Dodecyldimethylaminoxid

Cosmetic ingredients (Lauramine Oxide) -> CIR (Cosmetic Ingredient Review)

Hair conditioning; Antistatic; Cleansing; Surfactant; Viscosity controlling; Foam boosting; Hydrotrope

266 to 268 °F (NTP, 1992)

130.5 °C

Dimethyldodecylamine-n-oxide is a crystalline solid.

Liquid; CBI

Highly hygroscopic solid; [HSDB]

This chemical does not meet GHS hazard criteria for 3.1% (35 of 1145) of reports.

Danger

H302 (30.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P354+P338, P317, P321, P330, P332+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1145 reports by companies from 32 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Chemical: 1-Dodecanamine, N,N-dimethyl-, N-oxide

Regulation (EC) No 1935/2004 (amended)

1-Dodecanamine, N,N-dimethyl-, N-oxide is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Dodecanamine, N,N-dimethyl-, N-oxide 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)

REACH registered substance: Dodecyldimethylamine oxide (EC: 216-700-6)

Dodecyldimethylamine oxide: Does not have an individual approval but may be used under an appropriate group standard

Caused severe skin irritation (including severe erythema and edema, fissuring with bleeding, and necrosis) in rabbit studies; High dose animal feeding studies produced no significant adverse effects; [HSDB] Amine oxides are metabolized and rapidly excreted after ingestion; Effects on skin are: 1% solutions not irritating, 5% solutions moderately irritating, and 30% solutions severely irritating; No evidence of skin sensitization; No evidence of carcinogenic response or reproductive toxicity; [OECD SIDS] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis; [MSDSonline]

DIMETHYLDODECYLAMINE-N-OXIDE is less basic than the tertiary amine from which it is derived, but still reacts with strong acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Acute Tox. 4 (30.8%)

Acute toxicity (Oral) - Category 4

Skin corrosion/irritation - Category 2

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5.5(SRC), determined from a water solubility of 190,000 mg/L(2) and a regression-derived equation(3), indicates that lauramine oxide is expected to have very high mobility in soil(SRC). Volatilization of lauramine oxide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.6X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Lauramine oxide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.2X10-8 mm Hg(SRC), determined from a fragment constant method(5). In aqueous biodegradation screening tests, lauramine oxide was 100% removed after 28 days as measured by liquid chromatography-mass spectrometry(6), suggesting that biodegradation in soil is an important fate process(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5.5(SRC), determined from a water solubility of 190,000 mg/L(2) and a regression-derived equation(3), indicates that lauramine oxide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 6.6X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 0.7(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). In aqueous biodegradation screening tests, lauramine oxide was 100% removed after 28 days as measured by liquid chromatography-mass spectrometry(6), suggesting that biodegradation in water is an important fate process(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), lauramine oxide, which has an estimated vapor pressure of 6.2X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase lauramine oxide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 14.1 hours(SRC), calculated from its rate constant of 2.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3) Particulate-phase lauramine oxide may be removed from the air by wet or dry deposition(SRC). Lauramine oxide does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

On the basis of the available animal and clinical data presented in this report, the CIR Expert Panel concludes that Lauramine Oxide and Stearamine Oxide are safe as cosmetic ingredients for "rinse-off" products under present conditions of use. For use in "leave-on" products, the Expert Panel concludes that Lauramine Oxide should be limited to 3.7% and Stearamine Oxide to 5%.

Safe for use in cosmetics, with qualifications

The Koc of lauramine oxide is estimated as 5.5(SRC), using a water solubility of 190,000 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that lauramine oxide is expected to have very high mobility in soil.

AEROBIC: Lauramine oxide, present at 100 mg/L, was 100% removed in 4 weeks as measured by liquid chromatography-mass spectrometry, using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(1). An inherent biodegradability test using an activated sludge inoculum at 100 mg/L and lauramine oxide at 30 mg/L showed the compound to reach 88% of its theoretical total organic carbon in 4 weeks(1).

An estimated BCF of 0.7 was calculated for lauramine oxide(SRC), using a water solubility of 190,000 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Henry's Law constant for lauramine oxide is estimated as 6.6X10-11 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that lauramine oxide is expected to be essentially nonvolatile from water surfaces(2). Lauramine oxide's Henry's Law constant indicates that volatilization from moist soil surfaces is not likely to occur(SRC). Lauramine oxide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.2X10-8 mm Hg(SRC), determined from a fragment constant method(3).

/LABORATORY ANIMALS: Acute Exposure/ The ocular irritation potential of formulations containing 0.3% active lauramine oxide was evaluated by instilling 10 uL into the conjunctival sac of New Zealand White rabbits. The eyes of some rabbits were rinsed with distilled water. Irritation was scored according to the method of Draize (maximum possible score: 110). Slight irritation of the conjunctivae was observed in all unrinsed eyes and in two of three rinsed eyes at the 24-hr grading period. The maximum average score was 2.0 for the animals with unrinsed eyes, and 1.3 for those whose eyes were rinsed. All eyes were clear after 48 hr.

/LABORATORY ANIMALS: Acute Exposure/ The primary dermal irritation potential of three formulations, each containing 30% lauramine oxide, was evaluated using New Zealand white rabbits. Three male and three female rabbits had 0.5 mL of each formulation applied under occlusive patches to separate sites on their clipped backs for 24 hr. The sites were rinsed after patch removal and were scored for erythema, eschar, and edema at the time of removal and 48 hr later. The primary dermal indices (maximum possible score: 8) were 7.0, 7.2, and 7.6. Moderate to severe erythema and edema, two cases of necrosis, and one case of necrosis and fissuring with bleeding were observed at the 24-hr grading period. At the 72-hr reading, ... severe erythema and edema, eschar, fissuring with bleeding, and necrosis and/or thickened skin /did occur/.

/LABORATORY ANIMALS: Acute Exposure/ Liquid droplet aerosol /formulation containing 0.3% active lauramine oxide/ at concentrations of 0.2, 1.0, and 5.2 mg/L were tested on three groups of four male Swiss-Webster mice. Only the heads of the mice were exposed to the aerosol. The average respiratory rate was monitored using plethysmography 5 min before, 10 min during, and 10 min after each exposure, and the percentage change in respiratory rate was calculated. A decrease in respiratory rate was considered a response to upper airway irritation. A transient decrease was observed in the respiratory rate of the 1.0 mg/L exposed group, but this was not considered significant because no signs of irritation were seen at greater exposure concentrations. The groups treated with 1.0 mg/L and 5.2 mg/L had a 6% decrease in their average respiratory rates. However, these decreases were not attributed to upper airway irritation because the respiratory rates were even lower during the postexposure recovery period. No decrease in respiratory rate was observed in the 0.2 mg/L exposed mice.

/LABORATORY ANIMALS: Acute Exposure/ The acute inhalation toxicity of a liquid droplet aerosol formulation containing 0.3% active lauramine oxide was evaluated. Five female and five male albino Sprague-Dawley-derived rats were exposed for 4 hr to this aerosol at a concentration of 5.3 mg/L. The Equivalent Aerodynamic Diameter of the aerosol was 3.6 um with a geometric standard deviation of 1.91. The animals were observed during the exposure and two times daily for 14 days, and body weights were recorded before exposure and on days 1, 3, 7, and 14 postexposure. At necropsy, the major organs in the abdominal and thoracic cavities were weighed and observed. No deaths occurred during the study and all the rats appeared normal. A slight drop in body weight was observed in the males on day 1, but weight was gained normally for the remainder of the study. The weight gain in the females was normal. The organ weights were all within the anticipated normal control ranges for both sexes. No exposure-related pharmacotoxic signs were evident in any of the organs. The 4-hr LD50 for this aerosol was greater than 5.3 mg/L nominal.

For more Non-Human Toxicity Excerpts (Complete) data for LAURAMINE OXIDE (12 total), please visit the HSDB record page.

The rate constant for the vapor-phase reaction of lauramine oxide with photochemically-produced hydroxyl radicals has been estimated as 2.7X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 14.1 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Lauramine oxide is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Lauramine oxide does not contain chromophores that absorb at wavelengths >290 nm(2) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 91,001 workers (38,251 of these were female) were potentially exposed to lauramine oxide in the US(1). Occupational exposure may occur through dermal contact with this compound at workplaces where lauramine oxide is produced or used. The general population may be exposed to lauramine oxide via dermal contact with this compound and consumer products containing lauramine oxide(SRC).

Lauramine oxide's production and use as a surfactant in dishwasher detergent, shampoo and soap, as a foam stabilizer, and textile antistatic agent may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 6.2X10-8 mm Hg at 25 °C indicates lauramine oxide will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase lauramine oxide will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 14.1 hours. Particulate-phase lauramine oxide will be removed from the atmosphere by wet or dry deposition. Lauramine oxide does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight. If released to soil, lauramine oxide is expected to have very high mobility based upon an estimated Koc of 5.5. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 6.6X10-11 atm-cu m/mole. In aqueous biodegradation screening tests, lauramine oxide was 100% removed after 28 days as measured by liquid chromatography-mass spectrometry, suggesting that biodegradation in soil and water is an important fate process. If released into water, lauramine oxide is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 0.7 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to lauramine oxide may occur through dermal contact with this compound at workplaces where it is produced or used. The general population may be exposed to lauramine oxide via dermal contact with this compound in consumer products containing lauramine oxide. (SRC)

Metabolic profiles for different species (rat, human, mouse, rabbit) did not have any significant differences in metabolites, but the degree of absorption, especially in cutaneous applications, varied from species to species.

Characterization of metabolites of lauramine oxide resulted in the positive identification of only one metabolite, N-dimethyl-4-aminobutyric acid N-oxide. Several pathways exist for metabolism of lauramine oxide: omega,beta-oxidation of alkyl chains (the most common pathway for surfactant metabolism), hydroxylation of alkyl chains, and reduction of the amine oxide group.

Urinary metabolites in rats, rabbits and humans suggested metabolism via omega, beta-oxidation of the aliphatic chain, amine oxide reduction and aliphatic, mid-chain hydroxylation. N,N-dimethyl-4-aminobutyric acid and its N-oxide accounted for 28, 28 and 23% in man, rats and rabbits, respectively.

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.

Agents that modify interfacial tension of water; usually substances that have one lipophilic and one hydrophilic group in the molecule; includes soaps, detergents, emulsifiers, dispersing and wetting agents, and several groups of antiseptics.

(1-Dodecyl-14C)lauramine oxide (10 mg with 100 uCi of 14C) was applied to the skin of two humans to study cutaneous absorption and metabolism of lauramine oxide. Ninety-two percent of the applied radioactivity was recovered from the skin of the test subjects 8 hr after dosing, and 0.1 and 0.23% of the radioactivity was recovered from the excretion products of the test subjects. The stratum corneum contained <0.2% of the applied dose.

Oral administration of a solution containing 50 mg (1-dodecyl-14C)lauramine oxide (100 uCi of 14C) to two humans resulted in excretion patterns of radioactivity similar to that of the other species studied. Fifty percent and 37% of the radioactivity was found in the urine within 24 hr of dosing, and expired 14C02 contained between 18 and 22% of the radioactivity administered.

Four Sprague-Dawley rats were given intraperitoneal injections of 22 mg (methyl-14C)lauramine oxide kg (specific activity 1.3 mCi/g). Sixty-seven percent of the total radioactivity was eliminated in the urine, 8% was expired as I4CO2, and 6% was eliminated in the feces within 24 hr. The distribution of radioactivity was essentially the same as that seen in rats given oral doses of lauramine oxide. The conclusion was that "... microbial metabolism by gastrointestinal flora does not play a major role in the absorption and excretion of [lauramine oxide] in rats."

Aqueous (methyl-14C)lauramine oxide (10 mg containing 1.3 mCi/g) was applied to the skin of four Sprague-Dawley rats to test metabolism and absorption of the compound. Over 72 hr, 14.2% of the total radioactivity was found in the urine, 2.5% in the CO2, and 1.8% in the feces. Radioactivity was detected in the liver, kidneys, testes, blood, and expired CO2.

For more Absorption, Distribution and Excretion (Complete) data for LAURAMINE OXIDE (7 total), please visit the HSDB record page.

CIR ingredient: Lauramine Oxide

Used as a foam builder and stabilizer; Used in cosmetics, emollients, conditioners, emulsifiers, dishwasher detergents, shampoos, soaps, and antistatic, wetting, antibacterial, and antifungal agents; [HSDB]

Using Disinfectants or Biocides [Category: Clean]

As a foam stabilizer; stable at high concentration of electrolytes and over a wide pH range.

Lauramine oxide and stearamine oxide are aliphatic tertiary amine oxides that are used in cosmetics as foam builders and stabilizers, viscosity enhancers, emollients, conditioners, emulsifiers, antistatic agents, and wetting agents.

Surfactant amine oxides such as lauryldimethylamine oxide are ... widely used as constituents of dishwasher detergents, shampoos, and soaps.

(1979) No Data

(1981) No Data

(1979) No Data

(1981) No Data

2023: 10,000,000 - <25,000,000 lb

(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS

(1981) 2.7X10+10 G (ESTIMATED)

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5403]

1-Dodecanamine, N,N-dimethyl-, N-oxide is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

EPA Safer Chemical Functional Use Classes -> Surfactants

Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern

Fragrance Ingredients

Cosmetics -> Hair conditioning; Antistatic; Cleansing; Surfactant; Viscosity controlling; Foam boosting; Hydrotrope

Paint and Coating Manufacturing

1-Dodecanamine, N,N-dimethyl-, N-oxide: ACTIVE

"AROMOX" /IS/ TRADEMARK FOR A SERIES OF METHYLATED OR ETHOXYLATED AMINE OXIDES DERIVED FROM HIGH-MOLECULAR-WT ALIPHATIC AMINES. USES: FOAM & SUDS STABILIZERS IN DETERGENT & COSMETIC FORMULATIONS; SURFACTANTS. /AROMOX/