All Photos(4)

B1378

Sigma-Aldrich

2,6-Di-tert-butyl-4-methylphenol

≥99.0% (GC), powder

Synonym(s):
2,6-Di-tert-butyl-p-cresol, DBPC, Butylated hydroxytoluene, Butylhydroxytoluene, BHT
Linear Formula:
[(CH3)3C]2C6H2(CH3)OH
CAS Number:
Molecular Weight:
220.35
Beilstein:
1911640
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

vapor density

7.6 (vs air)

Quality Level

vapor pressure

<0.01 mmHg ( 20 °C)

assay

≥99.0% (GC)

form

powder

autoignition temp.

878 °F

bp

265 °C (lit.)

mp

69-73 °C (lit.)

solubility

ethanol: 100 mg/mL
vegetable oils: soluble

SMILES string

Cc1cc(c(O)c(c1)C(C)(C)C)C(C)(C)C

InChI

1S/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3

InChI key

NLZUEZXRPGMBCV-UHFFFAOYSA-N

Gene Information

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Related Categories

Packaging

1 kg in poly bottle
100, 500 g in poly bottle

Biochem/physiol Actions

Butylated hydroxytoluene (BHT) is a phenolic antioxidant. It has been shown to inhibit lipid peroxidation. It causes lung injury and promotes tumors in mice, but this may be due to a metabolite of BHT, 6-tert-butyl-2-[2′-(2′-hydroxymethyl)-propyl]-4-methylphenol. Metabolites of BHT have also been reported to induce DNA strand breaks and internucleosomal DNA fragmentation (a characteristic of apoptosis) in cultured cells. In rats, a single intraperitoneal injection of BHT (60 mg/kg body mass) results in a significant increase in nuclear DNA methyl transferase activity in the liver, kidneys, heart, spleen, brain and lungs. Incubation of alveolar macrophages with BHT significantly reduced the level of TNF-α which may explain the mechanism by which this antioxidant reduces inflammation. Preincubation of aspirin-treated platelets with BHT inhibits the secretion, aggregation, and protein phosphorylation induced by protein kinase C activators. BHT was also found to inhibit the initiation of hepatocarcinogenesis by aflatoxin B1.

pictograms

Environment

signalword

Warning

hcodes

Hazard Classifications

Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK Germany

WGK 2

Flash Point F

260.6 °F - open cup

Flash Point C

127 °C - open cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Nadja S Sieber-Ruckstuhl et al.
Scientific reports, 9(1), 6015-6015 (2019-04-14)
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Sara Wilhelmina Erasmus et al.
Foods (Basel, Switzerland), 9(8) (2020-08-17)
Alternative protein sources are gaining increasing global attention as a solution to address future protein demands. Determining the chemical composition of meat alternatives is vital to confirm that it is nutritious, but also to increase product value and promote its...
A M Vijesh et al.
European journal of medicinal chemistry, 46(11), 5591-5597 (2011-10-05)
In the present study two new series of Hantzsch 1,4-dihydropyridine derivatives (1,4-DHPs) containing substituted pyrazole moiety (4a-f and 5a-f) were synthesized by the reaction of 3-aryl-1H-pyrazole-4-carbaldehydes with 1,3-dicarbonylcompounds (ethylacetoacetate and methylacetoacetate) and ammonium acetate. The newly synthesized compounds were characterized...
Butylated hydroxytoluene (BHT): a review.
H Babich
Environmental research, 29(1), 1-29 (1982-10-01)
Stefanie Engleitner et al.
International journal of oncology, 56(4), 1034-1044 (2020-04-23)
Metastatic cancer cells cross endothelial barriers and travel through the blood or lymphatic fluid to pre‑metastatic niches, leading to their colonisation. 'S' stereoisomer 12S‑hydroxy‑5Z,8Z,10E,14Z‑eicosatetraenoic acid [12(S)‑HETE] is secreted by a variety of cancer cell types and has been indicated to...

Protocols

Analysis of Vitamin D in Milk and Infant Formula using UHPLC/MS/MS per AOAC Method 2011.11

While quantitative analysis was performed for Vitamins D2 and D3, the samples were scanned for the presence of the 25-hydroxy metabolites.

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