T3DB: Glutaral

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

Targets (3)

Record Information

Version

2.0

Creation Date

2014-09-11 05:18:55 UTC

Update Date

2014-12-24 20:26:58 UTC

Accession Number

T3D4844

Identification

Common Name

Glutaral

Class

Small Molecule

Description

Glutaral is used as an antimicrobial agent in sugar mills and as a fixing agent in the immobilisation of glucose isomerase enzyme preparations for use in the manufacture of high fructose corn syrup A polymerized isomer of glutaraldehyde known as polycycloglutaracetal is a fertilizer for aquatic plants. It is claimed that it provides a bioavailable source of carbon for higher plants that is not available to algae. Though not marketed as such due to federal regulations, the biocidal effect of glutaraldehyde kills most algae at concentrations of 0.5 - 5.0 ppm. These levels are not harmful to most aquatic fauna and flora. Adverse reactions have been observed by some aquarists at these concentrations in some aquatic mosses, liverworts, and vascular plants. Glutaraldehyde is a colorless liquid with a pungent odor used to disinfect medical and dental equipment. It is also used for industrial water treatment and as a chemical preservative. Glutaraldehyde is an oily liquid at room temperature (density 1.06 g/mL), and miscible with water, alcohol, and benzene. It is used as a tissue fixative in electron microscopy. It is employed as an embalming fluid, is a component of leather tanning solutions, and occurs as an intermediate in the production of certain industrial chemicals. Glutaraldehyde is frequently used in biochemistry applications as an amine-reactive homobifunctional crosslinker. The oligomeric state of proteins can be examined through this application. However, it is toxic, causing severe eye, nose, throat and lung irritation, along with headaches, drowsiness and dizziness. It is a main source of occupational asthma among health care providers. Glutaral has been shown to exhibit antibiotic function (1). Glutaral belongs to the family of Aldehydes. These are organic compounds containing the aldehyde functional group.

Compound Type

Aldehyde
Fertilizer
Food Toxin
Household Toxin
Industrial/Workplace Toxin
Lachrymator
Metabolite
Organic Compound
Preservative
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
1,3-Diformyl propane
1,3-Diformylpropane
1,5-Pentanedial
1,5-Pentanedione
Aldehyd glutarowy
Aldesan
Aldesen
Alhydex
Aqucar
Bactron K31
Cidex
Cidex 7
Coldcide-25 microbiocide
Dioxopentane
Diswart
Gludesin
Glutaclean
Glutaral(usan)
Glutaral, INN, USAN
Glutaraldehyd
Glutaraldehyde
GLUTARALDEHYDE, 25% SOLN
Glutaralum
Glutardialdehyde
Glutarex 28
Glutaric acid dialdehyde
Glutaric aldehyde
Glutaric dialdehyde
Glutarol
Glutarol-1,5-pentanedial
Gluteraldehyde
Glutural
Hospex
Novaruca
Pentane-1,5-dial
Pentanedial, homopolymer
Poly(glutaraldehyde)
Polyglutaraldehyde
Potentiated acid glutaraldehyde
Protectol GDA, GT 50
PTD
Relugan GT
Relugan GT 50
Relugan GTW
Sonacide
Sporicidin
Sterihyde
Sterihyde L
Ucarcide
Ucarcide 225
Ucarcide 250
Ucarset
Veruca-sep
Verucasep
Virsal

Chemical Formula

C₅H₈O₂

Average Molecular Mass

100.116 g/mol

Monoisotopic Mass

100.052 g/mol

CAS Registry Number

111-30-8

IUPAC Name

pentanedial

Traditional Name

glutaraldehyde

SMILES

O=CCCCC=O

InChI Identifier

InChI=1S/C5H8O2/c6-4-2-1-3-5-7/h4-5H,1-3H2

InChI Key

InChIKey=SXRSQZLOMIGNAQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-hydrogen aldehydes

Alternative Parents

Substituents

Alpha-hydrogen aldehyde
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dialdehyde (CHEBI:64276 )
a small molecule (CPD-9052 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

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

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	-14°C
Boiling Point	Not Available
Solubility	Not Available
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	64 g/L	ALOGPS
logP	0.93	ALOGPS
logP	-0.27	ChemAxon
logS	-0.19	ALOGPS
pKa (Strongest Acidic)	16.71	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	26.29 m³·mol⁻¹	ChemAxon
Polarizability	10.33 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-0a4ee2dd933655592450	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01ri-9700000000-f57095cd51cc37e0d7a3	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9500000000-dd92f21c1ce5119db510	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9300000000-76b0fc068fee42644fc2	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000j-9800000000-94fe793f87572c27bb9a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-0a4ee2dd933655592450	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01ri-9700000000-f57095cd51cc37e0d7a3	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9500000000-dd92f21c1ce5119db510	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9300000000-76b0fc068fee42644fc2	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000j-9800000000-94fe793f87572c27bb9a	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ki6-9100000000-cfa97d859341d5a8a98c	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-3900000000-bc108f2306fdca4e0382	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-9600000000-60975f1f307715d9b0d3	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-3412a4cfb16ff54d74e4	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-81901fd58364994a5875	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9000000000-7ff4a53524c469d839d9	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-5385f2190cb9325cbf48	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052b-9000000000-01268815ce26388873d1	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00e9-9000000000-bb0306a62f1938089426	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-888cc9796657744c62a9	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-5a379556e2dd729948e1	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9000000000-106ecb37822a8cbb59a8	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aor-9000000000-382f529883be84d59740	2021-09-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-c4b5ba9226999878f5b6	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View 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)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

64276

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

PTD

ACToR ID

Not Available

Wikipedia Link

Pentanedial

References

Synthesis Reference

Not Available

MSDS

T3D4844.pdf

General References

Hayama T: [Pharmacological approach to control American foulbrood of honeybees]. Nihon Yakurigaku Zasshi. 1997 Oct;110(4):183-93. [9396023 ]
Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Transient receptor potential cation channel subfamily A member 1

General Function:: Temperature-gated cation channel activity
Specific Function:: Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:: TRPA1
Uniprot ID:: O75762
Molecular Weight:: 127499.88 Da

References

Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]

Target Details

2. Nuclear receptor subfamily 1 group I member 2

General Function:: Zinc ion binding
Specific Function:: Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
Gene Name:: NR1I2
Uniprot ID:: O75469
Molecular Weight:: 49761.245 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	1.05 uM	NVS_NR_hPXR	Novascreen

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Target Details

3. Androgen receptor

General Function:: Zinc ion binding
Specific Function:: Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:: AR
Uniprot ID:: P10275
Molecular Weight:: 98987.9 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	4.02 uM	NVS_NR_hAR	Novascreen

References

Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

Glutaral (T3D4844)

Structure for T3D4844: Glutaral

Targets

References

Binding/Activity Constants

References

Binding/Activity Constants

References