4,4'-Thiobis(6-tert-butyl-3-cresol), also known as Thiobis(6-tert-butyl-m-cresol) or TBBC, is a hindered phenol antioxidant. It is synthesized by the reaction of p-cresol with sulfur monochloride in the presence of a catalyst. TBBC is a white to off-white crystalline solid that is insoluble in water but soluble in organic solvents. It is used as a stabilizer in polymers, rubber, and other materials. It is effective in preventing oxidation and degradation caused by exposure to heat, light, and oxygen. TBBC has also been studied for its potential as an anti-inflammatory and antioxidant agent. It is a potent scavenger of free radicals and has been shown to protect cells from damage caused by oxidative stress. TBBC is also an effective inhibitor of the enzyme cyclooxygenase-2, which is involved in the production of prostaglandins, which are involved in inflammation.'
4,4'-thiobis(6-tert-butyl-3-cresol): structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 7308 |
| CHEMBL ID | 1526319 |
| SCHEMBL ID | 39505 |
| MeSH ID | M0119394 |
| Synonym |
|---|
| 5-t-butyl-4-hydroxy-2-methyl-phenyl sulfide |
| BIDD:ER0693 |
| m-cresol, 4,4'-thiobis[6-tert-butyl- |
| phenol, 4,4'-thiobis[2-(1,1-dimethylethyl)-5-methyl- |
| 4,4'-thiobis(3-methyl-6-tert-butylphenol) |
| bis(3-tert-butyl-4-hydroxy-6-methylphenyl) sulfide |
| m-cresol,4'-thiobis(6-tert-butyl- |
| nsc-35388 |
| santonox bm |
| thioalkophene bm-4 |
| sumilizer wx-r |
| m-cresol,4'-thiobis[6-tert-butyl- |
| 4,4'-thiobis[6-tert-butyl-m-cresol] |
| santowhite crystals |
| santonox |
| yoshinox sr |
| thioalkofen mbch |
| 4,4'-thiobis(6-tert-butyl-m-cresol) |
| thioalkofen bmch |
| disperse mb-61 |
| sumilizer wx |
| nsc35388 |
| thioalkofen bm 4 |
| 96-69-5 |
| bis(4-hydroxy-5-tert-butyl-2-methylphenyl) sulfide |
| 4,4'-thiobis(2-tert-butyl-5-methylphenol) |
| wln: 1x1&1&r bq d1 esr dq b1 ex1&1&1 |
| 4,4'-thiobis(6-tert-butyl-3-methylphenol) |
| usaf b-15 |
| 1,1'-thiobis(2-methyl-4-hydroxy-5-tert-butylbenzene) |
| phenol,4'-thiobis[2-(1,1-dimethylethyl)-5-methyl- |
| 4,4'-thiobis[2-(1,1-dimethylethyl)-5-methylphenol] |
| santonox r |
| 4,4'-thiobis(6-t-butyl-m-cresol) |
| brn 1147776 |
| hsdb 5304 |
| nsc 35388 |
| 5-tert-butyl-4-hydroxy-2-methylphenyl sulfide |
| c22h30o2s |
| nocrac 300 |
| einecs 202-525-2 |
| ccris 4917 |
| antioxidant tmb 6 |
| 6,6'-di-tert-butyl-4,4'-thiodi-m-cresol |
| 4,4'-thiobis(2-(1,1-dimethylethyl)-5-methylphenol) |
| phenol, 4,4'-thiobis(2-(1,1-dimethylethyl)-5-methyl- |
| yoshinox s |
| antage crystal |
| antioxidant ao |
| 4,4'-thiobis(6-tert-butyl-3-cresol) |
| nonflex bps |
| 4, {4'-thiobis[6-tert-butyl-m-cresol]} |
| 4, 4'-thiobis(3-methyl-6-tert-butylphenol) |
| 4, 4'-thiobis(6-tert-butyl-m-cresol) |
| 4, 4'-thiobis(6-tert-butyl-3-methylphenol) |
| 4, 4'-thiobis(2-tert-butyl-5-methylphenol) |
| phenol, {4,4'-thiobis[2-(1,1-dimethylethyl)-5-methyl-} |
| m-cresol, 4,4'-thiobis(6-tert-butyl- |
| 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methyl-phenyl)sulfanyl-5-methyl-phenol |
| m-cresol, 4, {4'-thiobis[6-tert-butyl-} |
| 1, 1'-thiobis(2-methyl-4-hydroxy-5-tert-butylbenzene) |
| NCGC00091503-01 |
| 4,4-thiobis(6-tert-butyl-m-cresol) |
| NCGC00091503-02 |
| 4,4-thiobis(6-t-butyl-m-cresol) |
| OPREA1_700795 |
| AKOS001606677 |
| 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol |
| bis(5-tert-butyl-4-hydroxy-2-methylphenyl) sulfide |
| T0196 |
| NCGC00091503-03 |
| NCGC00091503-04 |
| 2-tert-butyl-4-[(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl]-5-methylphenol |
| 3ca5g9822v , |
| ec 202-525-2 |
| 4-06-00-06043 (beilstein handbook reference) |
| unii-3ca5g9822v |
| cas-96-69-5 |
| tox21_201022 |
| dtxsid4021341 , |
| dtxcid301341 |
| NCGC00258575-01 |
| 57062-46-1 |
| ST029248 , |
| 2-(tert-butyl)-4-[5-(tert-butyl)-4-hydroxy-2-methylphenylthio]-5-methylphenol |
| FT-0631492 |
| 4,4'-thiobis(2-(tert-butyl)-5-methylphenol) |
| thiobis(6-tert-butyl-m-cresol), 4,4'- |
| lowinox 44s36 |
| 4,4-thio-bis-2-tertbutyl-5-methylphenol |
| santonox [hsdb] |
| ultranox 236 |
| AB01321991-02 |
| SCHEMBL39505 |
| 4,4' thiobis(6-tert-butyl-m cresol) |
| 4,4'-thiobis(6-tertiarybutyl-m-cresol) |
| 4,4'-thiobis-(6-t-butyl-3-methylphenol) |
| 4,4'-thiobis (2-(tert-butyl)-5-methylphenol) |
| 4,4'-thio-bis-(6-tert-butyl-m-cresol) |
| W-100136 |
| CHEMBL1526319 |
| 4,4'-thiobis(3-methyl-6-t-butylphenol) |
| 4,4-thiobis-(6-t-butyl-3-methyl-phenol) |
| 5-t-butyl-4-hydroxy-2-methylphenyl sulfide |
| 3-tert-butyl-4-hydroxy-6-methylphenyl sulfide |
| 4,4'-thio-bis (2-t-butyl-5-methylphenol) |
| mfcd00026287 |
| SR-01000408145-1 |
| sr-01000408145 |
| 4,4'-thio-bis(3-methyl-6-tert-butylphenol) |
| NCGC00091503-05 |
| bp_20 |
| 4,4'-sulfanediylbis(2-tert-butyl-5-methylphenol) |
| DS-5625 |
| 4,4'-thio-bis(6-tert-butyl-3-methylphenol) |
| 4,4'-thiobis(6-tert-butyl-m-cresol); 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol; |
| 4,4'-thio-bis(6-t-butyl-3-methyl phenol) |
| Q20965073 |
| A858679 |
| 4,4'-thio-bis(6-tert-butyl-m-methyl phenol) |
| CS-0153284 |
| ?4,4'-thiobis(6-tert-butyl-m-cresol) |
| Excerpt | Reference | Relevance |
|---|---|---|
| "Age-related changes in glucuronidation may potentially lead to a decrease in excretion of reactive compounds, resulting in enhanced toxic effects." | ( The effect of age on the glucuronidation and toxicity of 4,4'-thiobis(6-t-butyl-m-cresol). Birnbaum, LS; Borghoff, SJ; Stefanski, SA, 1988) | 0.27 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " Oral treatment showed a dose-related decrease in the rate of absorption due to a dose-related increase in retention time in the stomach." | ( Disposition of 4,4'-thiobis(6-t-butyl-m-cresol) in rats. Birnbaum, LS; Eastin, WC; Johnson, L; Matthews, HB, ) | 0.13 |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, TYROSYL-DNA PHOSPHODIESTERASE | Homo sapiens (human) | Potency | 70.7946 | 0.0040 | 23.8416 | 100.0000 | AID485290 |
| interleukin 8 | Homo sapiens (human) | Potency | 33.4915 | 0.0473 | 49.4806 | 74.9780 | AID651758 |
| acetylcholinesterase | Homo sapiens (human) | Potency | 28.2115 | 0.0025 | 41.7960 | 15,848.9004 | AID1347397 |
| 15-lipoxygenase, partial | Homo sapiens (human) | Potency | 10.0000 | 0.0126 | 10.6917 | 88.5700 | AID887 |
| pregnane X receptor | Rattus norvegicus (Norway rat) | Potency | 52.2759 | 0.0251 | 27.9203 | 501.1870 | AID651751 |
| hypoxia-inducible factor 1 alpha subunit | Homo sapiens (human) | Potency | 13.3774 | 3.1890 | 29.8841 | 59.4836 | AID1224846; AID1224894 |
| RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 3.9290 | 0.0060 | 38.0041 | 19,952.5996 | AID1159521; AID1159523 |
| SMAD family member 2 | Homo sapiens (human) | Potency | 61.5242 | 0.1737 | 34.3047 | 61.8120 | AID1346859; AID1346924; AID1347035 |
| SMAD family member 3 | Homo sapiens (human) | Potency | 61.5242 | 0.1737 | 34.3047 | 61.8120 | AID1346859; AID1346924; AID1347035 |
| GLI family zinc finger 3 | Homo sapiens (human) | Potency | 11.6059 | 0.0007 | 14.5928 | 83.7951 | AID1259368; AID1259369; AID1259392 |
| AR protein | Homo sapiens (human) | Potency | 31.3458 | 0.0002 | 21.2231 | 8,912.5098 | AID1259243; AID1259247; AID588515; AID588516; AID743035; AID743036; AID743042; AID743053; AID743054; AID743063 |
| caspase 7, apoptosis-related cysteine protease | Homo sapiens (human) | Potency | 30.5756 | 0.0133 | 26.9810 | 70.7614 | AID1346978 |
| aldehyde dehydrogenase 1 family, member A1 | Homo sapiens (human) | Potency | 39.8107 | 0.0112 | 12.4002 | 100.0000 | AID1030 |
| hypoxia-inducible factor 1, alpha subunit (basic helix-loop-helix transcription factor) | Homo sapiens (human) | Potency | 25.1189 | 0.0013 | 7.7625 | 44.6684 | AID2120 |
| thyroid stimulating hormone receptor | Homo sapiens (human) | Potency | 39.8107 | 0.0013 | 18.0743 | 39.8107 | AID926; AID938 |
| estrogen receptor 2 (ER beta) | Homo sapiens (human) | Potency | 34.2381 | 0.0006 | 57.9133 | 22,387.1992 | AID1259377; AID1259378; AID1259394 |
| nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 29.5230 | 0.0010 | 22.6508 | 76.6163 | AID1224838; AID1224839; AID1224893 |
| progesterone receptor | Homo sapiens (human) | Potency | 38.7218 | 0.0004 | 17.9460 | 75.1148 | AID1346784; AID1346795; AID1347036 |
| glucocorticoid receptor [Homo sapiens] | Homo sapiens (human) | Potency | 29.0587 | 0.0002 | 14.3764 | 60.0339 | AID588533; AID720691; AID720692; AID720719 |
| retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 6.7087 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552; AID1159553; AID1159555 |
| retinoid X nuclear receptor alpha | Homo sapiens (human) | Potency | 28.5644 | 0.0008 | 17.5051 | 59.3239 | AID1159527; AID588544; AID588546 |
| estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 18.7852 | 0.0015 | 30.6073 | 15,848.9004 | AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403 |
| farnesoid X nuclear receptor | Homo sapiens (human) | Potency | 19.4735 | 0.3758 | 27.4851 | 61.6524 | AID588526; AID588527; AID743217; AID743220; AID743239 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 9.9158 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982; AID720659 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 38.1417 | 0.0002 | 29.3054 | 16,493.5996 | AID1259244; AID1259248; AID1259383; AID588513; AID743069; AID743075; AID743077; AID743078; AID743079; AID743080; AID743091 |
| peroxisome proliferator-activated receptor delta | Homo sapiens (human) | Potency | 21.0299 | 0.0010 | 24.5048 | 61.6448 | AID588534; AID588535; AID743212; AID743215; AID743227 |
| peroxisome proliferator activated receptor gamma | Homo sapiens (human) | Potency | 39.8500 | 0.0010 | 19.4141 | 70.9645 | AID588536; AID588537; AID743094; AID743140; AID743191 |
| vitamin D (1,25- dihydroxyvitamin D3) receptor | Homo sapiens (human) | Potency | 24.1552 | 0.0237 | 23.2282 | 63.5986 | AID588541; AID743222; AID743223; AID743241 |
| caspase-3 | Homo sapiens (human) | Potency | 30.5756 | 0.0133 | 26.9810 | 70.7614 | AID1346978 |
| aryl hydrocarbon receptor | Homo sapiens (human) | Potency | 54.3719 | 0.0007 | 23.0674 | 1,258.9301 | AID743122 |
| cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a | Homo sapiens (human) | Potency | 13.6576 | 0.0017 | 23.8393 | 78.1014 | AID743083 |
| thyroid stimulating hormone receptor | Homo sapiens (human) | Potency | 39.9281 | 0.0016 | 28.0151 | 77.1139 | AID1224843; AID1224895; AID1259385; AID1259395 |
| activating transcription factor 6 | Homo sapiens (human) | Potency | 44.4139 | 0.1434 | 27.6121 | 59.8106 | AID1159516; AID1159519 |
| thyrotropin-releasing hormone receptor | Homo sapiens (human) | Potency | 30.0922 | 0.1549 | 17.8702 | 43.6557 | AID1346877 |
| nuclear factor of kappa light polypeptide gene enhancer in B-cells 1 (p105), isoform CRA_a | Homo sapiens (human) | Potency | 24.1134 | 19.7391 | 45.9784 | 64.9432 | AID1159509; AID1159518 |
| v-jun sarcoma virus 17 oncogene homolog (avian) | Homo sapiens (human) | Potency | 16.1367 | 0.0578 | 21.1097 | 61.2679 | AID1159526; AID1159528 |
| cellular tumor antigen p53 isoform a | Homo sapiens (human) | Potency | 15.8489 | 0.3162 | 12.4435 | 31.6228 | AID902 |
| thyroid hormone receptor beta isoform a | Homo sapiens (human) | Potency | 24.4274 | 0.0100 | 39.5371 | 1,122.0200 | AID588545; AID588547 |
| potassium voltage-gated channel subfamily H member 2 isoform d | Homo sapiens (human) | Potency | 39.8107 | 0.0178 | 9.6374 | 44.6684 | AID588834 |
| thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 2.0701 | 0.0003 | 23.4451 | 159.6830 | AID743065; AID743066; AID743067 |
| heat shock protein beta-1 | Homo sapiens (human) | Potency | 21.5229 | 0.0420 | 27.3789 | 61.6448 | AID743210; AID743228 |
| mitogen-activated protein kinase 1 | Homo sapiens (human) | Potency | 0.0631 | 0.0398 | 16.7842 | 39.8107 | AID995 |
| nuclear factor NF-kappa-B p105 subunit isoform 1 | Homo sapiens (human) | Potency | 33.9972 | 4.4668 | 24.8329 | 44.6684 | AID651749 |
| nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 36.7035 | 0.0006 | 27.2152 | 1,122.0200 | AID651741; AID720636; AID743202; AID743219 |
| nuclear receptor ROR-gamma isoform 1 | Mus musculus (house mouse) | Potency | 14.9763 | 0.0079 | 8.2332 | 1,122.0200 | AID2546; AID2551 |
| survival motor neuron protein isoform d | Homo sapiens (human) | Potency | 35.4813 | 0.1259 | 12.2344 | 35.4813 | AID1458 |
| cytochrome P450 3A4 isoform 1 | Homo sapiens (human) | Potency | 3.9811 | 0.0316 | 10.2792 | 39.8107 | AID884; AID885 |
| lethal factor (plasmid) | Bacillus anthracis str. A2012 | Potency | 15.8489 | 0.0200 | 10.7869 | 31.6228 | AID912 |
| Gamma-aminobutyric acid receptor subunit pi | Rattus norvegicus (Norway rat) | Potency | 3.9811 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Voltage-dependent calcium channel gamma-2 subunit | Mus musculus (house mouse) | Potency | 30.5756 | 0.0015 | 57.7890 | 15,848.9004 | AID1259244 |
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 26.7919 | 0.0023 | 19.5956 | 74.0614 | AID651631; AID651743; AID720552 |
| Gamma-aminobutyric acid receptor subunit beta-1 | Rattus norvegicus (Norway rat) | Potency | 3.9811 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit delta | Rattus norvegicus (Norway rat) | Potency | 3.9811 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit gamma-2 | Rattus norvegicus (Norway rat) | Potency | 3.9811 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Glutamate receptor 2 | Rattus norvegicus (Norway rat) | Potency | 30.5756 | 0.0015 | 51.7393 | 15,848.9004 | AID1259244 |
| Gamma-aminobutyric acid receptor subunit alpha-5 | Rattus norvegicus (Norway rat) | Potency | 3.9811 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-3 | Rattus norvegicus (Norway rat) | Potency | 3.9811 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit gamma-1 | Rattus norvegicus (Norway rat) | Potency | 3.9811 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-2 | Rattus norvegicus (Norway rat) | Potency | 3.9811 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-4 | Rattus norvegicus (Norway rat) | Potency | 3.9811 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit gamma-3 | Rattus norvegicus (Norway rat) | Potency | 3.9811 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit alpha-6 | Rattus norvegicus (Norway rat) | Potency | 3.9811 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Nuclear receptor ROR-gamma | Homo sapiens (human) | Potency | 4.2163 | 0.0266 | 22.4482 | 66.8242 | AID651802 |
| Gamma-aminobutyric acid receptor subunit alpha-1 | Rattus norvegicus (Norway rat) | Potency | 3.9811 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit beta-3 | Rattus norvegicus (Norway rat) | Potency | 3.9811 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Gamma-aminobutyric acid receptor subunit beta-2 | Rattus norvegicus (Norway rat) | Potency | 3.9811 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| Peroxisome proliferator-activated receptor alpha | Homo sapiens (human) | Potency | 7.8435 | 0.0158 | 23.5273 | 44.6684 | AID651778 |
| GABA theta subunit | Rattus norvegicus (Norway rat) | Potency | 3.9811 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| ATPase family AAA domain-containing protein 5 | Homo sapiens (human) | Potency | 36.8823 | 0.0119 | 17.9420 | 71.5630 | AID651632; AID720516 |
| Ataxin-2 | Homo sapiens (human) | Potency | 30.5756 | 0.0119 | 12.2221 | 68.7989 | AID651632 |
| Gamma-aminobutyric acid receptor subunit epsilon | Rattus norvegicus (Norway rat) | Potency | 3.9811 | 1.0000 | 12.2248 | 31.6228 | AID885 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 5 (62.50) | 18.7374 |
| 1990's | 1 (12.50) | 18.2507 |
| 2000's | 1 (12.50) | 29.6817 |
| 2010's | 0 (0.00) | 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 weak demand-to-supply ratio for research on this compound.
| This Compound (11.88) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (11.11%) | 6.00% |
| Case Studies | 1 (11.11%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 7 (77.78%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||