Cetylpyridinium Bromide

HCID 8816CAS 140-72-7

基本情報

標準SMILES
CCCCCCCCCCCCCCCC[n+]1ccccc1.[Br-]
InChIKey
DVBJBNKEBPCGSY-UHFFFAOYSA-M
分子式
C21H38N.Br
平均分子量
384.4 g/mol

概要

Cetylpyridinium bromide is a pyridinium salt that has N-hexadecylpyridinium as the cation and bromide as the anion. It has a role as a surfactant, an antiseptic drug and an EC 2.7.11.18 (myosin-light-chain kinase) inhibitor. It is a bromide salt and a pyridinium salt.

名称と識別子

優先名称
Cetylpyridinium Bromide
IUPAC
1-hexadecylpyridin-1-ium bromide

名称と別名

140-72-7CETYLPYRIDINIUM BROMIDEHexadecylpyridinium bromide1-Hexadecylpyridinium bromideCetapharmNitrogenolSterogenalSterogenolBromocetCetasolCetazolCetazolin
名称をさらに表示
SeprisanHexadecylpyridine bromideN-Hexadecylpyridinium bromideAcetoquat CPBMorpan CBPTsPBCetyl pyridinium bromideHexadecylpyridiniumbromide

データベース識別子

CAS
140-72-7
PubChem CID
8816
DTXSID
DTXSID3033307
ChEMBL
CHEMBL334255
ChEBI
CHEBI:77052
UNII
O77BKZ14DE
EC Number
205-428-3

物性

構造計算による物性

極性表面積
3.9 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
15
重原子数
23

実験および物理化学的性質

Chemical ClassesNitrogen Compounds -> Quaternary Amines
LogPlog Kow= 1.83
Color/FormCream-colored, waxy solid
SolubilitySoluble in acetone, ethanol, and chloroform
DecompositionWhen heated to decomposition it emits toxic vapors of /nitrogen oxides/ and /bromides/.
Melting Point64.5 °C

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H302 (96.1%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P264+P265, P270, P271, P273, P280, P284, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 51 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 2 件

Chemical: Pyridinium, 1-hexadecyl-, bromide

Cetylpyridinium bromide: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Alkyl pyridinium surfactants
Hazards Summary · 1 件

Topical use during pregnancy unlikely to cause teratogenic effects; [ToxPlanet: TERIS] Causes changes in leukocyte count, dermatitis, and effects on true cholinesterase in 21-day intermittent dermal studies of rats; [RTECS] A severe irritant that may cause eye injury; Harmful by ingestion; Highly toxic by inhalation; Chloride salt: Not a skin sensitizer in guinea pigs; LC50 (rat) = 90 mg/m3/4hr; [Acros Organics MSDS] See Cetylpyridinium chloride.

FIFRA Requirements · 1 件

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Cetylpyridinium bromide is found on List C. Case No: 3013; Pesticide type: insecticide, fungicide, rodenticide, antimicrobial; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Cetylpyridinium bromide; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Hazard Classes and CategoriesAcute Tox. 4 (96.1%)

安全と保護具

Disposal Methods · 1 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

毒性情報

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 240(SRC), determined from a log Kow of 1.83(2) and a regression-derived equation(3), indicates that cetylpyridinium bromide is expected to have moderate mobility in soil(SRC). However, quaternary ammonium compounds are known to sorb strongly, and rapidly in well-mixed systems, to a wide variety of materials (such as sewage sludge, sediment, clay)(5) and the mobility of cetylpyridinium bromide in soil may be considerably less than estimated. Volatilization of cetylpyridinium bromide from moist soil surfaces is not expected as this compound is a salt(SRC). Cetylpyridinium bromide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.3X10-7 mm Hg(SRC), determined from a fragment constant method(4). Cetylpyridinium bromide is expected to biodegrade rapidly in the environment(SRC) based on studies using sewage(5,6); rates of biodegradation increased with acclimation of the microbial population(5,6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 240(SRC), determined from an measured log Kow of 1.83(2) and a regression-derived equation(3), indicates that cetylpyridinium bromide is not expected to adsorb to suspended solids and sediment(SRC). However, quaternary ammonium compounds are known to sorb strongly, and rapidly in well-mixed systems, to a wide variety of materials (such as sewage sludge, sediment, clay)(7); therefore, cetylpyridinium bromide should be strongly adsorbed to suspended solids and sediment in water. This compound is expected to exist in the dissociated form in the environment and therefore volatilization from water surfaces will not be an important fate process(SRC). According to a classification scheme(4), BCF values of 21, 22, and 13, measured for clams, fathead minnows, and tadpoles, respectively(5), suggest the potential for bioconcentration in aquatic organisms is low(SRC). Cetylpyridinium bromide is expected to biodegrade rapidly in the environment(SRC) based on studies using sewage(7,8); rates of biodegradation increased with acclimation of the microbial population(7,8).

ATMOSPHERIC FATE: Cetylpyridinium bromide will exist as the ion in the environment and, thus, will be present solely in the particulate phase in the atmosphere. Particulate-phase cetylpyridinium bromide may be removed from the air by wet and dry deposition.(SRC)

Soil Adsorption/Mobility · 1 件

Kd values for cetylpyridinium bromide on Sherman Island sediment and bentonite clay were 80 and 33,400, respectively(1). The Koc of cetylpyridinium bromide is estimated as 240(SRC), using a measured log Kow of 1.83(2) and a regression-derived equation(3). According to a classification scheme(4), this estimated Koc value suggests that cetylpyridinium bromide is expected to have moderate mobility in soil. However, quaternary ammonium compounds are known to sorb strongly, and rapidly in well-mixed systems, to a wide variety of materials (such as sewage sludge, sediment, clay)(5) and the mobility of cetylpyridinium bromide in soil may be considerably less than estimated(SRC).

Artificial Pollution SourcesCetylpyridinium bromide's production and use as a topical antiseptic/disinfectant(1) and as a deodorant, laboratory reagent, and surfactant(2) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 2 件

Biodegradation: at 18 mg/l (inoculum = sew.) lag period = 6 days; after 17 days complete degradation.

AEROBIC: Concentrations of up to 25 mg/l cetylpyridinium bromide were readily removed by model trickling filters acclimated to this compound; sorption was not a major process of removal as shown by extraction of slime layers(1). Cetylpyridinium bromide at 6 mg/l in the influent was not detected in effluent samples in model activated sludge systems(3). Cetylpyridinium bromide was completely degraded in 17 days in sewage(2). Another study shows 100% biodegradation in 3 days with this reduced to 2 days using the acclimated sewage in a second pass(2). Mean cetylpyridinium (counterion unspecified) removal of 96.0 and 77.2%, respectively, was observed at an activated sludge and a trickling filter wastewater treatment plant in England; in the Heidelsheim plant in Germany, 95% removal was reported(4).

Environmental Bioconcentration · 1 件

Whole body BCF values of 21, 22, and 13, were measured for clams, fathead minnows, and tadpoles, respectively, under flow-through conditions over a 7-day period(1). According to a classification scheme(2), these BCF values suggest the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 件

Cetylpyridinium bromide is expected to exist in the dissociated form in the environment and, therefore, volatilization from water surfaces or moist soil surfaces will not be an important fate process. Cetylpyridinium bromide is not expected to volatilize from dry soil surfaces as it exists as an ion in the environment and ions do not volatilize. (SRC)

法規制情報

FIFRA Requirements · 1 件

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Cetylpyridinium bromide is found on List C. Case No: 3013; Pesticide type: insecticide, fungicide, rodenticide, antimicrobial; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Cetylpyridinium bromide; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

化学と産業

薬理情報

MeSH Pharmacological Classification · 2 件

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects.

Purifying or cleansing agents, usually salts of long-chain aliphatic bases or acids, that exert cleansing (oil-dissolving) and antimicrobial effects through a surface action that depends on possessing both hydrophilic and hydrophobic properties.

用途と製造

Uses · 6 件

Used in mouthwashes, lozenges, and as a topical disinfectant; [TERIS] Used as a germicide, deodorant, laboratory reagent, surfactant, and topical antiseptic/disinfectant; [HSDB]

All active germicide/disinfectant/mildewcide pesticide product registrations cancelled in 1989 in the US; [NPIRS]

Using Disinfectants or Biocides [Category: Clean]

For Cetylpyridium bromide (USEPA/OPP Pesticide Code: 069118) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Germicide, deodorant, laboratory reagent, surfactant

Methods of ManufacturingPyridine + cetyl bromide (quaternization)
General Manufacturing InformationPyridinium, 1-hexadecyl-, bromide (1:1): ACTIVE

関連反応

3 件

関連ノート

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