ContaminantDB: Ensulizole

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 04:25:26 UTC

Update Date

2016-10-28 10:03:07 UTC

Accession Number

CHEM017519

Identification

Common Name

Ensulizole

Class

Small Molecule

Description

Ensulizole, also known as 2-phenylbenzimidazole-5-sulfonic acid, is a water-soluble sunscreen agent that absorbs strongly at UV-B wavelengths. It is commonly found in cosmetic products and sunscreen formulas in combination with other UV filter compounds due to its minimal protection against UV-A wavelengths. Due to its water solubility, ensulizole is commonly used in products formulated to feel light and less oily [A32259]. It was demonstrated by studies that ensulizole treatment provided protection against cyclobutane pyrimidine dimers and photosensitized the formation of oxidized guanine bases after UV-A or UV-B exposure [A27151]. According to the FDA, the maximal approved concentration of ensulizole is 148 mM although concentrations ranging between 74 and 148mM can be found in commercial sunscreen products [A27151].

Contaminant Sources

Cosmetic Chemicals
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Phenylbenzimidazole sulfonic acid	Kegg
Phenylbenzimidazole sulfonate	Generator
Phenylbenzimidazole sulphonate	Generator
Phenylbenzimidazole sulphonic acid	Generator
Eusolex 232	MeSH
2-Phenylbenzimidazole-5-sulfonic acid, monosodium salt	MeSH
2-Phenylbenzimidazole-5-sulfonic acid	MeSH
Novantisol	MeSH
2-Phenyl-3H-benzimidazole-5-sulfonate	Generator
2-Phenyl-3H-benzimidazole-5-sulphonate	Generator
2-Phenyl-3H-benzimidazole-5-sulphonic acid	Generator
Ensulizole	MeSH
2-Phenyl-1H-1,3-benzodiazole-6-sulfonate	Generator
2-Phenyl-1H-1,3-benzodiazole-6-sulphonate	Generator
2-Phenyl-1H-1,3-benzodiazole-6-sulphonic acid	Generator

Chemical Formula

C₁₃H₁₀N₂O₃S

Average Molecular Mass

274.290 g/mol

Monoisotopic Mass

274.041 g/mol

CAS Registry Number

27503-81-7

IUPAC Name

2-phenyl-1H-1,3-benzodiazole-6-sulfonic acid

Traditional Name

2-phenyl-3H-1,3-benzodiazole-5-sulfonic acid

SMILES

OS(=O)(=O)C1=CC2=C(C=C1)N=C(N2)C1=CC=CC=C1

InChI Identifier

InChI=1S/C13H10N2O3S/c16-19(17,18)10-6-7-11-12(8-10)15-13(14-11)9-4-2-1-3-5-9/h1-8H,(H,14,15)(H,16,17,18)

InChI Key

UVCJGUGAGLDPAA-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylbenzimidazoles. Phenylbenzimidazoles are compounds containing a phenylbenzimidazole skeleton, which consists of a benzimidazole moiety where its imidazole ring is attached to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzimidazoles

Sub Class

Phenylbenzimidazoles

Direct Parent

Phenylbenzimidazoles

Alternative Parents

Substituents

Phenylbenzimidazole
2-phenylimidazole
Arylsulfonic acid or derivatives
1-sulfo,2-unsubstituted aromatic compound
Monocyclic benzene moiety
Benzenoid
Azole
Imidazole
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Sulfonyl
Heteroaromatic compound
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Hydrocarbon derivative
Organosulfur compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.32 g/L	ALOGPS
logP	1.03	ALOGPS
logP	-0.14	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	-2.2	ChemAxon
pKa (Strongest Basic)	4.93	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.05 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.69 m³·mol⁻¹	ChemAxon
Polarizability	27.73 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-00di-0090000000-7987784c7869933fe7d2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-006x-0950000000-41e7f48b728ad64e2644	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0006-0900000000-15af96954e5768106935	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-00di-0090000000-7bfcf4b4c271c9c450c9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-00di-0190000000-bf171a8f939edc704a3f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0006-0900000000-ec980d27ce16d09dfb19	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0006-0900000000-315f70e7c22cbfa1a163	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00dl-0690000000-0e948fdb1c99ee63de22	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00dl-0790000000-50f2eb115b89406ee8c4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0090000000-293262bfb0afdd3c114a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0190000000-00d18a90bdaa92bd1855	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-0900000000-f2465c2ecb95ddaf72a5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-0390000000-5d983cc9b05c5366df7d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0006-0910000000-7671f7a47a45dc44b67f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0007-0930000000-6e6b736bceb36ed18921	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0007-0910000000-127cca6ef93f3abc9dd9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-004i-0190000000-b10c1e57fd2019bc18c7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-004i-0190000000-2ed12c0d409c45ff98a1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-04f423b6a5f77b82785c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004l-0890000000-f96a3beb9e453e2c052c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-2910000000-3712de3671601ae5acb5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-b0dd8ad1adc39baba544	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-2190000000-edf1bc3beafcf2818416	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9300000000-1d504a0d0971aa846378	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB11115

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Ensulizole

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

33919

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Ensulizole (CHEM017519)

Structure for CHEM017519: Ensulizole