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. |
PubMed
Title | Date | PubMed |
---|---|---|
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 May |
|
Syntheses of arbutin-alpha-glycosides and a comparison of their inhibitory effects with those of alpha-arbutin and arbutin on human tyrosinase. | 2003 Jul |
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Synthesis of hydroquinone-alpha-glucoside by alpha-glucosidase from baker's yeast. | 2005 Apr |
|
Modulating effects of a novel skin-lightening agent, alpha-lipoic acid derivative, on melanin production by the formation of DOPA conjugate products. | 2007 Mar 1 |
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Arbutin blocks defects in the ripple phase of DMPC bilayers by changing carbonyl organization. | 2007 May |
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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 May |
|
Opinion of the Scientific Committee on Consumer safety (SCCS)--Opinion on the safety of the use of α-arbutin in cosmetic products. | 2016 Feb |
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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admin
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Edited
Sat Dec 16 20:10:49 GMT 2023
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Sat Dec 16 20:10:49 GMT 2023
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Record UNII |
72VUP07IT5
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Record Status |
Validated (UNII)
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Record Version |
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SUB185343
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1363429
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