2,2'-Methylenebis(ethyl-6-tert-butylphenol), also known as MBP, is a synthetic antioxidant commonly used in a variety of industrial applications. It is typically synthesized through the reaction of ethyl-6-tert-butylphenol with formaldehyde under acidic conditions. MBP exhibits strong antioxidant properties, effectively scavenging free radicals and inhibiting oxidation processes, making it crucial in preventing degradation of materials exposed to oxidative stress. It is commonly incorporated into polymers, plastics, rubber, and lubricants, to extend their shelf life and enhance their performance. The compound has been studied extensively for its potential health effects, particularly its role in endocrine disruption. Some studies have shown that MBP may interfere with hormone signaling pathways, raising concerns about its potential to disrupt reproductive development. However, further research is needed to fully understand the specific mechanisms and health implications of MBP exposure.'
ID Source | ID |
---|---|
PubMed CID | 6928 |
CHEMBL ID | 3182523 |
SCHEMBL ID | 27533 |
MeSH ID | M0096607 |
Synonym |
---|
AKOS015839099 |
usaf cy-6 |
plastanox 425 |
2,2'-methylenebis(4-ethyl-6-tert-butylphenol) |
chemanox 22 |
phenol,2'-methylenebis[6-tert-butyl-4-ethyl- |
88-24-4 |
antioxidant 425 |
plastanox 425 antioxidant |
ao 425 |
wln: 1x1&1&r bq f2 c1r bq d2 cx1&1&1 |
2,2'-methylenebis(6-tert-butyl-4-ethylphenol) |
bis(2-hydroxy-3-tert-butyl-5-ethylphenyl)methane |
nsc7782 |
phenol,2'-methylenebis[6-(1,1-dimethylethyl)-4-ethyl- |
nsc-7782 |
phenol, 2,2'-methylenebis[6-(1,1-dimethylethyl)-4-ethyl- |
phenol, 2,2'-methylenebis[6-tert-butyl-4-ethyl- |
2,2'-methylenebis(ethyl-6-tert-butylphenol) |
agidol 7 |
nsc 7782 |
phenol, 2,2'-methylenebis(6-tert-butyl-4-ethyl- |
cyanox 425 |
2,2-methylenebis(4-ethyl-6-t-butylphenol) |
einecs 201-814-0 |
ccris 7788 |
hsdb 5257 |
ai3-25275 |
yoshinox 425 |
brn 2016207 |
antage w 500 |
6,6'-di-tert-butyl-4,4'-diethyl-2,2'-methylenediphenol |
nocrac ns 5 |
phenol, 2,2'-methylenebis(6-(1,1-dimethylethyl)-4-ethyl- |
2,2'-methylenebis(6-(1,1-dimethylethyl)-4-ethylphenol) |
bis(3-tert-butyl-5-ethyl-2-hydroxyphenyl)methane |
c25h36o2 |
2,2'-methylenebis(6-t-butyl-4-ethylphenol) |
2,2'-methanediylbis(6-tert-butyl-4-ethylphenol) |
2-tert-butyl-6-[(3-tert-butyl-5-ethyl-2-hydroxyphenyl)methyl]-4-ethylphenol |
3,3'-di-tert-butyl-5,5'-diethyl-2,2'-dihydroxydiphenylmethane |
M0215 |
2-tert-butyl-4-ethyl-6-[(2-hydroxyphenyl)methyl]phenol |
A842508 |
2,2-methylenebis(4-ethyl-6-tert-butylphenol) |
NCGC00257360-01 |
dtxsid7038864 , |
cas-88-24-4 |
tox21_303358 |
dtxcid5018864 |
rzw97f6cts , |
4-06-00-06806 (beilstein handbook reference) |
unii-rzw97f6cts |
2,2'-methylenebis(6-(tert-butyl)-4-ethylphenol) |
FT-0609308 |
2,2'-methylene-bis-(4-ethyl-6-tert.butylphenol) |
2,2'-methylene-bis(4-ethyl-6-tert-butyl phenol) |
2,2'-methylenebis (6-tert-butyl-4-ethylphenol) |
2,2'-methylene-bis(4-ethyl-6-tertiarybutyl phenol) |
6,6'-methylenebis(2-(tert-butyl)-4-ethylphenol) |
SCHEMBL27533 |
methylenebis(4-ethyl-6-tert-butylphenol), 2-2'- |
2,2'-methylenebis(6-t-butyl-4-ethylphenol) [hsdb] |
2,2'-methylenebis[6-(tert-butyl)-4-ethylphenol] |
2,2'-methylenebis(4-ethyl-6-t-butylphenol) |
W-100409 |
2,2'-methylene-bis-(4-ethyl-6-tert-butylphenol) |
2,2'-methylenebis(6-tert-butyl-4-ethylphenol), certified reference material, tracecert(r) |
CHEMBL3182523 , |
2,2'-methylene-bis(4-ethyl-6-t-butyl) phenol |
phenol, 2,2'-methylenebis[4-ethyl-6(1,1-dimethylethyl)]- |
mfcd00026296 |
DS-13037 |
D71074 |
Q27288370 |
2,2'-methylene-bis(4-ethyl-6-tert-butylphenol) 100 microg/ml in acetonitrile |
bdbm50522652 |
2,2'-methylene-bis(4-ethyl-6-tert-butylphenol) |
2,2/'-methylene bis(6-tert-butyl-4-ethylphenol) |
CS-0152543 |
Excerpt | Reference | Relevance |
---|---|---|
" In acute toxicity test, the LD50 values were estimated to be greater than 10 g/kg BW by oral and intraperitoneal administration in each sex." | ( Toxicity studies of a synthetic antioxidant, 2,2'-methylenebis (4-ethyl-6-tert-butylphenol) in rats. 1. Acute and subchronic toxicity. Aida, Y; Hasegawa, R; Kurokawa, Y; Momma, J; Naitoh, K; Suzuki, S; Takada, K; Takagi, A; Tobe, M, 1992) | 0.28 |
Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
hypoxia-inducible factor 1 alpha subunit | Homo sapiens (human) | Potency | 12.1231 | 3.1890 | 29.8841 | 59.4836 | AID1224846; AID1224894 |
RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 18.6171 | 0.0060 | 38.0041 | 19,952.5996 | AID1159521; AID1159523 |
SMAD family member 2 | Homo sapiens (human) | Potency | 48.9722 | 0.1737 | 34.3047 | 61.8120 | AID1346924 |
SMAD family member 3 | Homo sapiens (human) | Potency | 48.9722 | 0.1737 | 34.3047 | 61.8120 | AID1346924 |
GLI family zinc finger 3 | Homo sapiens (human) | Potency | 31.1861 | 0.0007 | 14.5928 | 83.7951 | AID1259368; AID1259369; AID1259392 |
AR protein | Homo sapiens (human) | Potency | 31.9423 | 0.0002 | 21.2231 | 8,912.5098 | AID1259243; AID1259247; AID743035; AID743036; AID743042; AID743053; 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 | 29.5273 | 0.0006 | 57.9133 | 22,387.1992 | AID1259377; AID1259378; AID1259394 |
nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 30.3736 | 0.0010 | 22.6508 | 76.6163 | AID1224838; AID1224839; AID1224893 |
progesterone receptor | Homo sapiens (human) | Potency | 44.2183 | 0.0004 | 17.9460 | 75.1148 | AID1346784; AID1346795 |
glucocorticoid receptor [Homo sapiens] | Homo sapiens (human) | Potency | 15.7109 | 0.0002 | 14.3764 | 60.0339 | AID720691; AID720692; AID720719 |
retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 26.3162 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552; AID1159553; AID1159555 |
retinoid X nuclear receptor alpha | Homo sapiens (human) | Potency | 34.8997 | 0.0008 | 17.5051 | 59.3239 | AID1159527; AID1159531 |
estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 31.5387 | 0.0015 | 30.6073 | 15,848.9004 | AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403 |
farnesoid X nuclear receptor | Homo sapiens (human) | Potency | 26.0930 | 0.3758 | 27.4851 | 61.6524 | AID743217; AID743220; AID743239 |
pregnane X nuclear receptor | Homo sapiens (human) | Potency | 0.6859 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982 |
estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 30.1702 | 0.0002 | 29.3054 | 16,493.5996 | AID1259244; AID1259248; AID1259383; AID743069; AID743075; AID743077; AID743078; AID743079; AID743080; AID743091 |
peroxisome proliferator-activated receptor delta | Homo sapiens (human) | Potency | 22.1548 | 0.0010 | 24.5048 | 61.6448 | AID743212; AID743215; AID743227 |
peroxisome proliferator activated receptor gamma | Homo sapiens (human) | Potency | 28.0200 | 0.0010 | 19.4141 | 70.9645 | AID743094; AID743140; AID743191 |
vitamin D (1,25- dihydroxyvitamin D3) receptor | Homo sapiens (human) | Potency | 17.4529 | 0.0237 | 23.2282 | 63.5986 | AID743222; 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 | 30.6379 | 0.0017 | 23.8393 | 78.1014 | AID743083 |
activating transcription factor 6 | Homo sapiens (human) | Potency | 30.6341 | 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 | 25.0532 | 19.7391 | 45.9784 | 64.9432 | AID1159509; AID1159518 |
v-jun sarcoma virus 17 oncogene homolog (avian) | Homo sapiens (human) | Potency | 14.5096 | 0.0578 | 21.1097 | 61.2679 | AID1159526; AID1159528 |
Histone H2A.x | Cricetulus griseus (Chinese hamster) | Potency | 49.5269 | 0.0391 | 47.5451 | 146.8240 | AID1224845; AID1224896 |
Caspase-7 | Cricetulus griseus (Chinese hamster) | Potency | 54.4827 | 0.0067 | 23.4960 | 68.5896 | AID1346980 |
caspase-3 | Cricetulus griseus (Chinese hamster) | Potency | 54.4827 | 0.0067 | 23.4960 | 68.5896 | AID1346980 |
thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 6.3569 | 0.0003 | 23.4451 | 159.6830 | AID743065; AID743067 |
heat shock protein beta-1 | Homo sapiens (human) | Potency | 17.2918 | 0.0420 | 27.3789 | 61.6448 | AID743210; AID743228 |
nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 23.4515 | 0.0006 | 27.2152 | 1,122.0200 | AID743202; AID743219 |
Voltage-dependent calcium channel gamma-2 subunit | Mus musculus (house mouse) | Potency | 30.6379 | 0.0015 | 57.7890 | 15,848.9004 | AID1259244 |
Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 19.7516 | 0.0023 | 19.5956 | 74.0614 | AID651631; AID720552 |
Glutamate receptor 2 | Rattus norvegicus (Norway rat) | Potency | 30.6379 | 0.0015 | 51.7393 | 15,848.9004 | AID1259244 |
ATPase family AAA domain-containing protein 5 | Homo sapiens (human) | Potency | 27.8401 | 0.0119 | 17.9420 | 71.5630 | AID651632; AID720516 |
Ataxin-2 | Homo sapiens (human) | Potency | 27.3060 | 0.0119 | 12.2221 | 68.7989 | AID651632 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
Endoplasmic reticulum chaperone BiP | Homo sapiens (human) | IC50 (µMol) | 100.0000 | 0.8000 | 7.0250 | 9.1000 | AID1590351 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1590351 | Inhibition of GRP78 (26 to 636 residues) (unknown origin) expressed in Escherichia coli BL21 DE3 cells pre-incubated for 10 mins before FITC-NRLLLTG fluorescent peptide addition in presence of 20 uM ADP followed by further incubation for 2 hrs by fluoresc | 2019 | Bioorganic & medicinal chemistry letters, 07-15, Volume: 29, Issue:14 | A high throughput substrate binding assay reveals hexachlorophene as an inhibitor of the ER-resident HSP70 chaperone GRP78. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 4 (50.00) | 18.7374 |
1990's | 2 (25.00) | 18.2507 |
2000's | 0 (0.00) | 29.6817 |
2010's | 1 (12.50) | 24.3611 |
2020's | 1 (12.50) | 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 (21.36) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 0 (0.00%) | 6.00% |
Case Studies | 1 (11.11%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 8 (88.89%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |