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94-26-8

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Identification

Name
Butylparaben
CAS
94-26-8
Synonyms
4-(butoxycarbonyl)phenol
4-HYDROXYBENZOIC ACID BUTYL ESTER
4-HYDROXYBENZOIC ACID N-BUTYL ESTER
butoben
BUTYL 4-HYDROXYBENZOATE
BUTYL CHEMOSEPT
BUTYLPARABEN
butyl parabens
BUTYL PARASEPT
BUTYL P-HYDROXYBENZOATE
FEMA 2203
N-BUTYL 4-HYDROXYBENZOATE
N-BUTYLPARABEN
N-BUTYL P-HYDROXYBENZOATE
P-HYDROXYBENZOIC ACID BUTYL ESTER
P-HYDROXYBENZOIC ACID N-BUTYL ESTER
4-hydroxy-benzoicacibutylester
4-Hydroxybenzoicaicdbutylester
Aseptoform Butyl
aseptoformbutyl
EINECS(EC#)
202-318-7
Molecular Formula
C11H14O3
MDL Number
MFCD00016478
Molecular Weight
194.23
MOL File
94-26-8.mol

Chemical Properties

Appearance
white crystalline powder
Melting point 
67-70 °C(lit.)

mp 
67-70 °C(lit.)

Boiling point 
156-157 °C3.5 mm Hg(lit.)

bp 
156-157 °C3.5 mm Hg(lit.)

density 
1.28
refractive index 
1.5115 (estimate)
FEMA 
2203
Fp 
181℃
storage temp. 
0-6°C
solubility 
Soluble in DMSO, ethyl acetate, methanol.
form 
Crystalline Powder
pka
pKa 8.5 (Uncertain)
color 
White to almost white
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents, strong alkalies.
Water Solubility 
<0.1 g/100 mL at 17 ºC
Merck 
14,1584
JECFA Number
870
BRN 
1103741
Contact allergens
This substance is one of the parabens family. Parabens are esters formed by p-hydroxybenzoic acid and an alcohol. They are largely used as biocides in cosmetics and toiletries, medicaments, or food. They have synergistic power with other biocides. Parabens can induce allergic contact dermatitis, mainly in chronic dermatitis and wounded skin.
InChIKey
QFOHBWFCKVYLES-UHFFFAOYSA-N
CAS DataBase Reference
94-26-8(CAS DataBase Reference)
NIST Chemistry Reference
P-hydroxybenzoic acid, n-butyl ester(94-26-8)
EPA Substance Registry System
94-26-8(EPA Substance)

Safety Data

Risk Statements 
R36/37/38:Irritating to eyes, respiratory system and skin .
Safety Statements 
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
WGK Germany 
2

RTECS 
DH1980000

TSCA 
Yes
HS Code 
29182900
Hazardous Substances Data
94-26-8(Hazardous Substances Data)

Raw materials And Preparation Products

Hazard Information

General Description
Odorless white crystals or crystalline powder. Tasteless, but numbs the tongue. Aqueous solutions slightly acidic to litmus.
Reactivity Profile
N-BUTYL-P-HYDROXYBENZOATE(94-26-8) is incompatible with strong oxidizing agents and strong caustics.
Air & Water Reactions
Insoluble in water.
Fire Hazard
Flash point data for this chemical are not available; however, N-BUTYL-P-HYDROXYBENZOATE is probably combustible.
Description
In vivo anti-trypanosomal activity of imidazo[1,2-a]pyridiness in the STIB900 mouse model has been investigated.
Preparation
Butyl paraben is prepared by esterifying p-hydroxybenzoic acid with butyl alcohol in the presence of an acid catalyst, such as sulfuric acid, and an excess of the specific alcohol.
Production Methods
Butylparaben is prepared by esterification of p-hydroxybenzoic acid with n-butanol.
Pharmaceutical Applications
Butylparaben is widely used as an antimicrobial preservative in cosmetics and pharmaceutical formulations.
It may be used either alone or in combination with other paraben esters or with other antimicrobial agents. In cosmetics, it is the fourth most frequently used preservative.
As a group, the parabens are effective over a wide pH range and have a broad spectrum of antimicrobial activity, although they are most effective against yeasts and molds.
Owing to the poor solubility of the parabens, paraben salts, particularly the sodium salt, are frequently used in formulations. However, this may raise the pH of poorly buffered formulations. See Methylparaben for further information.
Safety
Butylparaben and other parabens are widely used as antimicrobial preservatives in cosmetics and oral and topical pharmaceutical formulations.
Systemically, no adverse reactions to parabens have been reported, although they have been associated with hypersensitivity reactions generally appearing as contact dematitis. Immediate reactions with urticaria and bronchospasm have occurred rarely. See Methylparaben for further information.
LD50 (mouse, IP): 0.23 g/kg
LD50 (mouse, oral): 13.2 g/kg
storage
Aqueous butylparaben solutions at pH 3–6 can be sterilized by autoclaving, without decomposition. At pH 3–6, aqueous solutions are stable (less than 10% decomposition) for up to about 4 years at room temperature, while solutions at pH 8 or above are subject to rapid hydrolysis (10% or more after about 60 days at room temperature).
Incompatibilities
The antimicrobial activity of butylparaben is considerably reduced in the presence of nonionic surfactants as a result of micellization. Absorption of butylparaben by plastics has not been reported but appears probable given the behavior of other parabens. Some pigments, e.g. ultramarine blue and yellow iron oxide, absorb butylparaben and thus reduce its preservative properties.
Butylparaben is discolored in the presence of iron and is subject to hydrolysis by weak alkalis and strong acids.
Regulatory Status
Included in the FDA Inactive Ingredients Database (injections; oral capsules, solutions, suspensions, syrups and tablets; rectal, and topical preparations). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Nonmedicinal Ingredients.

Material Safety Data Sheet(MSDS)

Questions And Answer

Chemical properties
It appears as white crystal powder, having slightly special odor. It is slightly soluble in water, being soluble in alcohol, ether and chloroform.
Production method
It is derived from the esterification between p-hydroxybenzoic acid and butanol. Butanol and p-hydroxybenzoic acid are heated together for being dissolved, slowly added dropwise of sulfuric acid, continue the refluxing for 8h. After cooling, add 4% sodium carbonate solution, separate the water layer, steam out the butanol, let it cool, filter to obtain the crude product, and then carry out ethanol recrystallization (solubility in ethanol: 200g/100ml).
Take sulfuric acid as a catalyst; derive it from the reaction between p-hydroxybenzoic acid and butanol.
Uses
1. Butylparaben can be used for the antibacterial and anticorrosion of drugs, cosmetics and food.
2. As a kind of preservative; Because of the low solubility in water, Butylparaben is usually prepared into ethanol solution, acetic acid solution or sodium hydroxide solution. To improve the solubility, several different esters are often used. For example, three parts of isobutyl, four parts of isopropyl and three parts of butyl are formulated as a co-soluble mixture and the mixture is used as an oil-in-water emulsifier. This preparation is easy to use in soy sauce and other foods, the solubility of butyl ester alone can be increased by 2 to 3 times. For soy sauce, 5% sodium hydroxide solution can be added to the goods of 20% to 25%, and then slowly added to the sauce having been heated to about 80 ℃. Acetic acid solution or ester type emulsifier can also be used. The usage amount of anti-mold soy sauce is 0.05~0.10g/L. Vinegar can be used in acetic acid or sodium hydroxide solution. Soft drinks can be used in the solution of sodium hydroxide, but usually used in combination with benzoic acid and dehydroacetic acid.
3. Used as organic synthesis intermediates; the anti-corrosion additives of medicine, food, cosmetics, film and high-grade products; reagents. Being used as germicide preservative of food is Butylparaben's major application. In the p-hydroxybenzoic acid esters, it can give the strongest anti-corrosion bactericidal effect. Because of its poor water solubility, it is often used with other esters in combination.
4. For preservatives and disinfectants
Toxicity
ADI is subject to postponed decision (FAO/WHO, 2001).
LD50: 16.0 g/kg (mouse, subcutaneous injection).
Mice subjecting to short-term toxicity test have gotten inhibited weight increase. There have been reports regarding to the acute dermatitis for human beings. In the p-hydroxybenzoic acid esters, this product gives the best anti-corrosion effect, but also the largest toxicity.
Content analysis
2g (accurate to 0.1mg) was taken and dried in silica gel for 5h before being transferred to the flask. Add 40 mL of 1mol/L of sodium hydroxide, flush flasks with water. Cover the surface of the dish and apply a small fire to boil 1h before cooling. Add 5 drops of bromothymol blue solution (TS-56), titrate the excess sodium hydroxide with 1 mol/L sulfuric acid, and make the color of the solution consistent with the buffer containing the same indicator (pH 6.5). Carry out a blank test at the same time and make the necessary calibration. 1ml/L sodium hydroxide per milliliter corresponds to the 194.2 mg of this product (C11H14O3).
Usage limit
Japan (1998, calculated on p-hydroxybenzoic acid; the data in parentheses is the amount converted into equivalent amount of this product, g/ kg), soy sauce 0.25 g/L (0.35 g/L), vinegar 0.1 g/L (0.14 g/L); Soft drinks and syrup: 0.1 (0.14); fruit sauce: 0.2 (0.28); fruits and vegetables 0.012 (0.016).
Hazards & Safety Information
Category :Toxic substances
Toxic classification: poisoning
Acute toxicity:  Oral-mouse LD50: 13200 mg/kg; celiac-mouse LD50: 230 mg/kg
Stimulation Data:  Skin-Guinea Pig 5%/48 hours Mild
Flammability and Hazardous characteristics:  Thermal decomposition; pungent irritation Smoke
Storage and transportation characteristics:  Treasury: ventilated, low temperature and dry
Fire extinguishing agent:  water, dry powder, foam, carbon dioxide

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