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413135

Sigma-Aldrich

2,2′-Methylenebis(6-tert-butyl-4-methylphenol)

Synonym(s):

2,2′-Methylenebis(4-methyl-6-tert-butylphenol), 2,2′-Methylenebis(6-tert-butyl-p-cresol), 6,6-Methylenebis(2-tert-butyl-4-methylphenol)

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About This Item

Linear Formula:
CH2[C6H2[C(CH3)3](CH3)OH]2
CAS Number:
119-47-1
Molecular Weight:
340.50
EC Number:
204-327-1
MDL number:
MFCD00043641
UNSPSC Code:
12162002
PubChem Substance ID:
24865552
NACRES:
NA.23

form

powder

mp

123-127 °C (lit.)

SMILES string

Cc1cc(Cc2cc(C)cc(c2O)C(C)(C)C)c(O)c(c1)C(C)(C)C

InChI

1S/C23H32O2/c1-14-9-16(20(24)18(11-14)22(3,4)5)13-17-10-15(2)12-19(21(17)25)23(6,7)8/h9-12,24-25H,13H2,1-8H3

InChI key

KGRVJHAUYBGFFP-UHFFFAOYSA-N

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General description

2,2′-Methylenebis(6-tert-butyl-4-methylphenol) is a phenolic antioxidant commonly used in increasing the oxidation stability in rubber and plastic industries.

Application

It may be incorporated into the bromobutyl rubber(BIIR) matrix to enhance the overall thermo-reversibility of dicyclopentadiene dicarboxylic acid (DCPDCA) cross-linked BIIR. It may also be used as an antioxidant which shows a higher oxidation stability in distilled biodiesel.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360F

Hazard Classifications

Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Developmental toxicity of synthetic phenolic antioxidants to the early life stage of zebrafish.
Yang X, et al.
The Science of the Total Environment, 643, 559-568 (2018)
Rancimat and PetroOxy oxidation stability measurements of rapeseed oil methyl ester stabilized with hydrazides and antioxidants.
Bar F, et al.
Fuel: The Science and Technology of Fuel and Energy, 232(2), 108-113 (2018)
Y K Kim et al.
The Journal of antibiotics, 49(1), 31-36 (1996-01-01)
A new inhibitor of acyl-CoA:cholesterol acyltransferase (ACAT), designated GERI-BP002-A, was isolated from the culture broth of Aspergillus fumigatus F93 by acetone extraction, EtOAc extraction, SiO2 column chromatography and reverse phase HPLC. Spectroscopic analyses of the compound identified bis (2-hydroxy-3-tert-butyl-5-methylphenyl) methane
G R Brown et al.
Biochimica et biophysica acta, 1195(2), 252-258 (1994-11-02)
Bis-phenol, a phenolic antioxidant, is an inhibitor of sarcoplasmic reticulum (SR), endoplasmic reticulum (ER) and plasma membrane Ca2+ ATPases. The concentration of bis-phenol giving half-maximal inhibition of the SR Ca(2+)-ATPase is 2 microM. On binding to the SR Ca(2+)-ATPase it
Claire Harper et al.
Journal of cell science, 118(Pt 8), 1673-1685 (2005-04-07)
The sarcoplasmic-endoplasmic reticulum Ca(2+)-ATPase (SERCA) inhibitors thapsigargin (0.1-1 microM) and cyclopiazonic acid (10 microM), failed to affect resting [Ca(2+)] in human spermatozoa. Slow progesterone-induced [Ca(2+ i)](i) oscillations in human spermatozoa, which involve cyclic emptying-refilling of an intracellular Ca(2+) store were
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