9,9-bis(4-hydroxyphenyl)fluorene, also known as 9,9-di(4-hydroxyphenyl)fluorene, is a key monomer used in the synthesis of various polymers. It is characterized by its rigid, planar structure and two hydroxyl groups, which contribute to its ability to form strong intermolecular hydrogen bonds. This property allows it to be incorporated into polymers that exhibit high glass transition temperatures, improved mechanical strength, and enhanced thermal stability. 9,9-bis(4-hydroxyphenyl)fluorene is also known for its fluorescence properties, making it a promising candidate for applications in optoelectronic devices such as organic light-emitting diodes (OLEDs). Furthermore, its rigid structure and hydroxyl groups allow it to self-assemble into supramolecular structures, which find potential applications in fields like nanotechnology and drug delivery. The compound is typically synthesized through a multi-step process involving the reaction of fluorene with 4-hydroxybenzaldehyde in the presence of a strong base. The synthesis and properties of 9,9-bis(4-hydroxyphenyl)fluorene are actively studied to understand its potential in various fields, including polymer chemistry, materials science, and nanotechnology.'
fluorene-9-bisphenol: derivative of bisphenol A
ID Source | ID |
---|---|
PubMed CID | 76716 |
CHEMBL ID | 434829 |
CHEBI ID | 136855 |
SCHEMBL ID | 45826 |
Synonym |
---|
AC-4552 |
phenol, 4,4'-(9h-fluoren-9-ylidene)bis- |
ec 406-950-6 |
4,4'-(9-fluorenylidene)diphenol, 97% |
NCGC00164160-01 |
4,4'-(9h-fluorene-9,9-diyl)diphenol |
3236-71-3 |
4-[9-(4-hydroxyphenyl)-9h-fluoren-9-yl]phenol |
9,9-bis(p-hydroxyphenyl)fluorene |
bhpf |
4,4'-(9h-fluoren-9-ylidene)bisphenol |
fluorene-9-bisphenol |
bisphenol fluorenone |
CHEBI:136855 |
4,4'-(9-fluorenylidene)diphenol |
B1715 |
CHEMBL434829 |
9,9-bis(4-hydroxyphenyl)fluorene , |
4-[9-(4-hydroxyphenyl)fluoren-9-yl]phenol |
AKOS005255127 |
NCGC00255689-01 |
tox21_301584 |
dtxsid5037731 , |
cas-3236-71-3 |
dtxcid3017731 |
A821249 |
4,4-(9-fluorenylidene)diphenol |
FT-0634740 |
SCHEMBL45826 |
9,9-bis(4'-hydroxyphenyl)fluorene |
9,9-bis(4-hydroxyphenyl)-9h-fluorene |
9,9-bis-(4-hydroxyphenyl)-fluorene |
9,9-bis[4-hydroxyphenyl]fluorene |
9,9-bis(4-hydroxyphenyl) fluorene |
9,9-bis (4-hydroxyphenyl)-fluorene |
9,9-bis (4-hydroxyphenyl) fluorene |
fluorene-9-bipheno |
Q-200568 |
fluorene-9-biphenol |
fluouene-9-bisphenol |
Q-101172 |
B4834 |
bisphenol fl, analytical standard |
mfcd00191392 |
9,9'-bis(4-hydroxyphenyl)fluorene |
AC-4883 |
4,4'-(9-fluorenylidene)diphenol, 98% |
bp_13 |
BCP26097 |
9,9-bis(4-hydroxyphenyl)fluorene;9,9-bis(4-hydroxyphenyl)fluorene |
Q29460410 |
bisphenol fl |
9,9-bis(4-hydroxyphenyl)fluorene (purified by sublimation) |
AS-13055 |
AMY043 |
OL10063 |
CS-W009810 |
SB66591 |
Excerpt | Reference | Relevance |
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" In the present study, we checked the toxic effects of BHPF on porcine oocyte maturation which is derived from COCs in vitro culture." | ( The toxic effects of Fluorene-9-bisphenol on porcine oocyte in vitro maturation. Chen, F; Ding, Z; Duan, Z; Huo, L; Jiao, X; Meng, F; Miao, Y; Wang, Y; Wu, D; Zhang, S; Zhang, X, 2020) | 0.56 |
" Several epidemiological and animal studies have demonstrated the correlation between pollutants and gastrointestinal diseases, but detailed molecular mechanisms responsible for adverse effects of environmental pollutants on UC are still unknown." | ( Analyzing the synergistic adverse effects of BPA and its substitute, BHPF, on ulcerative colitis through comparative metabolomics. Chan, TF; Huang, X; Lai, KP; Li, R; Lin, X; Yin, F, 2022) | 0.72 |
Excerpt | Relevance | Reference |
---|---|---|
" Collectively, this study provides the full understanding of the environmental impact of BHPF and its toxicity on living organisms, highlighting a substantial and generalized ongoing dose-response relationship with great implications for the usage and risk assessment of BHPF." | ( The possible hormetic effects of fluorene-9-bisphenol on regulating hypothalamic-pituitary-thyroid axis in zebrafish. Dang, J; Jin, M; Li, P; Liu, K; Paudel, YN; Sun, C; Wang, B; Wang, L; Wang, X, 2021) | 0.62 |
" The absorbance decreased significantly over time following treatment with each endocrine disruptor at the concentration confirmed by the dose-response analysis." | ( Effects of polycyclic aromatic hydrocarbons on the proliferation and differentiation of placental cells. Choi, SK; Jo, HG; Jo, YS; Kim, AY; Kim, WJ; Ko, HS, 2022) | 0.72 |
Role | Description |
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anti-estrogen | A drug which acts to reduce estrogenic activity in the body, either by reducing the amount of estrogen or by reducing the activity of whatever estrogen is present. |
[role 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] |
Class | Description |
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fluorenes | An ortho-fused polycyclic arene in which the skeleton is composed of two benzene rings ortho-fused to cyclopentane. |
polyphenol | Members of the class of phenols that contain 2 or more benzene rings each of which is substituted by at least one hydroxy group. |
[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 | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
acetylcholinesterase | Homo sapiens (human) | Potency | 64.6367 | 0.0025 | 41.7960 | 15,848.9004 | AID1347395; AID1347397 |
hypoxia-inducible factor 1 alpha subunit | Homo sapiens (human) | Potency | 54.9410 | 3.1890 | 29.8841 | 59.4836 | AID1224846; AID1224894 |
RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 68.5896 | 0.0060 | 38.0041 | 19,952.5996 | AID1159521; AID1159523 |
GLI family zinc finger 3 | Homo sapiens (human) | Potency | 32.9384 | 0.0007 | 14.5928 | 83.7951 | AID1259369; AID1259392 |
AR protein | Homo sapiens (human) | Potency | 23.2253 | 0.0002 | 21.2231 | 8,912.5098 | AID1259243; AID1259247; AID588515; AID743035; AID743036; AID743042; AID743054; AID743063 |
caspase 7, apoptosis-related cysteine protease | Homo sapiens (human) | Potency | 68.5896 | 0.0133 | 26.9810 | 70.7614 | AID1346978 |
estrogen receptor 2 (ER beta) | Homo sapiens (human) | Potency | 72.7742 | 0.0006 | 57.9133 | 22,387.1992 | AID1259377; AID1259378 |
nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 26.7745 | 0.0010 | 22.6508 | 76.6163 | AID1224838; AID1224839; AID1224893 |
progesterone receptor | Homo sapiens (human) | Potency | 57.8067 | 0.0004 | 17.9460 | 75.1148 | AID1346784; AID1346795 |
glucocorticoid receptor [Homo sapiens] | Homo sapiens (human) | Potency | 54.5862 | 0.0002 | 14.3764 | 60.0339 | AID588533; AID720691; AID720692; AID720719 |
retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 62.1115 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552; AID1159553; AID1159555 |
retinoid X nuclear receptor alpha | Homo sapiens (human) | Potency | 55.5682 | 0.0008 | 17.5051 | 59.3239 | AID1159527; AID1159531; AID588546 |
estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 68.5896 | 0.0015 | 30.6073 | 15,848.9004 | AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403 |
farnesoid X nuclear receptor | Homo sapiens (human) | Potency | 33.2397 | 0.3758 | 27.4851 | 61.6524 | AID588526; AID743217; AID743220; AID743239 |
pregnane X nuclear receptor | Homo sapiens (human) | Potency | 34.5024 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982; AID720659 |
estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 31.9969 | 0.0002 | 29.3054 | 16,493.5996 | AID1259244; AID588513; AID743069; AID743075; AID743077; AID743078; AID743079; AID743080; AID743091 |
peroxisome proliferator-activated receptor delta | Homo sapiens (human) | Potency | 42.5160 | 0.0010 | 24.5048 | 61.6448 | AID743212; AID743215; AID743227 |
peroxisome proliferator activated receptor gamma | Homo sapiens (human) | Potency | 52.8344 | 0.0010 | 19.4141 | 70.9645 | AID588536; AID743094; AID743140; AID743191 |
vitamin D (1,25- dihydroxyvitamin D3) receptor | Homo sapiens (human) | Potency | 33.9832 | 0.0237 | 23.2282 | 63.5986 | AID743223; AID743241 |
caspase-3 | Homo sapiens (human) | Potency | 68.5896 | 0.0133 | 26.9810 | 70.7614 | AID1346978 |
cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a | Homo sapiens (human) | Potency | 76.9588 | 0.0017 | 23.8393 | 78.1014 | AID743083 |
thyroid stimulating hormone receptor | Homo sapiens (human) | Potency | 54.4827 | 0.0016 | 28.0151 | 77.1139 | AID1224843; AID1224895 |
activating transcription factor 6 | Homo sapiens (human) | Potency | 54.9410 | 0.1434 | 27.6121 | 59.8106 | AID1159516; AID1159519 |
nuclear factor of kappa light polypeptide gene enhancer in B-cells 1 (p105), isoform CRA_a | Homo sapiens (human) | Potency | 54.9410 | 19.7391 | 45.9784 | 64.9432 | AID1159509; AID1159518 |
v-jun sarcoma virus 17 oncogene homolog (avian) | Homo sapiens (human) | Potency | 50.1448 | 0.0578 | 21.1097 | 61.2679 | AID1159526; AID1159528 |
Histone H2A.x | Cricetulus griseus (Chinese hamster) | Potency | 67.3124 | 0.0391 | 47.5451 | 146.8240 | AID1224896 |
thyroid hormone receptor beta isoform a | Homo sapiens (human) | Potency | 42.2090 | 0.0100 | 39.5371 | 1,122.0200 | AID588545; AID588547 |
thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 15.3553 | 0.0003 | 23.4451 | 159.6830 | AID743065; AID743067 |
heat shock protein beta-1 | Homo sapiens (human) | Potency | 28.2689 | 0.0420 | 27.3789 | 61.6448 | AID743210; AID743228 |
nuclear factor NF-kappa-B p105 subunit isoform 1 | Homo sapiens (human) | Potency | 50.1187 | 4.4668 | 24.8329 | 44.6684 | AID651749 |
nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 52.1324 | 0.0006 | 27.2152 | 1,122.0200 | AID651741; AID743202 |
Voltage-dependent calcium channel gamma-2 subunit | Mus musculus (house mouse) | Potency | 1.7229 | 0.0015 | 57.7890 | 15,848.9004 | AID1259244 |
Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 54.8211 | 0.0023 | 19.5956 | 74.0614 | AID651631; AID651743; AID720552 |
Glutamate receptor 2 | Rattus norvegicus (Norway rat) | Potency | 1.7229 | 0.0015 | 51.7393 | 15,848.9004 | AID1259244 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID46664 | Fraction of total radioactivity [86Rb] remaining with the compound at a concentration of 0 uM in presence of DMSO (0.02% v/v) in COS-7 | 1998 | Journal of medicinal chemistry, Oct-22, Volume: 41, Issue:22 | Bisphenols that stimulate cells to release alkali metal cations: a structure-activity study. |
AID46670 | Fraction of total radioactivity [86Rb] remaining with the compound at a concentration of 10 uM in COS-7 cells | 1998 | Journal of medicinal chemistry, Oct-22, Volume: 41, Issue:22 | Bisphenols that stimulate cells to release alkali metal cations: a structure-activity study. |
AID46666 | Fraction of total radioactivity [86Rb] remaining with the compound at a concentration of 0.01 uM in COS-7 cells | 1998 | Journal of medicinal chemistry, Oct-22, Volume: 41, Issue:22 | Bisphenols that stimulate cells to release alkali metal cations: a structure-activity study. |
AID46668 | Fraction of total radioactivity [86Rb] remaining with the compound at a concentration of 0.1 uM in COS-7 cells and value | 1998 | Journal of medicinal chemistry, Oct-22, Volume: 41, Issue:22 | Bisphenols that stimulate cells to release alkali metal cations: a structure-activity study. |
AID46669 | Fraction of total radioactivity [86Rb] remaining with the compound at a concentration of 1 uM in COS-7 cells | 1998 | Journal of medicinal chemistry, Oct-22, Volume: 41, Issue:22 | Bisphenols that stimulate cells to release alkali metal cations: a structure-activity study. |
AID46663 | Fraction of total radioactivity [86Rb] remaining with the compound at a concentration of 0 uM in COS-7 cells | 1998 | Journal of medicinal chemistry, Oct-22, Volume: 41, Issue:22 | Bisphenols that stimulate cells to release alkali metal cations: a structure-activity study. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 1 (5.26) | 18.2507 |
2000's | 0 (0.00) | 29.6817 |
2010's | 3 (15.79) | 24.3611 |
2020's | 15 (78.95) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
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.
| This Compound (23.57) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 1 (5.26%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 18 (94.74%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |