Compounds > diallyl phthalate
Page last updated: 2024-12-05

diallyl phthalate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Diallyl phthalate (DAP) is a synthetic plasticizer used primarily in polyvinyl chloride (PVC) resins. It is produced through a reaction between phthalic anhydride and allyl alcohol. DAP has been studied due to its potential endocrine disrupting properties, particularly its ability to disrupt androgen signaling, which could lead to reproductive and developmental problems. Additionally, DAP has been associated with increased risk of cancer in animal studies. Its use is regulated in many countries due to these health concerns.'

Cross-References

ID SourceID
PubMed CID8560
CHEMBL ID1329372
SCHEMBL ID15174
MeSH IDM0140842

Synonyms (71)

Synonym
dapon 35
nsc-7667
nsc7667
nci-c50657
wln: 1u2ovr bvo2u1
allyl phthalate
phthalic acid, diallyl ester
diallyl phthalate
dapon r
o-phthalic acid, diallyl ester
131-17-9
hsdb 4169
nsc 7667
di-2-propenyl 1,2-benzenedicarboxylate
diallylester phthalic acid
diallylphthalate
brn 1880877
ai3-02574
einecs 205-016-3
ccris 1361
diallylester kyseliny ftalove [czech]
inchi=1/c14h14o4/c1-3-9-17-13(15)11-7-5-6-8-12(11)14(16)18-10-4-2/h3-8h,1-2,9-10h
1,2-benzenedicarboxylic acid, di-2-propenyl ester
NCGC00091365-01
diallyl phthalate, 97%
NCGC00091365-02
bis(prop-2-enyl) benzene-1,2-dicarboxylate
smr001253767
MLS002415725
P0290
phthalic acid diallyl ester
NCGC00091365-03
NCGC00091365-04
diallylester kyseliny ftalove
unii-f79l0ul6st
f79l0ul6st ,
4-09-00-03188 (beilstein handbook reference)
1,2-benzenedicarboxylic acid, 1,2-di-2-propen-1-yl ester
ec 205-016-3
dtxcid70392
dtxsid7020392 ,
tox21_300135
NCGC00259510-01
NCGC00254197-01
cas-131-17-9
tox21_201961
HMS2267F17
25053-15-0
FT-0624597
AKOS015891274
SCHEMBL15174
diallyl phthalate [hsdb]
CHEMBL1329372
143318-73-4
diallyl ester of phthalic acid
diallyl ester o-phthalic acid
rx 3-1-530 (salt/mix)
nonflammable decobest da (salt/mix)
dap monomer
rx 1-501n (salt/mix)
1,2-benzenedicarboxylicaciddi-2-propenylester
mfcd00008646
phthalic acid, bis-allyl ester
diallyl phthalate, analytical standard
J-005948
di-allyl phthalate
BS-14891
Q2161731
diprop-2-enyl benzene-1,2-dicarboxylate
1,2-bis(prop-2-en-1-yl) benzene-1,2-dicarboxylate
F87052

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"The objective of this study was to evaluate the developmental toxic potential of diallyl phthalate (DAP) in rats."( Evaluation of the developmental toxicity of diallyl phthalate administered orally to rats.
Gallissot, F; Sabaté, JP; Saillenfait, AM, 2008)		0.83

Dosage Studied

ExcerptRelevanceReference
" Monoallyl phthalate (MAP), allyl alcohol, 3-hydroxypropylmercapturic acid (HPMA), and an unidentified polar metabolite (PM) were found in the urine of rats and mice dosed with DAP."( Examination of the differential hepatotoxicity of diallyl phthalate in rats and mice.
Carter, DE; Eigenberg, DA; Schram, KH; Sipes, IG, 1986)		0.52
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (27)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency3.54810.003245.467312,589.2998AID2517
interleukin 8Homo sapiens (human)Potency74.97800.047349.480674.9780AID651758
AR proteinHomo sapiens (human)Potency29.67160.000221.22318,912.5098AID1259243; AID1259247
retinoid X nuclear receptor alphaHomo sapiens (human)Potency33.69590.000817.505159.3239AID1159527; AID1159531
farnesoid X nuclear receptorHomo sapiens (human)Potency54.94100.375827.485161.6524AID743217
estrogen nuclear receptor alphaHomo sapiens (human)Potency54.10180.000229.305416,493.5996AID743075
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_aHomo sapiens (human)Potency67.54470.001723.839378.1014AID743083
chromobox protein homolog 1Homo sapiens (human)Potency50.11870.006026.168889.1251AID540317
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency71.30530.000627.21521,122.0200AID651741; AID743202
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency5.01190.031610.279239.8107AID884; AID885
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Rap guanine nucleotide exchange factor 4Homo sapiens (human)Potency28.18383.981146.7448112.2020AID720708
GABA theta subunitRattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency5.01191.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (10)

Processvia Protein(s)Taxonomy
adaptive immune responseRap guanine nucleotide exchange factor 4Homo sapiens (human)
G protein-coupled receptor signaling pathwayRap guanine nucleotide exchange factor 4Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayRap guanine nucleotide exchange factor 4Homo sapiens (human)
calcium-ion regulated exocytosisRap guanine nucleotide exchange factor 4Homo sapiens (human)
regulation of exocytosisRap guanine nucleotide exchange factor 4Homo sapiens (human)
insulin secretionRap guanine nucleotide exchange factor 4Homo sapiens (human)
positive regulation of insulin secretionRap guanine nucleotide exchange factor 4Homo sapiens (human)
regulation of synaptic vesicle cycleRap guanine nucleotide exchange factor 4Homo sapiens (human)
Ras protein signal transductionRap guanine nucleotide exchange factor 4Homo sapiens (human)
regulation of insulin secretionRap guanine nucleotide exchange factor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
guanyl-nucleotide exchange factor activityRap guanine nucleotide exchange factor 4Homo sapiens (human)
protein bindingRap guanine nucleotide exchange factor 4Homo sapiens (human)
cAMP bindingRap guanine nucleotide exchange factor 4Homo sapiens (human)
protein-macromolecule adaptor activityRap guanine nucleotide exchange factor 4Homo sapiens (human)
small GTPase bindingRap guanine nucleotide exchange factor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
cytosolRap guanine nucleotide exchange factor 4Homo sapiens (human)
plasma membraneRap guanine nucleotide exchange factor 4Homo sapiens (human)
membraneRap guanine nucleotide exchange factor 4Homo sapiens (human)
hippocampal mossy fiber to CA3 synapseRap guanine nucleotide exchange factor 4Homo sapiens (human)
plasma membraneRap guanine nucleotide exchange factor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1745845Primary qHTS for Inhibitors of ATXN expression
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (26)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (7.69)18.7374
1990's0 (0.00)18.2507
2000's11 (42.31)29.6817
2010's9 (34.62)24.3611
2020's4 (15.38)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 42.46

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index42.46 (24.57)
Research Supply Index3.30 (2.92)
Research Growth Index4.19 (4.65)
Search Engine Demand Index61.16 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (42.46)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other26 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
acetone
methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).		2.0310ketone body;
methyl ketone;
propanones;
volatile organic compound		EC 3.5.1.4 (amidase) inhibitor;
human metabolite;
polar aprotic solvent
phthalic acid
phthalic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7178. phthalic acid : A benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions.		3.2760benzenedicarboxylic acidhuman xenobiotic metabolite
1-propanol
1-Propanol: A colorless liquid made by oxidation of aliphatic hydrocarbons that is used as a solvent and chemical intermediate.. propan-1-ol : The parent member of the class of propan-1-ols that is propane in which a hydrogen of one of the methyl groups is replaced by a hydroxy group.		1.9610propan-1-ols;
short-chain primary fatty alcohol		metabolite;
protic solvent
butylbenzyl phthalate
spatozoate: structure in first source		2.7930benzyl ester
dibutyl phthalate
Dibutyl Phthalate: A plasticizer used in most plastics and found in water, air, soil, plants and animals. It may have some adverse effects with long-term exposure.. dibutyl phthalate : A phthalate ester that is the diester obtained by the formal condensation of the carboxy groups of phthalic acid with two molecules of butan-1-ol. Although used extensively as a plasticiser, it is a ubiquitous environmental contaminant that poses a risk to humans.		3.3660diester;
phthalate ester		EC 3.2.1.20 (alpha-glucosidase) inhibitor;
environmental contaminant;
metabolite;
plasticiser;
teratogenic agent
bisphenol a
4,4'-isopropylidene diphenol: stimulates proliferative responses and cytokine productions of murine spleen cells and thymus cells in vitro. bisphenol : By usage, the methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone). The term also includes analogues in the the methylene (or substituted methylene) group has been replaced by a heteroatom.. bisphenol A : A bisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups.		2.9540bisphenolendocrine disruptor;
environmental contaminant;
xenobiotic;
xenoestrogen
dicyclohexyl phthalate
[no description available]		2.0310diester;
phthalate ester
diethyl phthalate
diethyl phthalate: structure. diethyl phthalate : The diethyl ester of benzene-1,2-dicarboxylic acid.		8.3660diester;
ethyl ester;
phthalate ester		neurotoxin;
plasticiser;
teratogenic agent
diisobutyl phthalate
diisobutyl phthalate : A phthalate ester that is the diester obtained by the formal condensation of the carboxy groups of phthalic acid with two molecules of isobutanol.		2.9330diester;
phthalate ester		plasticiser;
PPAR modulator;
teratogenic agent
phenyl ether
diphenyl ether : An aromatic ether in which the oxygen is attached to two phenyl substituents. It has been found in muscat grapes and vanilla.		2.0310aromatic etherplant metabolite
allyl alcohol
allyl alcohol: structure. allylic alcohol : An alcohol where the hydroxy group is attached to a saturated carbon atom adjacent to a double bond (R groups may be H, organyl, etc.).. allyl alcohol : A propenol in which the C=C bond connects C-2 and C-3. It is has been found in garlic (Allium sativum). Formerly used as a herbicide for the control of various grass and weed seeds.		1.9610primary allylic alcohol;
propenol		antibacterial agent;
fungicide;
herbicide;
insecticide;
plant metabolite
chlorobenzene
[no description available]		2.0310monochlorobenzenessolvent
diethylhexyl phthalate
Diethylhexyl Phthalate: An ester of phthalic acid. It appears as a light-colored, odorless liquid and is used as a plasticizer for many resins and elastomers.. bis(2-ethylhexyl) phthalate : A phthalate ester that is the bis(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.		2.7630diester;
phthalate ester		androstane receptor agonist;
apoptosis inhibitor;
plasticiser
dimethyl phthalate
dimethyl phthalate: used as plasticizer in computer mouse; structure		3.1850diester;
methyl ester;
phthalate ester
malondialdehyde
Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.		2.1310dialdehydebiomarker
monomethyl phthalate
monomethyl phthalate: structure in first source		2.2110methyl ester;
phthalic acid monoester
amcinonide
[no description available]		2.0110diester;
phthalate ester
monoethyl phthalate
monoethyl phthalate: structure in first source. monoethyl phthalate : A phthalic acid monoester resulting from the condensation of one of the carboxy groups of phthalic acid with ethanol.		2.2110ethyl ester;
phthalic acid monoester		metabolite
hydroxyurea
diethyl diallylmalonate: structure in first source		2.0510fatty acid ester
2,2',4,4'-tetrabromodiphenyl ether
[no description available]		2.7230aromatic ether;
organobromine compound
ConditionIndicatedRelationship StrengthStudiesTrials
Innate Inflammatory Response
[description not available]		02.0510
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.0510
Chromosome-Defective Micronuclei
[description not available]		02.0310
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.0310
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		02.0410
Fetal Death
Death of the developing young in utero. BIRTH of a dead FETUS is STILLBIRTH.		02.0410
Abnormalities, Drug-Induced
Congenital abnormalities caused by medicinal substances or drugs of abuse given to or taken by the mother, or to which she is inadvertently exposed during the manufacture of such substances. The concept excludes abnormalities resulting from exposure to non-medicinal chemicals in the environment.		02.0410
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		02.0410