Page last updated: 2024-12-09

1,1-Bis(4-hydroxyphenyl)ethane

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

## 1,1-Bis(4-hydroxyphenyl)ethane: A Versatile Building Block

1,1-Bis(4-hydroxyphenyl)ethane, also known as **bisphenol A (BPA)**, is a **synthetic organic compound** with the chemical formula C₁₅H₁₆O₂. Its structure consists of two phenol rings connected to a central ethane bridge.

BPA's importance stems from its **versatility** as a **monomer** in the production of various **polymers** used in numerous applications:

**1. Polycarbonate Plastics:** BPA is the primary monomer for producing polycarbonate, a strong, clear, and impact-resistant thermoplastic. Polycarbonate is used in numerous consumer products like:
* **Food and beverage containers**
* **CDs and DVDs**
* **Eyeglasses**
* **Medical devices**
* **Automotive parts**

**2. Epoxy Resins:** BPA is also used as a building block for epoxy resins, commonly used in:
* **Coatings and adhesives**
* **Construction materials**
* **Electronics**

**3. Other Applications:**
* **Polyurethane foams**
* **Printing inks**
* **Flame retardants**

**Importance in Research:**

**a) Endocrine Disruptor:**
* **BPA has been identified as an endocrine disruptor.** This means it can interfere with the body's hormonal system, potentially leading to various health concerns, including reproductive problems, metabolic disorders, and increased risk of certain cancers.
* Extensive research investigates the **mechanisms of BPA's endocrine disruption, its impact on human health, and potential alternatives to BPA.**

**b) Environmental Concerns:**
* **BPA's widespread use and potential environmental release raise concerns about its impact on ecosystems and wildlife.**
* Research explores **BPA's fate in the environment, its persistence, and its potential bioaccumulation in organisms.**

**c) Material Science:**
* **BPA's unique properties make it a valuable component in various materials.**
* Research focuses on developing **new, improved, and sustainable alternatives to BPA** to address its potential health and environmental risks.

**d) Medical Applications:**
* Some research investigates potential **therapeutic applications of BPA derivatives** for conditions like cancer and Alzheimer's disease.

**Overall, 1,1-Bis(4-hydroxyphenyl)ethane remains a subject of significant research due to its widespread use, potential health and environmental concerns, and ongoing efforts to find suitable alternatives.**

Cross-References

ID SourceID
PubMed CID608116
CHEMBL ID2392656
CHEBI ID34029
SCHEMBL ID26946

Synonyms (38)

Synonym
AKOS015838553
1,1-bis(4-hydroxyphenyl)ethane
bisphenol e
4,4'-ethylidenebisphenol, 99%
hcnhnblsnvsjtj-uhfffaoysa-
inchi=1/c14h14o2/c1-10(11-2-6-13(15)7-3-11)12-4-8-14(16)9-5-12/h2-10,15-16h,1h3
4,4'-ethylidenediphenol
E0432
2081-08-5
4,4'-ethylidenebisphenol
4-[1-(4-hydroxyphenyl)ethyl]phenol
NCGC00248698-01
dtxcid9027867
tox21_200555
NCGC00258109-01
dtxsid3047891 ,
cas-2081-08-5
CHEMBL2392656 ,
chebi:34029 ,
4,4'-ethane-1,1-diyldiphenol
STL371128
SCHEMBL26946
1,1-bis(4-hydroxyphenyl) ethane
4,4'-(ethane-1,1-diyl)diphenol
tox21_304007
NCGC00357018-01
phenol, 4,4'-ethylidenebis-
J-514031
bisphenol e, analytical standard
AS-59101
phenol, 4,4'-ethylidenedi- (6ci,7ci,8ci); 4,4'-ethylidenebis[phenol]; 1,1-bis(4-hydroxyphenyl)ethane; 4,4'-ethylidenediphenol; bisphenol ad; bisphenol e
H48 ,
Q15726108
D80927
EN300-248172
bdbm50544708
CS-0154101
bisphenol e 100 microg/ml in methanol

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Nevertheless, only few studies have reported on the toxic effect of bisphenol analogues on phytoplankton."( Toxic effects of bisphenol A and its analogues on cyanobacteria Anabaena variabilis and Microcystis aeruginosa.
Czarny, K; Krawczyk, B; Szczukocki, D, 2021
)
0.62
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
diarylmethaneAny compound containing two aryl groups connected by a single C atom.
[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)
LuciferasePhotinus pyralis (common eastern firefly)Potency59.72500.007215.758889.3584AID1224835
RAR-related orphan receptor gammaMus musculus (house mouse)Potency43.43840.006038.004119,952.5996AID1159521; AID1159523
GLI family zinc finger 3Homo sapiens (human)Potency21.65300.000714.592883.7951AID1259369; AID1259392
AR proteinHomo sapiens (human)Potency24.47130.000221.22318,912.5098AID1259243; AID1259247; AID743035; AID743063
estrogen receptor 2 (ER beta)Homo sapiens (human)Potency13.85540.000657.913322,387.1992AID1259377; AID1259378; AID1259394
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency40.06660.001022.650876.6163AID1224838; AID1224839; AID1224893
progesterone receptorHomo sapiens (human)Potency29.45860.000417.946075.1148AID1346784; AID1346795
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency24.95280.003041.611522,387.1992AID1159552; AID1159553; AID1159555
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency54.10100.001530.607315,848.9004AID1224841; AID1224848; AID1224849
pregnane X nuclear receptorHomo sapiens (human)Potency53.32150.005428.02631,258.9301AID1346982
estrogen nuclear receptor alphaHomo sapiens (human)Potency22.95620.000229.305416,493.5996AID1259383; AID743069; AID743075; AID743077; AID743078; AID743079
peroxisome proliferator-activated receptor deltaHomo sapiens (human)Potency40.91130.001024.504861.6448AID743215
peroxisome proliferator activated receptor gammaHomo sapiens (human)Potency36.46220.001019.414170.9645AID743191
aryl hydrocarbon receptorHomo sapiens (human)Potency25.59350.000723.06741,258.9301AID743085
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_aHomo sapiens (human)Potency18.11880.001723.839378.1014AID743083
thyroid stimulating hormone receptorHomo sapiens (human)Potency54.48270.001628.015177.1139AID1224895
nuclear factor of kappa light polypeptide gene enhancer in B-cells 1 (p105), isoform CRA_aHomo sapiens (human)Potency0.002919.739145.978464.9432AID1159509
Histone H2A.xCricetulus griseus (Chinese hamster)Potency56.63630.039147.5451146.8240AID1224845; AID1224896
thyroid hormone receptor beta isoform 2Rattus norvegicus (Norway rat)Potency28.71640.000323.4451159.6830AID743065
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency27.71670.000627.21521,122.0200AID743202; AID743219
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Estrogen receptorHomo sapiens (human)IC50 (µMol)6.16000.00000.723732.7000AID1666467
Estrogen receptor betaHomo sapiens (human)IC50 (µMol)2.40000.00010.529432.7000AID1666468
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Estrogen receptorHomo sapiens (human)EC50 (µMol)10.00000.00000.53054.4000AID1666470
Estrogen receptor betaHomo sapiens (human)EC50 (µMol)1.39500.00000.47954.8900AID1666471
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (44)

Processvia Protein(s)Taxonomy
positive regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
antral ovarian follicle growthEstrogen receptorHomo sapiens (human)
epithelial cell developmentEstrogen receptorHomo sapiens (human)
chromatin remodelingEstrogen receptorHomo sapiens (human)
regulation of DNA-templated transcriptionEstrogen receptorHomo sapiens (human)
signal transductionEstrogen receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayEstrogen receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationEstrogen receptorHomo sapiens (human)
androgen metabolic processEstrogen receptorHomo sapiens (human)
male gonad developmentEstrogen receptorHomo sapiens (human)
negative regulation of gene expressionEstrogen receptorHomo sapiens (human)
positive regulation of phospholipase C activityEstrogen receptorHomo sapiens (human)
intracellular steroid hormone receptor signaling pathwayEstrogen receptorHomo sapiens (human)
intracellular estrogen receptor signaling pathwayEstrogen receptorHomo sapiens (human)
response to estradiolEstrogen receptorHomo sapiens (human)
regulation of toll-like receptor signaling pathwayEstrogen receptorHomo sapiens (human)
negative regulation of smooth muscle cell apoptotic processEstrogen receptorHomo sapiens (human)
negative regulation of canonical NF-kappaB signal transductionEstrogen receptorHomo sapiens (human)
negative regulation of DNA-binding transcription factor activityEstrogen receptorHomo sapiens (human)
response to estrogenEstrogen receptorHomo sapiens (human)
positive regulation of DNA-templated transcriptionEstrogen receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
fibroblast proliferationEstrogen receptorHomo sapiens (human)
positive regulation of fibroblast proliferationEstrogen receptorHomo sapiens (human)
stem cell differentiationEstrogen receptorHomo sapiens (human)
regulation of inflammatory responseEstrogen receptorHomo sapiens (human)
positive regulation of DNA-binding transcription factor activityEstrogen receptorHomo sapiens (human)
RNA polymerase II preinitiation complex assemblyEstrogen receptorHomo sapiens (human)
uterus developmentEstrogen receptorHomo sapiens (human)
vagina developmentEstrogen receptorHomo sapiens (human)
prostate epithelial cord elongationEstrogen receptorHomo sapiens (human)
prostate epithelial cord arborization involved in prostate glandular acinus morphogenesisEstrogen receptorHomo sapiens (human)
regulation of branching involved in prostate gland morphogenesisEstrogen receptorHomo sapiens (human)
mammary gland branching involved in pregnancyEstrogen receptorHomo sapiens (human)
mammary gland alveolus developmentEstrogen receptorHomo sapiens (human)
epithelial cell proliferation involved in mammary gland duct elongationEstrogen receptorHomo sapiens (human)
protein localization to chromatinEstrogen receptorHomo sapiens (human)
cellular response to estradiol stimulusEstrogen receptorHomo sapiens (human)
negative regulation of miRNA transcriptionEstrogen receptorHomo sapiens (human)
regulation of epithelial cell apoptotic processEstrogen receptorHomo sapiens (human)
regulation of transcription by RNA polymerase IIEstrogen receptorHomo sapiens (human)
cellular response to estrogen stimulusEstrogen receptorHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIEstrogen receptor betaHomo sapiens (human)
regulation of DNA-templated transcriptionEstrogen receptor betaHomo sapiens (human)
signal transductionEstrogen receptor betaHomo sapiens (human)
cell-cell signalingEstrogen receptor betaHomo sapiens (human)
negative regulation of cell growthEstrogen receptor betaHomo sapiens (human)
intracellular estrogen receptor signaling pathwayEstrogen receptor betaHomo sapiens (human)
positive regulation of DNA-templated transcriptionEstrogen receptor betaHomo sapiens (human)
positive regulation of DNA-binding transcription factor activityEstrogen receptor betaHomo sapiens (human)
cellular response to estradiol stimulusEstrogen receptor betaHomo sapiens (human)
regulation of transcription by RNA polymerase IIEstrogen receptor betaHomo sapiens (human)
cellular response to estrogen stimulusEstrogen receptor betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (29)

Processvia Protein(s)Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA bindingEstrogen receptorHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificEstrogen receptorHomo sapiens (human)
TFIIB-class transcription factor bindingEstrogen receptorHomo sapiens (human)
transcription coregulator bindingEstrogen receptorHomo sapiens (human)
transcription corepressor bindingEstrogen receptorHomo sapiens (human)
transcription coactivator bindingEstrogen receptorHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificEstrogen receptorHomo sapiens (human)
chromatin bindingEstrogen receptorHomo sapiens (human)
DNA-binding transcription factor activityEstrogen receptorHomo sapiens (human)
nuclear receptor activityEstrogen receptorHomo sapiens (human)
steroid bindingEstrogen receptorHomo sapiens (human)
protein bindingEstrogen receptorHomo sapiens (human)
calmodulin bindingEstrogen receptorHomo sapiens (human)
beta-catenin bindingEstrogen receptorHomo sapiens (human)
zinc ion bindingEstrogen receptorHomo sapiens (human)
TBP-class protein bindingEstrogen receptorHomo sapiens (human)
enzyme bindingEstrogen receptorHomo sapiens (human)
protein kinase bindingEstrogen receptorHomo sapiens (human)
nitric-oxide synthase regulator activityEstrogen receptorHomo sapiens (human)
nuclear estrogen receptor activityEstrogen receptorHomo sapiens (human)
nuclear estrogen receptor bindingEstrogen receptorHomo sapiens (human)
estrogen response element bindingEstrogen receptorHomo sapiens (human)
identical protein bindingEstrogen receptorHomo sapiens (human)
ATPase bindingEstrogen receptorHomo sapiens (human)
14-3-3 protein bindingEstrogen receptorHomo sapiens (human)
sequence-specific double-stranded DNA bindingEstrogen receptorHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingEstrogen receptor betaHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificEstrogen receptor betaHomo sapiens (human)
DNA bindingEstrogen receptor betaHomo sapiens (human)
nuclear steroid receptor activityEstrogen receptor betaHomo sapiens (human)
nuclear receptor activityEstrogen receptor betaHomo sapiens (human)
steroid bindingEstrogen receptor betaHomo sapiens (human)
protein bindingEstrogen receptor betaHomo sapiens (human)
zinc ion bindingEstrogen receptor betaHomo sapiens (human)
enzyme bindingEstrogen receptor betaHomo sapiens (human)
nuclear estrogen receptor activityEstrogen receptor betaHomo sapiens (human)
estrogen response element bindingEstrogen receptor betaHomo sapiens (human)
receptor antagonist activityEstrogen receptor betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
nucleusEstrogen receptorHomo sapiens (human)
nucleoplasmEstrogen receptorHomo sapiens (human)
transcription regulator complexEstrogen receptorHomo sapiens (human)
cytoplasmEstrogen receptorHomo sapiens (human)
Golgi apparatusEstrogen receptorHomo sapiens (human)
cytosolEstrogen receptorHomo sapiens (human)
plasma membraneEstrogen receptorHomo sapiens (human)
membraneEstrogen receptorHomo sapiens (human)
chromatinEstrogen receptorHomo sapiens (human)
euchromatinEstrogen receptorHomo sapiens (human)
protein-containing complexEstrogen receptorHomo sapiens (human)
nucleusEstrogen receptorHomo sapiens (human)
nucleusEstrogen receptor betaHomo sapiens (human)
nucleoplasmEstrogen receptor betaHomo sapiens (human)
mitochondrionEstrogen receptor betaHomo sapiens (human)
intracellular membrane-bounded organelleEstrogen receptor betaHomo sapiens (human)
chromatinEstrogen receptor betaHomo sapiens (human)
nucleusEstrogen receptor betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID1666472Antagonist activity at ERbeta (unknown origin) expressed in human HeLa cells assessed as inhibition of E2-induced transcriptional activity measured after 24 hrs by luciferase reporter gene assay based Schild plot analysis
AID1666468Displacement of [3H]17-beta estradiol from GST-fused human recombinant ERbeta ligand binding domain expressed in Escherichia coli BL21alpha cells incubated for 1 hr by liquid scintillation counting method
AID1666470Agonist activity at ERalpha (unknown origin) expressed in human HeLa cells assessed as transcriptional activation measured after 24 hrs by luciferase reporter gene assay
AID1666471Agonist activity at ERbeta (unknown origin) expressed in human HeLa cells assessed as transcriptional activation measured after 24 hrs by luciferase reporter gene assay
AID752867Inhibition of rabbit skeletal muscle sarco/endoplasmic reticulum calcium ATPase assessed as inhibition of ATP hydrolysis by spectrophotometric analysis2013Bioorganic & medicinal chemistry, Jul-01, Volume: 21, Issue:13
Structural requirements for inhibitory effects of bisphenols on the activity of the sarco/endoplasmic reticulum calcium ATPase.
AID1666467Displacement of [3H]17-beta estradiol from GST-fused human recombinant ERalpha ligand binding domain expressed in Escherichia coli BL21alpha cells incubated for 1 hr by liquid scintillation counting method
AID1666469Selectivity index, ratio of IC50 for GST-fused human recombinant ERalpha ligand binding domain expressed in Escherichia coli BL21alpha cells to IC50 for GST-fused human recombinant ERbeta ligand binding domain expressed in Escherichia coli BL21alpha cells
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's4 (25.00)24.3611
2020's12 (75.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.19

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

MetricThis Compound (vs All)
Research Demand Index12.19 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index5.03 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.19)

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%
Other16 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]