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446424

Sigma-Aldrich

3,5-Di-tert-butyl-4-hydroxybenzyl alcohol

97%

Synonym(s):

3,5-Di-tert-butyl-4-hydroxyphenylmethanol, 4-Hydroxymethyl-2,6-di-tert-butylphenol

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About This Item

Linear Formula:
HOC6H2[C(CH3)3]2CH2OH
CAS Number:
88-26-6
Molecular Weight:
236.35
EC Number:
201-815-6
MDL number:
MFCD00017254
UNSPSC Code:
12352100
PubChem Substance ID:
24868276
NACRES:
NA.22

Assay

97%

form

solid

mp

139-141 °C (lit.)

functional group

hydroxyl

SMILES string

CC(C)(C)c1cc(CO)cc(c1O)C(C)(C)C

InChI

1S/C15H24O2/c1-14(2,3)11-7-10(9-16)8-12(13(11)17)15(4,5)6/h7-8,16-17H,9H2,1-6H3

InChI key

HNURKXXMYARGAY-UHFFFAOYSA-N

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Application

3,5-Di-tert-butyl-4-hydroxybenzyl alcohol can be used as a reactant to synthesize:      
  • 2,6-di-tert-butyl-4-(dodecylselanylmethyl)phenol and bis(3,5-di-tert-butyl-4-hydroxybenzyl) selenide by reacting with dodecaneselenolate and sodium selenide.      
  • Monomeric antioxidant by reacting with imidazole and N-[4-(chlorocarbonyl)phenyl]maleimide.     
  • Sulfur-containing butylated hydroxytoluene derivatives by reacting with aryl/alky dithiols.      
  • 3,5-Di-tert-butyl-4-hydroxybenzaldehyde by oxidation reaction using stabilized IBX.

Hazard Statements

H412

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 3

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW5702
MKCW9929
MKCW9771
MKCW9772
MKCW5632

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The antioxidant activity of 3, 5-di-tert-butyl-4-hydroxybenzyl derivatives.
Kim DH and Kummerow FA.
Journal of the American Chemical Society, 39(3), 150-155 (1962)
Synthesis of new polymeric antioxidants.
Oh DR, et al.
Bull. Korean Chem. Soc., 22(6), 629-632 (2001)
O L Brekke et al.
Cytokine, 4(4), 269-280 (1992-07-01)
The effect of commonly used food antioxidants on recombinant tumor necrosis factor alpha (rTNF-alpha)-induced cytotoxicity, growth enhancement and adhesion has been evaluated. Butylated hydroxyanisole (BHA) and 4-hydroxymethyl-2,6-di-t-butylphenol (HBP) were the only two of nine antioxidants that completely inhibited rTNF-alpha-induced cytotoxicity
X Guan et al.
Carcinogenesis, 16(10), 2575-2582 (1995-10-01)
The mouse pneumotoxicant and lung and liver tumor promoter butylated hydroxytoluene (BHT) was examined for its effects on gap junctional intercellular communication (GJIC) in mouse lung epithelial (C10) and rat liver epithelial (WB-F344) cell lines. GJIC, as measured by fluorescent
Melt-grafting of maleimides having hindered phenol group onto polypropylene.
Kim TH and Lee N.
Bull. Korean Chem. Soc., 24(12), 1809-1813 (2003)
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