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B1378

Sigma-Aldrich

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

≥99.0% (GC), powder

Synonym(s):

2,6-Di-tert-butyl-p-cresol, BHT, Butylated hydroxytoluene, Butylhydroxytoluene, DBPC

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About This Item

Linear Formula:
[(CH3)3C]2C6H2(CH3)OH
CAS Number:
128-37-0
Molecular Weight:
220.35
Beilstein:
1911640
EC Number:
204-881-4
MDL number:
MFCD00011644
UNSPSC Code:
12352100
PubChem Substance ID:
57653920
NACRES:
NA.22
form:
powder
Assay:
≥99.0% (GC)
Pricing and availability is not currently available.

vapor density

7.6 (vs air)

Quality Level

200

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

human ... CAPN1(823)
rat ... Capn1(29153) , Nos1(24598)

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Application

  • Thermal decomposition characteristics of BHT and its peroxide (BHTOOH): BHT is highlighted for its excellent antioxidant properties, which degrade into BHTOOH under specific conditions (S Dai, et al., 2024).
  • Relaxation mechanisms in low-stress polymer networks: BHT is utilized in polymer networks to assess its effects on the mechanical properties and durability of dental composites (SH Lewis, et al., 2024).
  • Compatibility and safety of labels for pharmaceutical packaging: The study found BHT in labels, indicating its widespread use in pharmaceutical packaging due to its stabilizing properties (C Fu, et al., 2023).

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.

related product

Product No.
Description
Pricing

912395

NaBHT

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000374326
0000348560
0000348561
0000374325
BCCL3450

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Nadja S Sieber-Ruckstuhl et al.
Scientific reports, 9(1), 6015-6015 (2019-04-14)
Glucocorticoids (GCs) are critical regulators of metabolic control in mammals and their aberrant function has been linked to several pathologies. GCs are widely used in human and veterinary clinical practice as potent anti-inflammatory and immune suppressive agents. Dyslipidaemia is a
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
Gen-ichiro Arimura et al.
Plant physiology, 146(3), 965-973 (2008-01-01)
Continuous mechanical damage initiates the rhythmic emission of volatiles in lima bean (Phaseolus lunatus) leaves; the emission resembles that induced by herbivore damage. The effect of diurnal versus nocturnal damage on the initiation of plant defense responses was investigated using
Butylated hydroxytoluene (BHT): a review.
H Babich
Environmental research, 29(1), 1-29 (1982-10-01)
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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