Cetylpyridinium Chloride

HCID 31239

Basic information

CAS
123-03-5
Standard SMILES
CCCCCCCCCCCCCCCC[n+]1ccccc1.[Cl-]
InChIKey
YMKDRGPMQRFJGP-UHFFFAOYSA-M
Molecular formula
C21H38N.Cl
Average molar mass
340 g/mol

Overview

Cetylpyridinium chloride is a pyridinium salt that has N-hexadecylpyridinium as the cation and chloride as the anion. It has antiseptic properties and is used in solutions or lozenges for the treatment of minor infections of the mouth and throat. It has a role as a surfactant and an antiseptic drug. It is a chloride salt and an organic chloride salt. It contains a cetylpyridinium.

Names & identifiers

Preferred name
Cetylpyridinium Chloride
IUPAC
1-hexadecylpyridin-1-ium chloride
English name
Cetylpyridinium chloride
Molecular formula
C21H38ClN
Molecular weight
339.99

Names & synonyms

cetylpyridinium chloride123-03-5hexadecylpyridinium chloridePristacinPyriseptCepacolCeprimCetamiumDobendanAktivexBioseptAcetoquat CPC
Show more names
Cetylpyridinium Chloride (CPC)1-palmitylpyridiniumchlorideCetyl Pyridinium Chloride USP1-HEXADECYLPYRIDINIUM CHLORIDEceeprynmerocet
1-Cetylpyridinium chlorideCeepryn chlorideCepacol chlorideQuaternario CPCIntexsan CPCSwabettes HoechstAmmonyx CPCMedilave

Database identifiers

CAS
123-03-5、6004-24-6
PubChem CID
31239
DTXSID
DTXSID6041761
ChEMBL
CHEMBL2003538、CHEMBL34833
ChEBI
CHEBI:32915
UNII
6BR7T22E2S
EC Number
204-593-9

Properties

Computed structural properties

Topological polar surface area
3.9 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
15
Heavy atoms
23

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Quaternary Amines
CosmeticsEmulsifying; Deodorant; Hair conditioning; Antimicrobial; Antistatic; Surfactant
LogPlog Kow= 1.71
Color/FormWhite powder
SolubilityVery soluble in water, chloroform
DecompositionWhen heated to decomposition it emits very toxic fumes of /nitrogen oxides and hydrogen chloride/.

Physicochemical properties

Melting point
77 °C · 77°C
Boiling point
496.25 °C · 496.25°C (rough estimate)
Density
0.9362 · 0.9362 (rough estimate)
vapor pressure
0 Pa · 0Pa at 25℃
refractive index
1.6 · 1.6000 (estimate)
storage temp.
Inert atmosphere,Room Temperature

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 19.3% (36 of 187) of reports.

Danger

H301 (33.7%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P301+P317, P302+P352, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P330, P332+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 187 reports by companies from 27 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Hazard information

Regulatory Information · 6 items

Chemical: Pyridinium, 1-hexadecyl-, chloride (1:1)

Hazard Traits - Hazard Trait Undefined

Pyridinium, 1-hexadecyl-, chloride (1:1) is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pyridinium, 1-hexadecyl-, chloride (1:1) are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 25-01-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/17221

Pyridinium, 1-hexadecyl-, chloride: Does not have an individual approval but may be used under an appropriate group standard

1-Hexadecylpyridinium chloride: Does not have an individual approval but may be used under an appropriate group standard

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

Irritating to the skin and eyes; [HSDB] Allergic contact dermatitis is infrequently documented for quaternary ammonium compounds; [Marks, p. 266] Quaternary ammonium compounds have curare-like properties when concentrated solutions are ingested; Affected patients may have methemoglobinemia and hemolysis and die within 1-3 hours; Elevated liver function tests were reported; Concentrated solutions can cause burns; No data on carcinogenicity or teratogenicity; [IPCS-PIMs] See Benzalkonium chloride.

FIFRA Requirements · 1 item

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 chloride 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 chloride; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Hazard Classes and Categories · 3 items

Acute Tox. 3 (33.7%)

Acute toxicity (Oral) - Category 3

Acute toxicity (Oral) - Category 3

Skin, Eye, and Respiratory Irritations · 2 items

Mild skin irritation

A skin & eye irritant.

Safety & protection

Disposal Methods · 1 item

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.

Protective Action Criteria (PAC) · 3 items

0.060 [mg/m3]

0.66 [mg/m3]

4.0 [mg/m3]

Toxicology

Interactions · 4 items

AVOID ALCOHOL, WHICH HAS BEEN SHOWN TO INCREASE THE ORAL TOXICITY OF ... CETYL PYRIDINIUM CHLORIDE ... .

CURARE ANTAGONISTS SUCH AS NEOSTIGMINE AND EDROPHONIUM (TENSILON) ... MAY ENHANCE THE PARALYSIS ... . /BENZALKONIUM CHLORIDE/

... ANTAGONIZED BY ANIONIC SURFACTANTS, INCL SOAPS ... .

ETHANOL ACTIVATED UDP-GLUCURONOSYLTRANSFERASE ACTIVITY (P-NITROPHENOL SUBSTRATE) IN RAT LIVER IN VITRO, BUT INHIBITED ACTIVITY @ HIGHER ETHANOL CONCN. ACTIVATION NOT SEEN IN MICROSOMES PRETREATED IN VITRO WITH CETYLPYRIDINIUM CHLORIDE.

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 200(SRC), determined from a log Kow of 1.71(2) and a regression-derived equation(3), indicates that cetylpyridinium chloride 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)(4) and the mobility of cetylpyridinium bromide in soil may be considerably less than estimated. Volatilization of cetylpyridinium chloride from moist soil surfaces is not expected as this compound is a salt(SRC). Cetylpyridinium chloride is also not expected to volatilize from dry soil surfaces(SRC) as ions do not volatilize. Cetylpyridinium chloride is expected to biodegrade rapidly in soil(SRC) based on sewage studies for structurally-similar compounds. Dodecyl and tetradecylpyridinium chloride, were biodegraded in the Spanish official test (93 and 94%, respectively) and in the OECD Confirmatory test (91 and 92%, respectively)(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 200(SRC), determined from a log Kow of 1.71(2) and a regression-derived equation(3), indicates that cetylpyridinium chloride 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(5), an estimated BCF of 2(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Cetylpyridinium chloride is expected to biodegrade rapidly in water(SRC) based on sewage studies for structurally-similar compounds. Dodecyl and tetradecylpyridinium chloride, were biodegraded in the Spanish official test (93 and 94%, respectively) and in the OECD Confirmatory test (91 and 92%, respectively)(7).

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

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Soil Adsorption/Mobility · 1 item

The Koc of cetylpyridinium chloride is estimated as 200(SRC), using a measured log Kow of 1.71(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that cetylpyridinium chloride 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)(4) and the mobility of cetylpyridinium chloride in soil may be considerably less than estimated(SRC).

Human Toxicity Excerpts · 4 items

CONCN SOLN CAN PRODUCE CORROSIVE SKIN LESIONS WITH DEEP NECROSIS & SCARRING. /BENZALKONIUM CHLORIDE/

... POISONING FROM ORAL INGESTION HAS OCCURRED. /CATIONIC SURFACTANTS/

/Investigators/ ... studied the offspring of 292 women using this medication in the first trimester and found 9 malformations. The rate was 31 congenital defects per 1000 while the mean rate was 16 per 1000. This increase was not statistically significant.

Large quantities may cause nausea, vomiting, collapse, convulsions and coma.

Artificial Pollution Sources · 1 item

Cetylpyridinium chloride's production and use as an antiseptic, as a preservative in cosmetics and pharmaceuticals(1) and as an ingredient in external deodorants(2), and in mouthwash(3) may result in its release to the environment through various waste streams(SRC).

Regulatory information

FIFRA Requirements · 1 item

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 chloride 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 chloride; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Safety data

tsca
TSCA listed
ridadr
2811
hs_code
2933399990
Signal word
Danger
Symbol(GHS)
GHS06,GHS09
hazard_class
6.1(b)

Chemistry & industry

Pharmacology

Mechanism of Action · 3 items

MODE OF ACTION ... NOT YET FULLY UNDERSTOOD BUT HAS BEEN ASCRIBED TO ... THE DENATURING OF LIPOPROTEIN COMPLEXES, & POSSIBLY OTHER ACTIONS. /QUATERNARY AMMONIUM COMPD/

EVIDENCE HAS BEEN PRESENTED THAT THE MAJOR SITE OF ACTION ... MAY BE THE CELL MEMBRANE, WHERE THE AGENTS MAY CAUSE CHANGES IN PERMEABILITY THAT PERMIT ESCAPE OF ENZYMES, COENZYMES, & METABOLIC INTERMEDIATES. /CATIONIC SURFACTANTS/

EMULSIFY SEBACEOUS MATERIAL, WHICH IS THEN REMOVED TOGETHER WITH DIRT & BACTERIA. THE MILD DESQUAMATING EFFECT OF THE QUATERNARY AMMONIUM COMPOUNDS AIDS IN CLEANING. /QUATERNARY AMMONIUM COMPD/

MeSH Pharmacological Classification · 2 items

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.

Absorption, Distribution and ExcretionORAL RETENTION OF CETYLPYRIDINIUM CHLORIDE GIVEN AS 1 MIN MOUTH RINSE OF 10 ML OF 2.2 MMOL SOLN WAS 65% OF ADMIN DOSE.

Uses & manufacturing

Uses · 6 items

Used as a preservative/antibacterial agent in cosmetics, pharmaceuticals, cough lozenges, mouthwashes, deodorants, and antiseptics; [HSDB] Quarternary ammonium compounds are used as algaecides/slimicides (swimming pools, industrial water reservoirs, and farm ponds), antiseptics for cleaning wounds, antistatic agents for textiles, softeners for paper products, and pigment dispersers; [IPCS-PIMs]

Using Disinfectants or Biocides [Category: Clean]

For Cetylpyridinium chloride (USEPA/OPP Pesticide Code: 069160) 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."

Pharmaceutic aid (preservative), antiseptic; disinfectant/monohydrate/

Antiseptic; preservative(cosmetics, pharmaceuticals)

U.S. Imports(1974) 1.0X10+6 G (PRINCPL CUSTMS DISTS)
U.S. Production · 3 items

2023: 75,000 - <500,000 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 G

(1975) PROBABLY GREATER THAN 4.54X10+5 G

Consumption PatternsPROBABLY 100% AS AN ANTI-INFECTIVE/DISINFECTANT (1975)
Consumer UsesOther
Industry UsesPreservative
Applications · 3 items

DescriptionCetylpyridinium is a quaternary ammonium with broad-spectrum antiseptic activities. It is active against S. mutans, S. sanguis, E. coli, Oxford Staphylococcus, and C. albicans in media (MICs = 1.25-62.5 μg/ml) and against Oxford Staphylococcus in pooled human saliva (MICs = 7.8-15.6 μg/ml). Cetylpyridinium slows plaque formation for at least 21 days compared to a deionized water control in a rat incisor plaque model when applied topically at concentrations ranging from 0.025 to 2%. Formulations containing cetylpyridinium have been used as antiseptic agents in the treatment of gingivitis and as antimicrobial agents in raw food processing.

Usesquaternary ammonium compound used as a preservative in cosmetics and pharmaceuticals; topical anti-infective and disinfectant; used on the surface of latex gloves .

UsesAntibacterial in cough lozenges and syrups; emulsifier.

Upstream & downstream products

Suppliers101 total

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
兰州大圆新材料科技有限公司13992067598 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
Syntechem Co.,Ltd[email protected]

Additional notes

DefinitionChEBI: A pyridinium salt that has N-hexadecylpyridinium as the cation and chloride as the anion. It has antiseptic properties and is used in solutions or lozenges for the treatment of minor infections of the mouth and throat.

Related reactions

13 records

Compound notes

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