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112941

Sigma-Aldrich

tert-Butylhydroquinone

97%

Synonym(s):

2-(1,1-Dimethylethyl)-1,4-benzenediol, NSC 4972

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About This Item

Linear Formula:
(CH3)3CC6H3-1,4-(OH)2
CAS Number:
1948-33-0
Molecular Weight:
166.22
Beilstein/REAXYS Number:
637923
EC Number:
217-752-2
MDL number:
MFCD00002344
UNSPSC Code:
12162002
PubChem Substance ID:
24847122
NACRES:
NA.23

Quality Level

200

assay

97%

autoignition temp.

855 °F

mp

127-129 °C (lit.)

SMILES string

CC(C)(C)c1cc(O)ccc1O

InChI

1S/C10H14O2/c1-10(2,3)8-6-7(11)4-5-9(8)12/h4-6,11-12H,1-3H3

InChI key

BGNXCDMCOKJUMV-UHFFFAOYSA-N

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General description

tert-Butylhydroquinone (TBHQ) is a phenolic antioxidant. TBHQ is frequently used as a food preservative. In low concentrations it shows cytoprotective qualities while at higher concentrations it exhibits cytotoxic behavior.

Application

TBHQ was used to study the inactivation of barotolerant strains of Listeria monocytogenes and Escherichia coli. Environment friendly electrode materials for supercapacitors were attained by decorating the surface of graphene nanosheets with TBHQ.

pictograms

Exclamation markEnvironment
GHS07,GHS09

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Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

195.8 °F - closed cup

flash_point_c

91 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX2346
MKCX2345
MKCV5562
MKCV4260
MKCV0508

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Tatsuya Ogawa et al.
Clinical, cosmetic and investigational dermatology, 13, 657-660 (2020-09-29)
The stratum corneum protects against the entry of pathogens, allergens, and irritants while preventing dehydration. The Kelch-like erythroid cell-derived protein with cap-n-collar homology-associated protein 1 (KEAP1)/NF-E2-related factor 2 (NRF2) system maintains skin barrier homeostasis. Aggregated evidence suggests that NRF2-mediated antioxidative
Tert-butylhydroquinone-decorated graphene nanosheets and their enhanced capacitive behaviors
Wang HW, et al.
Chinese Science Bulletin, 56(20), 2092-9097 (2011)
Yoon-Kyung Chung et al.
Journal of microbiology (Seoul, Korea), 46(3), 289-294 (2008-07-08)
Antimicrobial efficacy of ultra-high-pressure (UHP) can be enhanced by application of additional hurdles. The objective of this study was to systematically assess the enhancement in pressure lethality by TBHQ treatment, against barotolerant strains of Escherichia coli O157:H7 and Listeria monocytogenes.
Saelooom Lee et al.
Free radical biology & medicine, 53(4), 807-816 (2012-06-12)
Radiotherapy and chemotherapeutic agents can effectively induce apoptosis through generation of reactive oxygen species (ROS). Cancer cells frequently express high levels of ROS-scavenging enzymes, which confer resistance to ROS-mediated cell death. Keap1 (Kelch-like ECH-associated protein 1) sequesters and promotes the
Michael J Steinbaugh et al.
American journal of physiology. Endocrinology and metabolism, 303(4), E488-E495 (2012-06-14)
Xenobiotic metabolism has been proposed to play a role in modulating the rate of aging. Xenobiotic metabolizing enzymes (XME) are expressed at higher levels in calorically restricted mice (CR) and in GH/IGF-I-deficient, long-lived mutant mice. In this study, we show
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