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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
Structure of DEOXYARBUTIN

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

HIDE SMILES / InChI

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.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse 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
Health Status: healthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
DeoxyArbutin and its derivatives inhibit tyrosinase activity and melanin synthesis without inducing reactive oxygen species or apoptosis.
2012-10
Study on the stability of deoxyArbutin in an anhydrous emulsion system.
2011
Determination of the thermodegradation of deoxyArbutin in aqueous solution by high performance liquid chromatography.
2010-10-15
Effects of hydroquinone and its glucoside derivatives on melanogenesis and antioxidation: Biosafety as skin whitening agents.
2009-09
Mechanism of tyrosinase inhibition by deoxyArbutin and its second-generation derivatives.
2008-12
Comparative efficacy and safety of deoxyarbutin, a new tyrosinase-inhibiting agent.
2006-03-22
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
Patents

Sample Use Guides

3% moistening cream on a 100 cm2. 12 weeks daily treatment
Route of Administration: Topical
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
by admin
on Mon Mar 31 20:48:13 GMT 2025
Edited
by admin
on Mon Mar 31 20:48:13 GMT 2025
Record UNII
RG969BY5EN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEOXYARBUTIN
Common Name English
TETRAHYDROPYRANYLOXY PHENOL
INCI  
INCI  
Preferred Name English
TETRAHYDROPYRANYLOXY PHENOL, (±)-
Common Name English
PHENOL, 4-((TETRAHYDRO-2H-PYRAN-2-YL)OXY)-
Systematic Name English
GIRLITE DA 100
Brand Name English
(±)-TETRAHYDROPYRANYLOXY PHENOL
Systematic Name English
4-(TETRAHYDRO-2H-PYRAN-2-YLOXY)PHENOL
Systematic Name English
4-HYDROXYPHENYL TETRAHYDROPYRANYL ETHER
Systematic Name English
4-((2-TETRAHYDROPYRANYL)OXY)PHENOL
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID10968728
Created by admin on Mon Mar 31 20:48:13 GMT 2025 , Edited by admin on Mon Mar 31 20:48:13 GMT 2025
PRIMARY
PUBCHEM
11745519
Created by admin on Mon Mar 31 20:48:13 GMT 2025 , Edited by admin on Mon Mar 31 20:48:13 GMT 2025
PRIMARY
FDA UNII
RG969BY5EN
Created by admin on Mon Mar 31 20:48:13 GMT 2025 , Edited by admin on Mon Mar 31 20:48:13 GMT 2025
PRIMARY
CAS
53936-56-4
Created by admin on Mon Mar 31 20:48:13 GMT 2025 , Edited by admin on Mon Mar 31 20:48:13 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Potent inhibitor
COMPETITIVE INHIBITOR
IC50
Related Record Type Details
ACTIVE MOIETY
Active tyrosinase inhibitor that can promote apoptosis of melanoma cells, and has skin whitening and anti-tumor activity[1][2][3]