM.

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Alpha-arbutin is regarded as safe for consumer skin care products in concentrations up to 2% for face creams, and 0.5% for body lotions.
PubMed

PubMed

TitleDatePubMed
Syntheses of arbutin-alpha-glycosides and a comparison of their inhibitory effects with those of alpha-arbutin and arbutin on human tyrosinase.
2003 Jul
Patents

Sample Use Guides

Alpha-arbutin is considered safe for consumer products in concentrations up to 2% in face creams, and up to 0.5% in body lotions.
Route of Administration: Topical
Human Malignant melanoma cells (HMV-II) were plated with 10 mL of medium in a 100 mm dish and incubated for 10 days. Cells were treated with various concentrations of alpha-arbutin which were included as a component of the growth media. The medium was refreshed on days 1, 4, and 7. Cell proliferation was determined by counting with a hemocytometer. Melanin was extracted from lysed cells and quantified by measuring absorbance at 470 nm. Cellular tyrosinase activity was assayed using L-DOPA as a substrate while monitoring absorbance at 475 nm for a 3 hour period. The cellular content of melanin was reduced by addition of alpha-arbutin in a dose-dependent manner. Alpha-arbutin did not inhibit cell viability at 1 mM, but a small reduction was noted at 2 mM. The cellular tyrosinase activity was reduced to 60% of control at a concentration of 0.5 mM alpha-arbutin.
Name Type Language
ALPHA-ARBUTIN
INCI   WHO-DD  
INCI  
Official Name English
.ALPHA.-ARBUTIN
Common Name English
ALPHA-ARBUTIN [INCI]
Common Name English
Alpha-arbutin [WHO-DD]
Common Name English
ORISTAR AAT
Brand Name English
4-HYDROXYPHENYL-.ALPHA.-D-GLUCOPYRANOSIDE
Common Name English
P-HYDROXYPHENYL-.ALPHA.-D-GLUCOPYRANOSIDE
Common Name English
ALPHA ARBUTIN
Common Name English
Code System Code Type Description
EVMPD
SUB185343
Created by admin on Sat Dec 16 20:10:49 GMT 2023 , Edited by admin on Sat Dec 16 20:10:49 GMT 2023
PRIMARY
CAS
84380-01-8
Created by admin on Sat Dec 16 20:10:49 GMT 2023 , Edited by admin on Sat Dec 16 20:10:49 GMT 2023
PRIMARY
FDA UNII
72VUP07IT5
Created by admin on Sat Dec 16 20:10:50 GMT 2023 , Edited by admin on Sat Dec 16 20:10:50 GMT 2023
PRIMARY
DAILYMED
72VUP07IT5
Created by admin on Sat Dec 16 20:10:50 GMT 2023 , Edited by admin on Sat Dec 16 20:10:50 GMT 2023
PRIMARY
DRUG BANK
DB14109
Created by admin on Sat Dec 16 20:10:50 GMT 2023 , Edited by admin on Sat Dec 16 20:10:50 GMT 2023
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SMS_ID
100000171735
Created by admin on Sat Dec 16 20:10:50 GMT 2023 , Edited by admin on Sat Dec 16 20:10:50 GMT 2023
PRIMARY
PUBCHEM
158637
Created by admin on Sat Dec 16 20:10:50 GMT 2023 , Edited by admin on Sat Dec 16 20:10:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID20233358
Created by admin on Sat Dec 16 20:10:50 GMT 2023 , Edited by admin on Sat Dec 16 20:10:50 GMT 2023
PRIMARY
RXCUI
1363429
Created by admin on Sat Dec 16 20:10:50 GMT 2023 , Edited by admin on Sat Dec 16 20:10:50 GMT 2023
PRIMARY RxNorm