Butylated hydroxytoluene

Butylated hydroxytoluene
Skeletal formula of butylated hydroxytoluene
Ball-and-stick model of the butylated hydroxytoluene molecule
Names
Preferred IUPAC name
2,6-Di-tert-butyl-4-methylphenol
Other names
  • 2,6-Di-tert-butyl-p-cresol
  • 2,6-DI-tert-butyl-4-methylphenol
  • 3,5-Di-tert-butyl-4-hydroxytoluene
  • DBPC
  • BHT
  • E321
  • AO-29
  • Avox BHT
  • Antioxidant 264
  • Additin RC 7110
  • Dibutylated hydroxytoluene
  • 4-Methyl-2,6-di-tert-butyl phenol
  • 3,5-(Dimethylethyl)-4-hydroxytoluene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.439 Edit this at Wikidata
EC Number
  • 204-881-4
E number E321 (antioxidants, ...)
KEGG
RTECS number
  • GO7875000
UNII
  • 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 checkY
    Key: NLZUEZXRPGMBCV-UHFFFAOYSA-N checkY
  • InChI=1/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3
    Key: NLZUEZXRPGMBCV-UHFFFAOYAU
  • CC(C)(C)c1cc(C)cc(c1O)C(C)(C)C
Properties
C15H24O
Molar mass 220.356 g/mol
Appearance White to yellow powder
Odor Slight, phenolic
Density 1.048 g/cm3
Melting point 70 °C (158 °F; 343 K)[4]
Boiling point 265 °C (509 °F; 538 K)[4]
1.1 mg/L (20 °C)[1]
log P 5.32[2]
Vapor pressure 0.01 mmHg (20 °C)[3]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable
GHS labelling:
GHS09: Environmental hazard
Warning
H410
P273, P391, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 127 °C (261 °F; 400 K)[4]
Lethal dose or concentration (LD, LC):
> 2,000 mg/kg (dermal, rat)[6]
NIOSH (US health exposure limits):
PEL (Permissible)
None[3]
REL (Recommended)
TWA 10 mg/m3[3]
IDLH (Immediate danger)
N.D.[3]
Safety data sheet (SDS) [5]
Related compounds
Related compounds
Butylated hydroxyanisole
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Butylated hydroxytoluene (BHT), also known as dibutylhydroxytoluene, is a lipophilic organic compound, chemically a derivative of phenol, that is useful for its antioxidant properties.[7] BHT is widely used to prevent free radical-mediated oxidation in fluids (e.g. fuels, oils) and other materials, and the regulations overseen by the U.S. F.D.A.—which considers BHT to be "generally recognized as safe"—allow small amounts to be added to foods. Despite this, and the earlier determination by the National Cancer Institute that BHT was noncarcinogenic in an animal model, societal concerns over its broad use have been expressed. BHT has also been postulated as an antiviral drug, but as of December 2022, use of BHT as a drug is not supported by the scientific literature and it has not been approved by any drug regulatory agency for use as an antiviral.[citation needed]

  1. ^ KEMI Anställd [KEMI Staff] (1994). "Teknisk beskrivning av ämnet—2,6-Bis(tert-butyl)-4-metylfenol 1994 [Information on substances—2,6-Bis(tert-butyl)-4-methylphenol 1994]" (in Swedish and English). Sundyberg, SE: KEMI [Swedish Chemicals Agency]. Archived from the original on 11 August 2011. Retrieved 14 March 2020. Vattenlöslighet: 1,1 mg/L (20 °C) [Water solubility: 1.1 mg/L (20 °C)][better source needed]
  2. ^ "2,6-di-tert-butyl-4-methylphenol". www.chemsrc.com.
  3. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0246". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ a b c "ICSC 0841 - BUTYLATED HYDROXYTOLUENE". www.inchem.org. March 1999.
  5. ^ "Safety data for 2,6-di-tert-butyl-p-cresol". ptcl.chem.ox.ac.uk. Archived from the original on 21 June 2002. Retrieved 17 January 2022.
  6. ^ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  7. ^ Yehye WA, Rahman NA, Ariffin A, Abd Hamid SB, Alhadi AA, Kadir FA, Yaeghoobi M (28 August 2015). "Understanding the Chemistry Behind the Antioxidant Activities of Butylated Hydroxytoluene (BHT): A Review". Eur. J. Med. Chem. 101: 295–312. doi:10.1016/j.ejmech.2015.06.026. PMID 26150290.

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