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
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
| Molecular Formula | C12H16O7 |
| Molecular Weight | 272.2512 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P14679 Gene ID: 7299.0 Gene Symbol: TYR Target Organism: Homo sapiens (Human) |
2.29 mM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseAlpha-arbutin is regarded as safe for consumer skin care products in concentrations up to 2% for face creams, and 0.5% for body lotions. |
Doses
| Dose | Population | Adverse events |
|---|---|---|
7 % 1 times / day steady-state, topical Studied dose Dose: 7 %, 1 times / day Route: topical Route: steady-state Dose: 7 %, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: |
Other AEs: hypopigmentation... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| hypopigmentation | 3 patients | 7 % 1 times / day steady-state, topical Studied dose Dose: 7 %, 1 times / day Route: topical Route: steady-state Dose: 7 %, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Opinion of the Scientific Committee on Consumer safety (SCCS)--Opinion on the safety of the use of α-arbutin in cosmetic products. | 2016-02 |
|
| Beta-cyclodextrin conjugates with glucose moieties designed as drug carriers: their syntheses, evaluations using concanavalin A and doxorubicin, and structural analyses by NMR spectroscopy. | 2008-05 |
|
| Arbutin blocks defects in the ripple phase of DMPC bilayers by changing carbonyl organization. | 2007-05 |
|
| Modulating effects of a novel skin-lightening agent, alpha-lipoic acid derivative, on melanin production by the formation of DOPA conjugate products. | 2007-03-01 |
|
| Synthesis of hydroquinone-alpha-glucoside by alpha-glucosidase from baker's yeast. | 2005-04 |
|
| Syntheses of arbutin-alpha-glycosides and a comparison of their inhibitory effects with those of alpha-arbutin and arbutin on human tyrosinase. | 2003-07 |
|
| The effect of arbutin on membrane integrity during drying is mediated by stabilization of the lamellar phase in the presence of nonbilayer-forming lipids. | 2001-05 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26646661
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15056856
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.
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
72VUP07IT5
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Validated (UNII)
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