Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C11H14O3 |
| Molecular Weight | 194.2271 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=C(OC2CCCCO2)C=C1
InChI
InChIKey=GFBCWCDNXDKFRH-UHFFFAOYSA-N
InChI=1S/C11H14O3/c12-9-4-6-10(7-5-9)14-11-3-1-2-8-13-11/h4-7,11-12H,1-3,8H2
| Molecular Formula | C11H14O3 |
| Molecular Weight | 194.2271 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
Tetrahydropyranyloxy Phenol (Deoxyarbutin) is a skin lightening agent synthesized through removal of hydroxyl groups from the glucose side-chain of beta-arbutin. Deoxyarbutin demonstrated effective inhibition of mushroom tyrosinase in vitro with a Ki that is 10-fold lower that hydroquinone (HQ) and 350-fold lower than arbutin. Topical application of Deoxyarbutin on human xenografts resulted in a gradual and visually apparent skin lightening effect during an eight-week period. In a clinical trial, Deoxyarbutin facilitated fading of pre-tanned skin to a statistically significant greater extent than either HQ or no treatment. However, the overall conclusion of the Scientific Committee on Consumer Safety is that the use of deoxyarbutin up to 3% in face creams is not safe. Deoxyarbutin could combat melanoma in vitro and in vivo by inhibiting the proliferation and metastasis of tumour via a p38-mediated mitochondria associated apoptotic pathway.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3318 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16026582 |
0.05 µM [Ki] | ||
Target ID: WP400 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28775302 |
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Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28775302 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| DeoxyArbutin and its derivatives inhibit tyrosinase activity and melanin synthesis without inducing reactive oxygen species or apoptosis. | 2012-10 |
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| Study on the stability of deoxyArbutin in an anhydrous emulsion system. | 2011 |
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| Determination of the thermodegradation of deoxyArbutin in aqueous solution by high performance liquid chromatography. | 2010-10-15 |
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| Effects of hydroquinone and its glucoside derivatives on melanogenesis and antioxidation: Biosafety as skin whitening agents. | 2009-09 |
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| Mechanism of tyrosinase inhibition by deoxyArbutin and its second-generation derivatives. | 2008-12 |
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| Comparative efficacy and safety of deoxyarbutin, a new tyrosinase-inhibiting agent. | 2006-03-22 |
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| DeoxyArbutin: a novel reversible tyrosinase inhibitor with effective in vivo skin lightening potency. | 2005-08 |
|
| Effect of deoxyarbutin on melanogenesis: in vivo comparison with other melanogenesis inhibitor. | 2004-04-07 |
Sample Use Guides
3% moistening cream on a 100 cm2. 12 weeks daily treatment
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28775302
Cell viability was separately evaluated in six normal cell lines (NIH/3T3, HS68, HK-2, L02, HLECs and HUVECs cells) and two cancer cells (B16F10, LL/2), which had been treated with varying concentrations from 10 uM to 200 uM of TETRAHYDROPYRANYLOXY PHENOL for 24h. Results showed that TETRAHYDROPYRANYLOXY PHENOL significantly inhibited the proliferation of tumour cells including B16F10 cells and LL/2 cells, especially B16F10 cells (EC50=39.56 uM).
| Substance Class |
Chemical
Created
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RG969BY5EN
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Validated (UNII)
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TARGET -> INHIBITOR |
Potent inhibitor
COMPETITIVE INHIBITOR
IC50
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ACTIVE MOIETY |
Active tyrosinase inhibitor that can promote apoptosis of melanoma cells, and has skin whitening and anti-tumor activity[1][2][3]
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