U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 TETRAHYDROPYRANYLOXY PHENOL

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
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
n = 59
Health Status: healthy
Condition: skin
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 59
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Effect of deoxyarbutin on melanogenesis: in vivo comparison with other melanogenesis inhibitor.
2004 Jan-Feb
DeoxyArbutin: a novel reversible tyrosinase inhibitor with effective in vivo skin lightening potency.
2005 Aug
DeoxyArbutin and its derivatives inhibit tyrosinase activity and melanin synthesis without inducing reactive oxygen species or apoptosis.
2012 Oct
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).
Name Type Language
TETRAHYDROPYRANYLOXY PHENOL
INCI  
INCI  
Official Name English
TETRAHYDROPYRANYLOXY PHENOL, (±)-
Common Name English
PHENOL, 4-((TETRAHYDRO-2H-PYRAN-2-YL)OXY)-
Systematic Name English
DEOXYARBUTIN
Common Name English
TETRAHYDROPYRANYLOXY PHENOL [INCI]
Common 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 Sat Dec 16 01:20:16 GMT 2023 , Edited by admin on Sat Dec 16 01:20:16 GMT 2023
PRIMARY
PUBCHEM
11745519
Created by admin on Sat Dec 16 01:20:16 GMT 2023 , Edited by admin on Sat Dec 16 01:20:16 GMT 2023
PRIMARY
FDA UNII
RG969BY5EN
Created by admin on Sat Dec 16 01:20:16 GMT 2023 , Edited by admin on Sat Dec 16 01:20:16 GMT 2023
PRIMARY
CAS
53936-56-4
Created by admin on Sat Dec 16 01:20:16 GMT 2023 , Edited by admin on Sat Dec 16 01:20:16 GMT 2023
PRIMARY