Page last updated: 2024-12-06

tris(1,3-dichloro-2-propyl)phosphate

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

Cross-References

ID SourceID
PubMed CID26177
CHEMBL ID3182032
CHEBI ID143729
SCHEMBL ID333198
MeSH IDM0067025

Synonyms (70)

Synonym
tris[2-chloro-1-(chloromethyl)ethyl] phosphate
13674-87-8
tris-(1,3-dichloro-2-propyl)phosphate
tris(1,3-dichloroisopropyl)phosphate
fyrol fr 2
inchi=1/c9h15cl6o4p/c10-1-7(2-11)17-20(16,18-8(3-12)4-13)19-9(5-14)6-15/h7-9h,1-6h
crp (fireproofing agent)
tris(1-chloromethyl-2-chloroethyl)phosphate
tris(2-chloro-1-(chloromethyl)ethyl) phosphate
tri(beta,beta'-dichloroisopropyl)phosphate
pf 38/3
einecs 237-159-2
fyrol fr-2
ccris 6284
tdcpp
tris(1,3-dichloro-2-propyl)phosphate
emulsion 212
1,3-dichloro-2-propanol phosphate (3:1)
fosforan troj-(1,3-dwuchloroizopropylowy) [polish]
pf 38
brn 1715458
hsdb 4364
tris(2-chloro-1-(chloromethyl)ethyl)phosphate
CRP ,
2-propanol, 1,3-dichloro-, phosphate (3:1)
tris(1,3-dichloro-2-propyl) phosphate
phosphoric acid tris(1,3-dichloro-2-propyl) ester
FT-0654115
P0269
tris(1,3-dichloropropan-2-yl) phosphate
CHEBI:143729
A807122
tris(1,3-dichloro-2-propyl) phosphate;tris(1,3-dichloro-2-propyl)phosphate
NCGC00247923-01
NCGC00247923-02
3-01-00-01473 (beilstein handbook reference)
b1prv4g0t0 ,
unii-b1prv4g0t0
fosforan troj-(1,3-dwuchloroizopropylowy)
ec 237-159-2
2-propanol, 1,3-dichloro-, 2,2',2''-phosphate
tox21_300194
NCGC00254047-01
NCGC00259715-01
dtxsid9026261 ,
tox21_202166
cas-13674-87-8
dtxcid206261
tdcipp
S12389
AKOS015856734
tris(1,3-dichloro-2-propyl)phosphate [hsdb]
tdcpp [mi]
SCHEMBL333198
phosphoric acid tris(1,3-dichloro-2-propyl)ester
tri(.beta.,.beta.'-dichloroisopropyl)phosphate
tris[2-chloro-1-(chloromethyl)ethyl] phosphate #
ASLWPAWFJZFCKF-UHFFFAOYSA-N
HY-108712
CS-8011
CHEMBL3182032
tris(1,3-dichloro-2-propyl) phosphate, 95%
mfcd00083121
tdcpp, analytical standard
J-006902
tris(1.3-dichloro-2-propyl) phosphate
phosphoric acid tris-(2-chloro-1-chloromethyl-ethyl) ester
Q2454085
tris-(1,3-dichloroisopropyl) phosphate standard 50 microg/ml in acetonitrile
fyrol fr 2,tcpp

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" TDCPP was toxic to hepatocytes (LC₅₀ = 60."( Effects of tris(1,3-dichloro-2-propyl) phosphate and tris(1-chloropropyl) phosphate on cytotoxicity and mRNA expression in primary cultures of avian hepatocytes and neuronal cells.
Chiu, S; Crump, D; Kennedy, SW, 2012
)
0.38
"Tris(1,3-dichloro-2-propyl) phosphate (TDCIPP) has been frequently detected in environmental media and has adverse health effect on wildlife and humans."( Acute Exposure to Tris(1,3-dichloro-2-propyl) Phosphate (TDCIPP) Causes Hepatic Inflammation and Leads to Hepatotoxicity in Zebrafish.
Agrawal, I; Giesy, JP; Gong, Z; Letcher, RJ; Li, G; Li, J; Liu, C; Su, G; Wang, J; Yu, L, 2016
)
0.43
" Due to the hazardous effects of many of these chemicals, manufacturers are developing next generation potential less toxic alternatives."( Acute mixture toxicity of halogenated chemicals and their next generation counterparts on zebrafish embryos.
Abdel-Moneim, A; Godfrey, A; Sepúlveda, MS, 2017
)
0.46
" Developmental toxicity is a major concern of OPFRs' adverse health effects."( Exposure to tris(1,3-dichloro-2-propyl) phosphate (TDCPP) induces vascular toxicity through Nrf2-VEGF pathway in zebrafish and human umbilical vein endothelial cells.
Kang, J; Qiu, J; Shi, X; Wei, Y; Xing, X; Zhong, X, 2019
)
0.51
"As the application and environmental release of tris(1,3-dichloro-2-propyl) phosphate (TDCIPP) are being increased rapidly, serious concerns have been raised regarding its adverse effects on human health."( Sub-chronic exposure to Tris(1,3-dichloro-2-propyl) phosphate induces sex-dependent hepatotoxicity in rats.
Hu, X; Li, X; Wang, S, 2019
)
0.51
" The ubiquitous distribution and persistence of TDCPP in aquatic environment have led to concerns over its possible toxic effects on aquatic organism."( Toxic effect and mechanism of tris (1,3-dichloro-2-propyl)phosphate (TDCPP) on the marine alga Phaeodactylum tricornutum.
Jian, X; Liu, Q; Ma, W; Tang, X; Wang, Y; Yang, Y; Zhang, X, 2020
)
0.56
"Humans are exposed to many xenobiotics simultaneously, but little is known about the toxic effects based on chemical-chemical interactions."( Impact of Mixture Effects between Emerging Organic Contaminants on Cytotoxicity: A Systems Biological Understanding of Synergism between Tris(1,3-dichloro-2-propyl)phosphate and Triphenyl Phosphate.
Chen, D; Cheng, HS; Fang, M; Jia, S; Koh, D; Liu, M; Peng, B; Tan, NS; Wang, Y; Warth, B; Zhang, Y, 2020
)
0.76
" The DEPs associated with toxic effects of TDCIPP were then screened by use of Gene Ontology and the Kyoto Encyclopedia of Genes and Genomes for enrichment analysis."( Proteomic analysis using isobaric tags for relative and absolute quantification technology reveals mechanisms of toxic effects of tris (1,3-dichloro-2-propyl) phosphate on RAW264.7 macrophage cells.
Giesy, JP; Wang, P; Wang, R; Wei, S; Zhang, S; Zhang, W, 2022
)
0.72

Bioavailability

ExcerptReferenceRelevance
" Microplastics (plastic particles < 5 mm) and nanoplastics (plastic particles < 100 nm) can interact with organic pollutants already present in the aquatic environment, potentially acting as carriers for pollutants entering organisms and thus influencing the bioavailability and toxicity of those pollutants."( Parental transfer of nanopolystyrene-enhanced tris(1,3-dichloro-2-propyl) phosphate induces transgenerational thyroid disruption in zebrafish.
Duan, X; Liu, Z; Ren, X; Zhao, X, 2021
)
0.62

Dosage Studied

ExcerptRelevanceReference
" Dermal uptake and percutaneous penetration of the OPEs were studied in a Franz diffusion cell system using human skin dosed with a mixture of OPEs in an ethanol:toluene (4:1) solution."( Dermal uptake and percutaneous penetration of organophosphate esters in a human skin ex vivo model.
Clausen, PA; Frederiksen, M; Jensen, NM; Knudsen, LE; Nielsen, F; Nielsen, JB; Stapleton, HM; Sørensen, JA; Sørensen, LS; Vorkamp, K; Webster, TF, 2018
)
0.48
" Exposure to TDCPP resulted in a dose-response decrease of micoalgal biomass."( Metabolomics reveals that tris(1,3-dichloro-2-propyl)phosphate (TDCPP) causes disruption of membrane lipids in microalga Scenedesmus obliquus.
Huang, X; Laserna, AKC; Li, SFY; Wang, L, 2020
)
0.86
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
trialkyl phosphate
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (22)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
RAR-related orphan receptor gammaMus musculus (house mouse)Potency27.42530.006038.004119,952.5996AID1159521; AID1159523
GLI family zinc finger 3Homo sapiens (human)Potency1.44220.000714.592883.7951AID1259369; AID1259392
AR proteinHomo sapiens (human)Potency41.47750.000221.22318,912.5098AID1259243; AID1259247; AID743035; AID743036; AID743042; AID743054; AID743063
estrogen receptor 2 (ER beta)Homo sapiens (human)Potency61.36180.000657.913322,387.1992AID1259378
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency40.68510.001022.650876.6163AID1224838; AID1224839; AID1224893
progesterone receptorHomo sapiens (human)Potency7.26000.000417.946075.1148AID1346795
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency13.61810.000214.376460.0339AID720691; AID720692; AID720719
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency40.83400.003041.611522,387.1992AID1159552; AID1159555
retinoid X nuclear receptor alphaHomo sapiens (human)Potency16.42010.000817.505159.3239AID1159527; AID1159531
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency50.93940.001530.607315,848.9004AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403
farnesoid X nuclear receptorHomo sapiens (human)Potency49.00070.375827.485161.6524AID743217; AID743220
pregnane X nuclear receptorHomo sapiens (human)Potency20.15730.005428.02631,258.9301AID1346982
estrogen nuclear receptor alphaHomo sapiens (human)Potency44.16180.000229.305416,493.5996AID1259244; AID1259248; AID743069; AID743075; AID743078; AID743079
peroxisome proliferator activated receptor gammaHomo sapiens (human)Potency43.64120.001019.414170.9645AID743191
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_aHomo sapiens (human)Potency61.39770.001723.839378.1014AID743083
v-jun sarcoma virus 17 oncogene homolog (avian)Homo sapiens (human)Potency7.11440.057821.109761.2679AID1159526; AID1159528
Histone H2A.xCricetulus griseus (Chinese hamster)Potency11.24540.039147.5451146.8240AID1224845
thyroid hormone receptor beta isoform 2Rattus norvegicus (Norway rat)Potency64.68580.000323.4451159.6830AID743065; AID743067
Voltage-dependent calcium channel gamma-2 subunitMus musculus (house mouse)Potency61.36180.001557.789015,848.9004AID1259244
Glutamate receptor 2Rattus norvegicus (Norway rat)Potency61.36180.001551.739315,848.9004AID1259244
ATPase family AAA domain-containing protein 5Homo sapiens (human)Potency68.24100.011917.942071.5630AID651632
Ataxin-2Homo sapiens (human)Potency68.24100.011912.222168.7989AID651632
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (18)

Processvia Protein(s)Taxonomy
cell population proliferationATPase family AAA domain-containing protein 5Homo sapiens (human)
positive regulation of B cell proliferationATPase family AAA domain-containing protein 5Homo sapiens (human)
nuclear DNA replicationATPase family AAA domain-containing protein 5Homo sapiens (human)
signal transduction in response to DNA damageATPase family AAA domain-containing protein 5Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediatorATPase family AAA domain-containing protein 5Homo sapiens (human)
isotype switchingATPase family AAA domain-containing protein 5Homo sapiens (human)
positive regulation of DNA replicationATPase family AAA domain-containing protein 5Homo sapiens (human)
positive regulation of isotype switching to IgG isotypesATPase family AAA domain-containing protein 5Homo sapiens (human)
DNA clamp unloadingATPase family AAA domain-containing protein 5Homo sapiens (human)
regulation of mitotic cell cycle phase transitionATPase family AAA domain-containing protein 5Homo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediatorATPase family AAA domain-containing protein 5Homo sapiens (human)
positive regulation of cell cycle G2/M phase transitionATPase family AAA domain-containing protein 5Homo sapiens (human)
negative regulation of receptor internalizationAtaxin-2Homo sapiens (human)
regulation of translationAtaxin-2Homo sapiens (human)
RNA metabolic processAtaxin-2Homo sapiens (human)
P-body assemblyAtaxin-2Homo sapiens (human)
stress granule assemblyAtaxin-2Homo sapiens (human)
RNA transportAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
protein bindingATPase family AAA domain-containing protein 5Homo sapiens (human)
ATP bindingATPase family AAA domain-containing protein 5Homo sapiens (human)
ATP hydrolysis activityATPase family AAA domain-containing protein 5Homo sapiens (human)
DNA clamp unloader activityATPase family AAA domain-containing protein 5Homo sapiens (human)
DNA bindingATPase family AAA domain-containing protein 5Homo sapiens (human)
RNA bindingAtaxin-2Homo sapiens (human)
epidermal growth factor receptor bindingAtaxin-2Homo sapiens (human)
protein bindingAtaxin-2Homo sapiens (human)
mRNA bindingAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
plasma membraneGlutamate receptor 2Rattus norvegicus (Norway rat)
Elg1 RFC-like complexATPase family AAA domain-containing protein 5Homo sapiens (human)
nucleusATPase family AAA domain-containing protein 5Homo sapiens (human)
cytoplasmAtaxin-2Homo sapiens (human)
Golgi apparatusAtaxin-2Homo sapiens (human)
trans-Golgi networkAtaxin-2Homo sapiens (human)
cytosolAtaxin-2Homo sapiens (human)
cytoplasmic stress granuleAtaxin-2Homo sapiens (human)
membraneAtaxin-2Homo sapiens (human)
perinuclear region of cytoplasmAtaxin-2Homo sapiens (human)
ribonucleoprotein complexAtaxin-2Homo sapiens (human)
cytoplasmic stress granuleAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Research

Studies (87)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (10.34)18.7374
1990's0 (0.00)18.2507
2000's3 (3.45)29.6817
2010's59 (67.82)24.3611
2020's16 (18.39)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 30.62

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index30.62 (24.57)
Research Supply Index4.50 (2.92)
Research Growth Index5.85 (4.65)
Search Engine Demand Index38.54 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (30.62)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (2.25%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other87 (97.75%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]