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 |
|
| 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 |
|
| Arbutin blocks defects in the ripple phase of DMPC bilayers by changing carbonyl organization. | 2007 May |
|
| 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
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 20:10:49 UTC 2023
by
admin
on
Sat Dec 16 20:10:49 UTC 2023
|
| Record UNII |
72VUP07IT5
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
SUB185343
Created by
admin on Sat Dec 16 20:10:49 UTC 2023 , Edited by admin on Sat Dec 16 20:10:49 UTC 2023
|
PRIMARY | |||
|
84380-01-8
Created by
admin on Sat Dec 16 20:10:49 UTC 2023 , Edited by admin on Sat Dec 16 20:10:49 UTC 2023
|
PRIMARY | |||
|
72VUP07IT5
Created by
admin on Sat Dec 16 20:10:50 UTC 2023 , Edited by admin on Sat Dec 16 20:10:50 UTC 2023
|
PRIMARY | |||
|
72VUP07IT5
Created by
admin on Sat Dec 16 20:10:50 UTC 2023 , Edited by admin on Sat Dec 16 20:10:50 UTC 2023
|
PRIMARY | |||
|
DB14109
Created by
admin on Sat Dec 16 20:10:50 UTC 2023 , Edited by admin on Sat Dec 16 20:10:50 UTC 2023
|
PRIMARY | |||
|
100000171735
Created by
admin on Sat Dec 16 20:10:50 UTC 2023 , Edited by admin on Sat Dec 16 20:10:50 UTC 2023
|
PRIMARY | |||
|
158637
Created by
admin on Sat Dec 16 20:10:50 UTC 2023 , Edited by admin on Sat Dec 16 20:10:50 UTC 2023
|
PRIMARY | |||
|
DTXSID20233358
Created by
admin on Sat Dec 16 20:10:50 UTC 2023 , Edited by admin on Sat Dec 16 20:10:50 UTC 2023
|
PRIMARY | |||
|
1363429
Created by
admin on Sat Dec 16 20:10:50 UTC 2023 , Edited by admin on Sat Dec 16 20:10:50 UTC 2023
|
PRIMARY | RxNorm |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
