BENZOPHENONE-5

First approved in 1964

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H11O6S.Na
Molecular Weight	330.288
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].COC1=CC(O)=C(C=C1S([O-])(=O)=O)C(=O)C2=CC=CC=C2

InChI

InChIKey=KJCLYACXIWMFCC-UHFFFAOYSA-M

InChI=1S/C14H12O6S.Na/c1-20-12-8-11(15)10(7-13(12)21(17,18)19)14(16)9-5-3-2-4-6-9;/h2-8,15H,1H3,(H,17,18,19);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	C14H11O6S
Molecular Weight	307.299
Charge	-1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.fda.gov/drugs/guidancecomplianceregulatoryinformation/guidances/ucm330694.htm
Curator's Comment: Description was created using several sources including: https://www.ncbi.nlm.nih.gov/pubmed/?term=11407932; https://www.ncbi.nlm.nih.gov/pubmed/1729569; https://books.google.com/books?id=AmqJDAAAQBAJ&pg=PA209&lpg=PA209&dq=SULISOBENZONE+was+first+developed+by&source=bl&ots=RZpF_2Yj4K&sig=Cjei8l5DytTpZyrMSIYfMF3grtE&hl=en&sa=X&ved=0ahUKEwiKrPjK_KHPAhWFWT4KHXG4A6UQ6AEIOTAF#v=onepage&q=SULISOBENZONE%20was%20first%20developed%20by&f=false

Sulisobenzone (benzophenone-4) is an ingredient for use in sunscreens which protects the skin from damage by UVB and short-wave UVA ultraviolet light. The Food and Drug Administration (FDA) has approved the use of Benzophenone-4 as safe and effective, over-the-counter (OTC) sunscreen ingredient. Sulisobenzone is a subject to the FDA 2011 sunscreen final rule: it can be marketed without approved drug applications (without NDAs or ANDAs), must bear the statement of identity “sunscreen" and contain the information about SPF test. However it is said to be widely used in cosmetic products not labeled as sunscreens such as creams, moisturizers, shampoos and other hair care products, nail polish, lipsticks and lip balms. Sulisobenzone may cause contact dermatitis when used in cosmetics and toiletries. Benzophenone 4 is tested as 10%. It was reported that 10% sulisobenzone enhance skin penetration of the moderately lipophilic herbicide 2,4-D.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Sunburn 84 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=67796e08-17c0-4401-bee3-9e64249da380&type=display	Preventing		Approved 8429	BENEFIT TRIPLE PERFORMING FACIAL BROAD SPECTRUM SPF15 Approved Use Helps prevent sunburn. Decreases the risk of skin cancer and early skin aging caused by the sun.

C_max

Value	Dose	Co-administered	Analyte	Population
1.8 μg/g EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32088184/	0.1 mg single, topical dose: 0.1 mg route of administration: Topical experiment type: SINGLE co-administered:		SULISOBENZONE unknown	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
23.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32088184/	0.1 mg single, topical dose: 0.1 mg route of administration: Topical experiment type: SINGLE co-administered:		SULISOBENZONE unknown	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32088184/	0.1 mg single, topical dose: 0.1 mg route of administration: Topical experiment type: SINGLE co-administered:		SULISOBENZONE unknown	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-003719	http://www.3bsc.com/index/pro_info.php?id=25610
AA Blocks	AA00I7WH	http://www.aablocks.com/goods/Goods/detail?id=AA00I7WH
AHH Chemical co.,ltd	MT-34652	http://www.ahhchemical.com/product/MT-34652.html
AK Scientific, Inc. (AKSCI)	70691	http://www.aksci.com/item_detail.php?cat=70691
Aaron Chemicals	AR00I8O9	http://www.aaronchem.com/4065-45-6
AbMole Bioscience	M5983	http://www.abmole.com/products/sulisobenzone.html
Acadechem	ACDS-035859	http://www.acadechemical.com/product/110558
Accela ChemBio Inc	SY036839	http://www.accelachem.com/cn/search.html?keyword=SY036839&attname=GoodsCode
Achemo Scientific Limited	AC-14565	http://www.achemo.com/search/?Keyword= 4065-45-6
Achemtek	0104-008574	http://www.achemtek.com/4065-45-6
Adooq BioScience	A16154	https://www.adooq.com/sulisobenzone.html
Alfa Aesar	L12912	https://www.alfa.com/en/catalog/L12912/
Alfa Chemistry	AP4065456-A	https://reagents.alfa-chemistry.com/product/sulisobenzone-cas-4065-45-6-11163.html
Alfa Chemistry	AP4065456-B	https://reagents.alfa-chemistry.com/product/sulisobenzone-cas-4065-45-6-11164.html
Alfa Chemistry	4065-45-6	https://www.alfa-chemistry.com/2-hydroxy-4-methoxybenzophenone-5-sulfonic-acid-cas-4065-45-6-item-291884.htm
Alinda	ALBB-025816	http://alinda.ru/finechem_en_.html?i=ALBB-025816
Allbio Pharm Co., Ltd	AD05386	http://www.allbiopharm.com/product/n/AD05386
Angene	AGN-PC-0JKF0E	http://www.angenechemical.com/productshow/AGN-PC-0JKF0E.html
Ark Pharm	AK110733	http://www.arkpharminc.com/products/4065-45-6.html
Aurum Pharmatech LLC	K-8670	http://www.Aurumpharmatech.com/Product/ProductDetails/K_8670
Avantor Inc	TCH0466-025G	https://us.vwr.com/store/product/10049643/2-hydroxy-4-methoxy-5-sulfobenzophenone-hydrate-98-0-by-titrimetric-analysis-contains-5-10-isopropyl-alcohol
Avantor Inc	TCH0466-500G	https://us.vwr.com/store/product/10049643/2-hydroxy-4-methoxy-5-sulfobenzophenone-hydrate-98-0-by-titrimetric-analysis-contains-5-10-isopropyl-alcohol
Avantor Inc	700004-112	https://us.vwr.com/store/product/21572571/2-hydroxy-4-methoxy-5-sulfobenzophenone-97-0
Avantor Inc	700004-116	https://us.vwr.com/store/product/21572571/2-hydroxy-4-methoxy-5-sulfobenzophenone-97-0
Avantor Inc	700004-118	https://us.vwr.com/store/product/21572571/2-hydroxy-4-methoxy-5-sulfobenzophenone-97-0
BLD Pharm	BD17071	http://www.bldpharm.com/products/4065-45-6.html
BioSynth	J-509633	https://www.biosynth.com/en/products/all-products/products/J-509633.html
Chem Scene	CS-4610	http://www.chemscene.com/4065-45-6.html
ChemMol	30107548	http://www.chemmol.com/chemmol/30107548.html
ChemMol	49414705	http://www.chemmol.com/chemmol/49414705.html
Chemspace	CSSB00016990401	https://chem-space.com/CSSB00016990401
China MainChem Co., Ltd	4065-45-6	https://www.mainchem.com/product/china-2-hydroxy-4-methoxybenzophenone-5-sulfonic-acid-supplier/
Clearsynth	CS-EB-02040	https://www.clearsynth.com/en/CSEB02040.html
Clearsynth	CS-ER-02032	https://www.clearsynth.com/en/CSER02032.html
DC Chemicals	DC10246	http://www.dcchemicals.com/product_show-Sulisobenzone.html
Debye Scientific	DB-049626	http://www.debyesci.com/cas_4065-45-6.html
Finetech	FT-0612547	http://www.finetechnology-ind.com/prod/detail/pub/4065-45-6.html
Glentham Life Sciences	GK2691	http://www.glentham.com/products/product/GK2691/
LGC Standards	DRE-C10545000	https://www.lgcstandards.com/US/en/p/DRE-C10545000
Lab Network	LN00193400	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00193400
Matrix Scientific	98199	https://www.matrixscientific.com/098199.html
MedChem Express	HY-B1162	https://www.medchemexpress.com/Sulisobenzone.html
MuseChem	I003483	https://www.musechem.com/product/I003483.html
Oakwood	238749	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=119748&ExtHyperLink=1
Renno Tech	RL03566	http://www.rennotech.com/product_show.asp?id=3886
Selleck Chemicals	S4652	http://www.selleckchem.com/products/sulisobenzone.html
Sigma-Aldrich	S454664_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/s454664
Sigma-Aldrich	09649_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/09649?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	50194_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/50194?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1642100_USP	https://www.sigmaaldrich.com/catalog/product/usp/1642100?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S020202	http://www.sinfoobiotech.com/product/1023600
Smolecule	S599493	https://www.smolecule.com/products/s599493
TCI (Tokyo Chemical Industry)	H0466	http://www.tcichemicals.com/eshop/en/us/commodity/H0466/index.html
THE BioTek	bt-305358	https://www.thebiotek.com/product/others/bt-305358
VladaChem	VL274519-10G	https://www.vladachem.com/product.php?products=4065-45-6
Yuhao Chemical	LT1751	http://www.chemyuhao.com/4065-45-6.html
abcr GmbH	AB174103	http://www.abcr.com/shop/en/AB174103
eNovation Chemicals	D653618	https://www.enovationchem.com/ProductDetails.asp?ProductID=D653618
eNovation Chemicals	D914082	https://www.enovationchem.com/ProductDetails.asp?ProductID=D914082
iChemical	EBD55074	http://www.ichemical.com/chemicals/cas-4065-45-6
mcule	MCULE-1313711100	https://mcule.com/MCULE-1313711100/

PubMed

Title	Date	PubMed
Determination of UV-filters in sunscreens by HPLC.	2001 Apr	11371063
[Photoaggravated contact allergy and contact photoallergy caused by ketoprofen: 19 cases].	2001 Oct	11907961
Reactive oxygen species assay-based risk assessment of drug-induced phototoxicity: classification criteria and application to drug candidates.	2008 Aug 5	18455898
Solid-phase extraction followed by liquid chromatography-tandem mass spectrometry for the determination of hydroxylated benzophenone UV absorbers in environmental water samples.	2009 Nov 10	19854348
Development of a fully automated sequential injection solid-phase extraction procedure coupled to liquid chromatography to determine free 2-hydroxy-4-methoxybenzophenone and 2-hydroxy-4-methoxybenzophenone-5-sulphonic acid in human urine.	2010 Apr 7	20363401
The UV-absorber benzophenone-4 alters transcripts of genes involved in hormonal pathways in zebrafish (Danio rerio) eleuthero-embryos and adult males.	2011 Jan 15	20937294

Patents

Sample Use Guides

In Vivo Use Guide

Apply sunscreen that contains Avobenzone 3.00% Octinoxate 7.49% Octocrylene 2.00% Sulisobenzone 1.50% liberally 15 minutes before sun exposure. Reapply at least every 2 hours. Children under 6 months of age: ask a doctor.

Route of Administration: Topical

In Vitro Use Guide

After 1 hr incubation with five test concentrations of each chemical compound, epidermis was then exposed or not to UVA at a non-cytotoxic dose (50 J/sq cm). 18 hr after UVA exposure, cellular damage was evaluated measuring cytotoxicity by MTT conversion test.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:00:10 GMT 2023` Edited by `admin` on `Fri Dec 15 16:00:10 GMT 2023`
Record UNII	853Z42ZYAS
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BENZOPHENONE-5

Official Name

English

SODIUM 5-BENZOYL-4-HYDROXY-2-METHOXYBENZENESULFONATE

Systematic Name

English

BENZENESULFONIC ACID, 5-BENZOYL-4-HYDROXY-2-METHOXY-, SODIUM SALT

Common Name

English

SULISOBENZONE SODIUM

Common Name

English

BENZENESULFONIC ACID, 5-BENZOYL-4-HYDROXY-2-METHOXY-, SODIUM SALT (1:1)

Common Name

English

BENZOPHENONE 5

Common Name

English

ASL 24ST

Code

English

SODIUM 2-HYDROXY-4-METHOXYBENZOPHENONE-5-SULPHONATE

Common Name

English

UVISTAT 1121

Brand Name

English

SODIUM BENZOPHENONE-2-HYDROXY-4-METHOXY-5-SULFONATE

Common Name

English

2-HYDROXY-4-METHOXYBENZOPHENONE-5-SULFONIC ACID SODIUM SALT

Common Name

English

SULIBENZONE

Common Name

English

SODIUM BENZOPHENONE-2-HYDROXY-4-METHOXY-5-SULPHONATE

Common Name

English

BENZENESULFONIC ACID, 5-BENZOYL-4-HYDROXY-2-METHOXY-, MONOSODIUM SALT

Common Name

English

BENZOPHENONE-5 [INCI]

Common Name

English

SODIUM 2-HYDROXY-4-METHOXYBENZOPHENONE-5-SULFONATE

Common Name

English

UVIN 1MS40

Brand Name

English

SODIUM 5-BENZOYL-4-HYDROXY-2-METHOXYBENZENESULPHONATE

Systematic Name

English

Code System Code Type Description

DRUG BANK

DBSALT002279