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
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 |
Doses
Dose | Population | Adverse events |
---|---|---|
2 % 1 times / day multiple, topical Studied dose Dose: 2 %, 1 times / day Route: topical Route: multiple Dose: 2 %, 1 times / day Sources: |
healthy, ADULT n = 59 Health Status: healthy Condition: skin Age Group: ADULT Sex: F Food Status: UNKNOWN Population Size: 59 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Effect of deoxyarbutin on melanogenesis: in vivo comparison with other melanogenesis inhibitor. | 2004 Jan-Feb |
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DeoxyArbutin: a novel reversible tyrosinase inhibitor with effective in vivo skin lightening potency. | 2005 Aug |
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DeoxyArbutin and its derivatives inhibit tyrosinase activity and melanin synthesis without inducing reactive oxygen species or apoptosis. | 2012 Oct |
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).
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