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158348

Sigma-Aldrich

4-(Benzyloxy)phenol

98%

Synonym(s):

4-(Phenylmethoxy)phenol, Hydroquinone monobenzyl ether

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About This Item

Linear Formula:
C6H5CH2OC6H4OH
CAS Number:
103-16-2
Molecular Weight:
200.23
Beilstein:
1958305
EC Number:
203-083-3
MDL number:
MFCD00002333
UNSPSC Code:
12352100
PubChem Substance ID:
24849729
NACRES:
NA.22

Assay

98%

form

solid

mp

119-120 °C (lit.)

SMILES string

Oc1ccc(OCc2ccccc2)cc1

InChI

1S/C13H12O2/c14-12-6-8-13(9-7-12)15-10-11-4-2-1-3-5-11/h1-9,14H,10H2

InChI key

VYQNWZOUAUKGHI-UHFFFAOYSA-N

Gene Information

human ... TYR(7299)
rat ... Ar(24208)

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Application

4-(Benzyloxy)phenol was used in the synthesis of bis(4-benzyloxyphenoxy)phenyl phosphine oxide. It was also used in the preparation of series of hetaryl-azophenol dyes via heterocyclic amines in nitrosyl sulphuric acid.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317,H319

Hazard Classifications

Eye Irrit. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis, spectral properties, biological activity and application of new 4-(benzyloxy) phenol derived azo dyes for polyester fiber dyeing.
Yousefi H, et al.
Journal of Molecular Liquids, 180, 51-58 (2013)
Jasper G van den Boorn et al.
The Journal of investigative dermatology, 131(6), 1240-1251 (2011-02-18)
In this study, we report the previously unknown mechanism of inducing robust anti-melanoma immunity by the vitiligo-inducing compound monobenzone. We show monobenzone to increase melanocyte and melanoma cell immunogenicity by forming quinone-haptens to the tyrosinase protein and by inducing the
Contact hypersensitivity to monobenzyl ether of hydroquinone used to treat vitiligo.
C C Lyon et al.
Contact dermatitis, 39(3), 132-133 (1998-10-15)
Jasper G van den Boorn et al.
PloS one, 5(5), e10626-e10626 (2010-05-26)
Presently melanoma still lacks adequate treatment options for metastatic disease. While melanoma is exceptionally challenging to standard regimens, it is suited for treatment with immunotherapy based on its immunogenicity. Since treatment-related skin depigmentation is considered a favourable prognostic sign during
Behrooz Kasraee et al.
Experimental dermatology, 15(7), 509-514 (2006-06-10)
Monobenzylether of hydroquinone (MBEH) has long been utilized for the depigmentation therapy of patients with extensive vitiligo. In this approach, the normally pigmented areas surrounding vitiligo lesions are depigmented to achieve a uniform skin tone. One of the important disadvantages
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