ContaminantDB: Diazolidinyl urea

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-11-23 23:08:08 UTC

Update Date

2016-10-28 10:02:16 UTC

Accession Number

CHEM002599

Identification

Common Name

Diazolidinyl urea

Class

Small Molecule

Description

Diazolidinyl urea is an antimicrobial preservative that acts as a formaldehyde releaser. It is used in many cosmetics, skin care products, shampoos and conditioners, as well as a wide range of products including bubble baths, baby wipes and household detergents. Diazolidinyl urea is found in the commercially available preservative Germaben. Diazolidinyl urea may cause contact dermatitis. Its toxicity is also due to it's ability to release formaldehyde, which is believed to be carcinogenic. (3)

Contaminant Sources

Cosmetic Chemicals
HPV EPA Chemicals
IARC Carcinogens Group 1
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Cosmetic Toxin
Household Toxin
Organic Compound
Synthetic Compound

Chemical Structure

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

Synonyms

Value	Source
Germall II	MeSH
5-(1,3-Bis(hydroxymethyl)ureido)-1,3-bis(hydroxymethyl)imidazol-2,5(3H,5H)dione	MeSH
Diazolidinylurea	MeSH

Chemical Formula

C₈H₁₄N₄O₇

Average Molecular Mass

278.219 g/mol

Monoisotopic Mass

278.086 g/mol

CAS Registry Number

78491-02-8

IUPAC Name

1-[1,3-bis(hydroxymethyl)-2,5-dioxoimidazolidin-4-yl]-1,3-bis(hydroxymethyl)urea

Traditional Name

diazolidinyl urea

SMILES

OCNC(=O)N(CO)C1N(CO)C(=O)N(CO)C1=O

InChI Identifier

InChI=1S/C8H14N4O7/c13-1-9-7(18)10(2-14)5-6(17)12(4-16)8(19)11(5)3-15/h5,13-16H,1-4H2,(H,9,18)

InChI Key

SOROIESOUPGGFO-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as allantoins. These are heterocyclic compounds containing an imiazolidine ring substituted by a ketone group at positions 2 and 5, and an urea at position 4.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Imidazolidines

Direct Parent

Allantoins

Alternative Parents

Substituents

Allantoin
Alpha-amino acid or derivatives
Ureide
N-acyl urea
Dicarboximide
Urea
Carbonic acid derivative
Alkanolamine
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

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

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	1000 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	29.1 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-3.8	ChemAxon
logS	-0.98	ALOGPS
pKa (Strongest Acidic)	12.69	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.88 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	56.02 m³·mol⁻¹	ChemAxon
Polarizability	24.28 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0390000000-145fdee36d825d8eb8f0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xr-0970000000-c286f9a082ee211e393e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0930000000-fe1c7215f52092ff48e7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-016s-0190000000-2ae8acf690107ac94f31	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-2090000000-c8ec0d76384135b50089	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006w-4920000000-3b81c399001b1e89090b	Spectrum

Toxicity Profile

Route of Exposure

Oral (2) ; inhalation (2) ; dermal (2)

Mechanism of Toxicity

Diazolidinyl urea is a formaldehyde releaser. It is likely that formaldehyde toxicity occurs when intracellular levels saturate formaldehyde dehydrogenase activity, allowing the unmetabolized intact molecule to exert its effects. Formaldehyde is known to form cross links between protein and DNA and undergo metabolic incorporation into macromolecules (DNA, RNA, and proteins). (2, 3)

Metabolism

Formaldehyde may be absorbed following inhalation, oral, or dermal exposure. It is an essential metabolic intermediate in all cells and is produced during the normal metabolism of serine, glycine, methionine, and choline and also by the demethylation of N-, S-, and O-methyl compounds. Exogenous formaldehyde is metabolized to formate by the enzyme formaldehyde dehydrogenase at the initial site of contact. After oxidation of formaldehyde to formate, the carbon atom is further oxidized to carbon dioxide or incorporated into purines, thymidine, and amino acids via tetrahydrofolatedependent one-carbon biosynthetic pathways. Formaldehyde is not stored in the body and is excreted in the urine (primarily as formic acid), incorporated into other cellular molecules, or exhaled as carbon dioxide. (2)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

1, carcinogenic to humans (for formaldehyde). (1)

Uses/Sources

Diazolidinyl urea is an antimicrobial preservative used in many cosmetics, skin care products, shampoos and conditioners, as well as a wide range of products including bubble baths, baby wipes and household detergents. Diazolidinyl urea is found in the commercially available preservative Germaben. (3)

Minimum Risk Level

Not Available

Health Effects

Diazolidinyl urea releases formaldehyde, a known human carcinogen. (2, 3)

Symptoms

Some people have a contact allergy to diazolidinyl urea, causing dermatitis. (3)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

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

Diazolidinyl urea

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

62277

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

Diazolidinyl urea (CHEM002599)

Structure for CHEM002599: Diazolidinyl urea