Propanoic acid, 3,3'-thiobis-, didodecyl ester

Other Classes -> Esters, Other

Antioxidant

Cosmetic ingredients (Dilauryl Thiodipropionate) -> CIR (Cosmetic Ingredient Review)

Antioxidant

40 °C

43 - 44 °C

0.00000001 [mmHg]

Vapor pressure = 0.2 mm Hg at 163 deg

This chemical does not meet GHS hazard criteria for 65.8% (340 of 517) of all reports.

H412 (30.8%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P273, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 517 reports by companies from 8 notifications to the ECHA C&L Inventory.

Chemical: Propanoic acid, 3,3'-thiobis-, didodecyl ester

Propanoic acid, 3,3'-thiobis-, 1,1'-didodecyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propanoic acid, 3,3'-thiobis-, 1,1'-didodecyl ester 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: 06-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13602

Dilauryl thiodipropionate: Does not have an individual approval but may be used under an appropriate group standard

Specific prior-sanctioned food ingredients. Substances classified as antioxidants, when migrating from food-packaging material (limit of addition to food, 0.005%) shall include: ... dilauryl thiodipropionate.

This substance is generally recognized as safe for use in food when the total content of antioxidants is not over 0.02 percent of fat or oil content, including essential (volatile) oil content of the food, provided the substance is used in accordance with good manufacturing practice.

This substance is generally recognized as safe for use in food when the total content of antioxidants is not over 0.02 percent of fat or oil content, including essential (volatile) oil content of the food, provided the substance is used in accordance with good manufacturing or feeding practice.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 9X10+6(SRC), determined from a structure estimation method(2), indicates that dilauryl thiodipropionate is expected to be immobile in soil(SRC). Volatilization of dilauryl thiodipropionate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(2), and dilauryl thiopropionate's strong adsorption to soil that will attenuate volatilization(SRC). Dilauryl thiodipropionate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). A 57% of theoretical BOD using activated sludge in the Japanese MITI test(3) suggests that biodegradation may be an important environmental fate process(SRC); although not classified as readily biodegradable (which requires a theoretical BOD of 60% or higher), dilauryl thiodipropionate is estimated to be inherently biodegradable(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 9X10+6(SRC), determined from a structure estimation method(2), indicates that dilauryl thiodipropionate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 4X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 21 and 160 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 60 years if adsorption is considered(4). According to a classification scheme(5), an estimated BCF of 15(SRC), from an estimated log Kow of 11.8(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A base-catalyzed second-order hydrolysis rate constant of 0.077 L/mole-sec(SRC) was estimated using a structure estimation method(6); this corresponds to half-lives of 2.8 years and 104 days at pH values of 7 and 8, respectively(SRC). A 57% of theoretical BOD using activated sludge in the Japanese MITI test(7) suggests that biodegradation may be an important environmental fate process(SRC); although not classified as readily biodegradable (which requires a theoretical BOD of 60% or higher), dilauryl thiodipropionate is estimated to be inherently biodegradable(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dilauryl thiodipropionate, which has an estimated vapor pressure of 3X10-8 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 dilauryl thiodipropionate 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 7.4 hours(SRC), calculated from its rate constant of 5.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase dilauryl thiodipropionate may be removed from the air by wet or dry deposition(SRC).

The CIR Expert Panel concludes that Dilauryl Thiodipropionate, Thiodipropionic Acid, Dicetyl Thiodipropionate, Dimyristyl Thiodipropionate, Distearyl Thiodipropionate, and Ditridecyl Thiodipropionate are safe as cosmetic ingredients in the practices of use and concentration given in this safety assessment when formulated to be non-irritating.

Safe for use in cosmetics, with qualifications

Using a structure estimation method based on molecular connectivity indices(1), the Koc of dilauryl thiodipropionate can be estimated to be 9X10+6(SRC). According to a classification scheme(2), this estimated Koc value suggests that dilauryl thiodipropionate is expected to be immobile in soil.

Dilauryl thiodipropionate's production and use as an antioxidant, additive for high-pressure lubricants and greases, plasticizer and softening agent, and antioxidant for edible fats and oils(1) may result in its release to the environment through various waste streams(SRC).

AEROBIC: Dilauryl thiodipropionate, present at 100 mg/L, reached 57% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(1); a theoretical BOD of 60% or higher indicates readily biodegradable(1). Although not classified as readily biodegradable, dilauryl thiodipropionate is estimated to be inherently biodegradable based on the data available(2).

An estimated BCF of 15 was calculated in fish for dilauryl thiodipropionate(SRC), using an estimated log Kow of 11.8(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Henry's Law constant for dilauryl thiodipropionate is estimated as 4X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dilauryl thiodipropionate is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 21 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 160 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 60 years if adsorption is considered(3). Dilauryl thiodipropionate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3X10-8 mm Hg(SRC), determined from a fragment constant method(1).

/LABORATORY ANIMALS: Acute Exposure/ Acute oral toxicity is ...slight for mice and rats which tolerate 1 g /kg doses of thiodipropionic acid and 2 g/kg doses of esters. Poorer tolerance for acid is at least partly due to its solubility in water and body fluids. With rats ... toxic when added to food in 3.0% concentration ... retarded growth... . /Thiodipropionic acid esters/

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Dogs were fed a mixture of 10 parts by weight of dilauryl thiodipropionate and one part of thiodipropionic acid in the diet at concentrations of 0.1% and 3.0% of the acid-ester mixture. No untoward effects were noted over a period of 100 days.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Thiodipropionic acid or its dilauryl or distearyl ester was fed to groups of 20 rats each at levels of 0%, 0.5%, 1.0% and 3.0% in the diet for a period of two years. No discernible adverse effects were observed in any of the experimental animals, as determined by growth rate, mortality, and pathological examination.

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ ADMIN UP TO 1600 MG/KG TO PREGNANT MICE FOR 10 CONSECUTIVE DAYS AND PREGNANT HAMSTERS FOR 5 DAYS HAD NO EFFECT ON NIDATION OR ON MATERNAL OR FETAL SURVIVAL.

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ ADMIN OF 1000 MG/KG TO PREGNANT RABBITS FOR 13 CONSECUTIVE DAYS HAD NO EFFECT ON NIDATION OR ON MATERNAL OR FETAL SURVIVAL.

The rate constant for the vapor-phase reaction of dilauryl thiodipropionate with photochemically-produced hydroxyl radicals has been estimated as 5.2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7.4 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.077 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 2.8 years and 104 days at pH values of 7 and 8, respectively(SRC).

According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of dilauryl thiodipropionate is 1000 or greater; the data may be greatly underestimated(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 18,006 workers (7,053 of these were female) were potentially exposed to dilauryl thiodipropionate in the US(1). Occupational exposure to dilauryl thiodipropionate may occur through dermal contact with this compound at workplaces where dilauryl thiodipropionate is produced or used. Dilauryl thiodipropionate's use as an antixidant in cosmetics(2) may expose the general population through dermal contact(SRC).

Dilauryl thiodipropionate's production and use as an antioxidant, additive for high-pressure lubricants and greases, plasticizer and softening agent, and antioxidant for edible fats and oils may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 3X10-8 mm Hg at 25 °C indicates dilauryl thiodipropionate will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase dilauryl thiodipropionate 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 7.4 hours. Particulate-phase dilauryl thiodipropionate will be removed from the atmosphere by wet or dry deposition. If released to soil, dilauryl thiodipropionate is expected to have no mobility based upon a an estimated Koc of 9X10+6. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 4X10-6 atm-cu m/mole and dilauryl thiodipropionate's strong adsorption to soil. A 57% of theoretical BOD using activated sludge in the Japanese MITI test suggests that biodegradation may be an important environmental fate process in soil and water. If released into water, dilauryl thiodipropionate is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 21 and 160 days, respectively. However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. An estimated BCF of 15 suggests bioconcentration in aquatic organisms is low. Hydrolysis is slow based on estimated hydrolysis half-lives of 2.8 years and 104 days at pH values of 7 and 8, respectively, at 25 °C. Occupational exposure to dilauryl thiodipropionate may occur through dermal contact with this compound at workplaces where dilauryl thiodipropionate is produced or used. The general population may be exposed through dermal contact from dilauryl thiodipropionate's use as an antioxidant in cosmetics and other consumer products. (SRC)

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

Specific prior-sanctioned food ingredients. Substances classified as antioxidants, when migrating from food-packaging material (limit of addition to food, 0.005%) shall include: ... dilauryl thiodipropionate.

This substance is generally recognized as safe for use in food when the total content of antioxidants is not over 0.02 percent of fat or oil content, including essential (volatile) oil content of the food, provided the substance is used in accordance with good manufacturing practice.

This substance is generally recognized as safe for use in food when the total content of antioxidants is not over 0.02 percent of fat or oil content, including essential (volatile) oil content of the food, provided the substance is used in accordance with good manufacturing or feeding practice.

LIKE THE ACID, LAURYL THIODIPROPIONATE IS ABSORBED FROM INTESTINAL TRACT OF DOG, RABBITS, & RAT, & LARGE PART IS ELIMINATED FROM BODY BY KIDNEYS, AS THIODIPROPIONIC ACID.

Dilauryl thiodipropionate (DLTDP), dicetyl thiodipropionate, dimyristyl thiodipropionate, distearyl thiodipropionate, and ditridecyl thiodipropionate are dialkyl esters of their respective alcohols and thiodipropionic acid (TDPA) used in cosmetics. Ingested DLTDP was excreted in the urine as TDPA. Single-dose acute oral and parenteral studies and subchronic and chronic repeated dose oral studies did not suggest significant toxicity. Neither DLTDP nor TDPA was irritating to animal skin or eyes and they were not sensitizers. TDPA was neither a teratogen nor a reproductive toxicant. Genotoxicity studies were negative for TDPA and DLTDP. Clinical testing demonstrated some evidence of irritation but no sensitization or photosensitization. The Cosmetic Ingredient Review Expert Panel considered that the data from DLTDP reasonably may be extrapolated to the other dialkyl esters and concluded that these ingredients were safe for use in cosmetic products that are formulated to be nonirritating.

LIKE THE ACID, LAURYL THIODIPROPIONATE IS ABSORBED FROM INTESTINAL TRACT OF DOG, RABBITS, & RAT, & LARGE PART IS ELIMINATED FROM BODY BY KIDNEYS, AS THIODIPROPIONIC ACID.

SINGLE ORAL DOSES IN RATS OF 1-(14)C DIDODECYL THIODIPROPIONATE (107 & 208 MG/KG) WERE RAPIDLY ELIMINATED, MOSTLY IN URINE (85-88%), WITH LESS IN FECES (1.8-3.5%) AND AS (14)CO2 (3-4%, BY DAY 4).

CIR ingredient: Dilauryl Thiodipropionate

Used as a stabilizer of food packaging films, an additive for high-pressure lubricants and greases, a plasticizer and softening agent, and an antioxidant for edible fats and oils (up to 0.02% oil content); [HSDB]

Thiosynergist for polyolefin stabilization.

Used as a secondary antioxidant in a variety of polymer systems including polyolefins, ABS, styrene-butadiene emulsions and certain adhesives. These antioxidants are added to help preserve the integrity of the plastics to which they are added. Common commercial products that may contain low levels of these antioxidants include household appliances such as coffee makers, food packaging trays like those found at the grocers, plastic patio furniture, and plastic covering for wire. In addition to these uses, dilauryl thiodipropionate is FDA approved for use in food-packaging under specific listings in the Code of Federal Regulations (CFR) Title 21-Food and Drugs Chapter I-Food and Drug Administration, Department of Health and Human Services, and DLTDP has both human and animal GRAS applications.

Antioxidant, additive for high-pressure lubricants and greases, plasticizer and softening agent, antioxidant for edible fats and oils (up to 0.02% oil content).

Antioxidant in cosmetics (use levels are normally about 0.1% and rarely exceed 0.2%)

2023: 850,000 - <1,000,000 lb

(1990) 694 t

Propanoic acid, 3,3'-thiobis-, didodecyl ester 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).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#1103]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Propanoic acid, 3,3'-thiobis-, 1,1'-didodecyl ester. Aggregated National Production Volume: 1 to < 10 million pounds.

/Dilaurylthiodipropionate/ (DLTDP) ... is produced by reacting ... thiodipropionitrile (TDPN) with ... lauryl alcohol. ... The reaction of TDPN with the alcohols is an esterification using acid catalysts (hydrochloric acid and sulfuric acid). Water is removed under vacuum to drive the esterification to completion. Then the catalyst is neutralized and salts and impurities removed in a series of filtrations and washes. The molten DLTDP ... are converted to solid products by flaking and packaged.

Fragrance Ingredients

Food Additives -> ANTIOXIDANT -> JECFA Functional Classes

Cosmetics -> Antioxidant

Soap, Cleaning Compound, and Toilet Preparation Manufacturing

Propanoic acid, 3,3'-thiobis-, 1,1'-didodecyl ester: ACTIVE

...SULFUR-CONTAINING COMPOUNDS, SUCH AS.. .DILAURYL-THIODIPROPIONATE, ARE APPROVED FOR USE IN EDIBLE FATS, BUT THEIR RELATIVE INEFFECTIVENESS HAS DISCOURAGED THEIR USE IN FOOD... SULFUR-CONTAINING COMPOUNDS OFTEN PRODUCE SOME ODOR & FLAVOR PROBLEMS IN MOST FOOD FATS.

...SULFUR-CONTAINING COMPOUNDS...ARE WIDELY USED...IN COMBINATION WITH PHENOLIC-TYPE ANTIOXIDANTS IN STABILIZATION OF SOME FOOD PACKAGING FILMS, PARTICULARLY POLYOLEFINS.