1. Immunology/Inflammation
    NF-κB
    Metabolic Enzyme/Protease
    Apoptosis
  2. Reactive Oxygen Species
    Ferroptosis
  3. Butylhydroxyanisole

Butylhydroxyanisole (Synonyms: Butylated hydroxyanisole; BHA; E320)

Cat. No.: HY-B1066 Purity: >99.0%
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Butylhydroxyanisole (Butylated hydroxyanisole;BHA;E320) is an antioxidant used as a food additive preservative. Butylhydroxyanisole mediates liver toxicity, retardation in reproductive organ development and learning, and sleep deficit. Butylhydroxyanisole exerts neurotoxic effects and leads to disruption of the brain and nerve development.Butylhydroxyanisole also is a ferroptosis inducer.

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Butylhydroxyanisole Chemical Structure

Butylhydroxyanisole Chemical Structure

CAS No. : 25013-16-5

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Based on 2 publication(s) in Google Scholar

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Description

Butylhydroxyanisole (Butylated hydroxyanisole;BHA;E320) is an antioxidant used as a food additive preservative. Butylhydroxyanisole mediates liver toxicity, retardation in reproductive organ development and learning, and sleep deficit. Butylhydroxyanisole exerts neurotoxic effects and leads to disruption of the brain and nerve development[1][2][3].Butylhydroxyanisole also is a ferroptosis inducer[4].

In Vitro

Butylhydroxyanisole exerts neurotoxic effects by promoting cytosolic calcium accumulation and endoplasmic reticulum stress in astrocytes[1].
Butylhydroxyanisole (25-100 μM; 48 hours) inhibits growth and induces death in human astrocytes[1].
Butylhydroxyanisole (100 μM; 48 hours) decreases the expression of cell-cycle-related proteins and increased the expression of the cell cycle inhibitory protein[1].
Butylhydroxyanisole (100 μM; 48 hours) mediates apoptotic signals in NHA–SV40LT Cells[1].
Butylhydroxyanisole also increases the cytosolic calcium level and the expression of endoplasmic reticulum stress proteins[1].
Butylhydroxyanisole induces testicular dysfunction in mouse testis cells by dysregulating calcium homeostasis and stimulating endoplasmic reticulum stress[2].

Cell Proliferation Assay[1]

Cell Line: NHA–SV40LT cells
Concentration: 0 μM, 25 μM, 50 μM, 75 μM, 100 μM
Incubation Time: 48 hours
Result: Exerted ntiproliferative effects.

Cell Cycle Analysis[1]

Cell Line: NHA–SV40LT cells
Concentration: 100 μM
Incubation Time: 48 hours
Result: Downregulated the typical cell proliferative signaling pathways, phosphoinositide 3-kinase/protein kinase B and extracellular signal-regulated kinase 1/2.

Apoptosis Analysis[1]

Cell Line: NHA–SV40LT cells
Concentration: 100 μM
Incubation Time: 48 hours
Result: Increased the levels of pro-apoptotic proteins, such as BAX, cytochrome c, cleaved caspase 3, and cleaved caspase 9, and decreased the level of anti-apoptotic protein BCL-XL.

Western Blot Analysis[1]

Cell Line: NHA–SV40LT cells
Concentration: 100 μM
Incubation Time: 48 hours
Result: Increased the expression of pro-apoptotic proteins and decreased the levels of anti-apoptotic proteins. Asterisks show significant effects.
In Vivo

Butylhydroxyanisole (200 mg/kg; i.g.; daily; for three days) induces distinct expression patterns of Nrf2 and detoxification enzymes in the liver and small intestine of C57BL/6 mice[3].

Animal Model: Five-week-old C57BL/6 mice (WT and Nrf2-/-)[3]
Dosage: 200 mg/kg
Administration: Oral gavage, daily, for three days
Result: Increased Nqo1 staining in hepatocytes, predominately in the pericentral region.
Clinical Trial
Molecular Weight

180.24

Formula

C₁₁H₁₆O₂

CAS No.

25013-16-5

SMILES

OC1=CC=C(OC)C=C1C(C)(C)C.OC2=CC=C(OC)C(C(C)(C)C)=C2

Shipping

Room temperature in continental US; may vary elsewhere.

Storage
Powder -20°C 3 years
  4°C 2 years
In solvent -80°C 6 months
  -20°C 1 month
Solvent & Solubility
In Vitro: 

DMSO : ≥ 100 mg/mL (554.82 mM)

H2O : 1 mg/mL (5.55 mM; ultrasonic and warming and heat to 60°C)

*"≥" means soluble, but saturation unknown.

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 5.5482 mL 27.7408 mL 55.4816 mL
5 mM 1.1096 mL 5.5482 mL 11.0963 mL
10 mM 0.5548 mL 2.7741 mL 5.5482 mL
*Please refer to the solubility information to select the appropriate solvent.
References
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Keywords:

ButylhydroxyanisoleButylated hydroxyanisoleBHAE320E 320E-320Reactive Oxygen SpeciesFerroptosistoxicityneurotoxicantioxidantadditivepreservativetesticulardysfunctionstimulating endoplasmicreticulumstressendocrinedisruptorInhibitorinhibitorinhibit

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