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Details

Stereochemistry ACHIRAL
Molecular Formula C14H12O4
Molecular Weight 244.2432
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIOXYBENZONE

SMILES

COc1ccc(c(c1)O)C(=O)c2ccccc2O

InChI

InChIKey=MEZZCSHVIGVWFI-UHFFFAOYSA-N
InChI=1S/C14H12O4/c1-18-9-6-7-11(13(16)8-9)14(17)10-4-2-3-5-12(10)15/h2-8,15-16H,1H3

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/5569329 and http://www.sun-protection-and-products-guide.com/sunscreen-ingredients.html

Dioxybenzone (benzophenone-8) is an organic compound used in sunscreen to block UVB and short-wave UVA rays. It is a derivative of benzophenone. It is insoluble in water, which lends to the ‘waterproof’ claims that sunscreens make. It’s approved for use in the US at a concentration of 3%.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Dioxybenzone

Approved Use

Dioxybenzone (benzophenone-8) is an organic compound used in sunscreen to block UVB and UVA rays.

Launch Date

9.2715837E11
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.
2001 Mar
[Estrogenic activity of ultraviolet absorbers and the related compounds].
2005 Aug
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Toxicokinetics and metabolisms of benzophenone-type UV filters in rats.
2008 Jun 27
Rat α-Fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities.
2012 Nov 19
Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and α-fetoprotein.
2015 Feb
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: Maximum FDA-approved concentration of Dioxybenzone in sunscreen 3%
The dose used in FDA sunscreen testing is 2 mg/cm2 of exposed skin. Sunscreen should be applied one-half hour before going outside, giving the skin time to absorb it. It should be reapplied at least every two hours outdoors, and immediately after swimming or heavy sweating. At least one ounce (two tablespoons) is needed to cover the entire body surface.
Route of Administration: Topical
In Vitro Use Guide
To clarify the photoreactivity of Dioxybenzone, the ROS assay was undertaken with the use of Dioxybenzone at 200 uM
Name Type Language
DIOXYBENZONE
INN   MART.   MI   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
BENZOPHENONE-8
INCI  
INCI  
Official Name English
DIOXYBENZONE [MART.]
Common Name English
DIOXYBENZONE [USP-RS]
Common Name English
METHANONE, (2-HYDROXY-4-METHOXYPHENYL)(2-HYDROXYPHENYL)-
Systematic Name English
2,2'-DIHYDROXY-4-METHOXYBENZOPHENONE
Systematic Name English
SPECTRA-SORB UV 24
Brand Name English
DIOXYBENZONE [USP MONOGRAPH]
Common Name English
DIOXYBENZONE [MI]
Common Name English
DIOXYBENZONE [WHO-DD]
Common Name English
NSC-56769
Code English
DIOXYBENZONE [VANDF]
Common Name English
DIOXYBENZONE [INN]
Common Name English
DIOXYBENZONE [USAN]
Common Name English
BENZOPHENONE-8 [INCI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C851
Created by admin on Fri Jun 25 20:55:40 UTC 2021 , Edited by admin on Fri Jun 25 20:55:40 UTC 2021
CFR 21 CFR 352.10
Created by admin on Fri Jun 25 20:55:40 UTC 2021 , Edited by admin on Fri Jun 25 20:55:40 UTC 2021
CFR 21 CFR 352.20
Created by admin on Fri Jun 25 20:55:40 UTC 2021 , Edited by admin on Fri Jun 25 20:55:40 UTC 2021
Code System Code Type Description
FDA UNII
B762XZ551X
Created by admin on Fri Jun 25 20:55:40 UTC 2021 , Edited by admin on Fri Jun 25 20:55:40 UTC 2021
PRIMARY
DRUG BANK
DB11221
Created by admin on Fri Jun 25 20:55:40 UTC 2021 , Edited by admin on Fri Jun 25 20:55:40 UTC 2021
PRIMARY
NCI_THESAURUS
C74399
Created by admin on Fri Jun 25 20:55:40 UTC 2021 , Edited by admin on Fri Jun 25 20:55:40 UTC 2021
PRIMARY
CAS
131-53-3
Created by admin on Fri Jun 25 20:55:40 UTC 2021 , Edited by admin on Fri Jun 25 20:55:40 UTC 2021
PRIMARY
RXCUI
23350
Created by admin on Fri Jun 25 20:55:40 UTC 2021 , Edited by admin on Fri Jun 25 20:55:40 UTC 2021
PRIMARY RxNorm
EVMPD
SUB07206MIG
Created by admin on Fri Jun 25 20:55:40 UTC 2021 , Edited by admin on Fri Jun 25 20:55:40 UTC 2021
PRIMARY
MERCK INDEX
M4602
Created by admin on Fri Jun 25 20:55:40 UTC 2021 , Edited by admin on Fri Jun 25 20:55:40 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
205-026-8
Created by admin on Fri Jun 25 20:55:40 UTC 2021 , Edited by admin on Fri Jun 25 20:55:40 UTC 2021
PRIMARY
DRUG CENTRAL
3159
Created by admin on Fri Jun 25 20:55:40 UTC 2021 , Edited by admin on Fri Jun 25 20:55:40 UTC 2021
PRIMARY
ChEMBL
CHEMBL1326877
Created by admin on Fri Jun 25 20:55:40 UTC 2021 , Edited by admin on Fri Jun 25 20:55:40 UTC 2021
PRIMARY
PUBCHEM
8569
Created by admin on Fri Jun 25 20:55:40 UTC 2021 , Edited by admin on Fri Jun 25 20:55:40 UTC 2021
PRIMARY
MESH
C004839
Created by admin on Fri Jun 25 20:55:40 UTC 2021 , Edited by admin on Fri Jun 25 20:55:40 UTC 2021
PRIMARY
WIKIPEDIA
DIOXYBENZONE
Created by admin on Fri Jun 25 20:55:40 UTC 2021 , Edited by admin on Fri Jun 25 20:55:40 UTC 2021
PRIMARY
EPA CompTox
131-53-3
Created by admin on Fri Jun 25 20:55:40 UTC 2021 , Edited by admin on Fri Jun 25 20:55:40 UTC 2021
PRIMARY
INN
2097
Created by admin on Fri Jun 25 20:55:40 UTC 2021 , Edited by admin on Fri Jun 25 20:55:40 UTC 2021
PRIMARY
USP_CATALOG
1214004
Created by admin on Fri Jun 25 20:55:40 UTC 2021 , Edited by admin on Fri Jun 25 20:55:40 UTC 2021
PRIMARY USP-RS