Docosanoic acid

340.58

340.58

1792887

204-010-8

H390488X0A

32364

DTXSID3026930

C68322

Waxy solid|Needles

2915900090

37.3

9.6

White to slightly yellow Crystalline Powder

0.8221 g/cm³ @ Temp: 100 °C

79.95 °C

306 °C @ Press: 60 Torr

306°C/60mm

1.459

soluble in DMF (~3 mg/ml), hot methanol, water (0.15 mg/ml at 25°C), chloroform, and ethanol (2.18 mg/ml at 25°C).chloroform: soluble 50mg/mL, clear

2-8°C

7.15X10-8 mm Hg at 25 deg C (est)

Henry's Law constant = 1.58X10-4 atm-cu m/mole at 25 °C (est)

191.18 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

Neutralization value: 164.73|mp 54 °C /Methyl ester/|mp 50 °C; bp 185 °C at 0.2 mm Hg /Ethyl ester/|mp 111-112 °C /Amide/|Hydroxyl radical reaction rate constant = 2.81X10-11 cu cm/molec-sec at 25 °C (est)

II

6.1

NONH for all modes of transport

-

36/37/38

26-36/37/39-24/25

Stable. Combustible. Incompatible with bases, oxidizing agents, reducing agents.

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

H315

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.|Dissolved or mixed the material with a combustible solvent and burned in a chemical incinerator equipped with an afterburner and scrubber.

Organization for Economic Cooperation and Development; Screening Information Data Set for Docosanoic acid (CAS #112-85-6) (November 6 - 9, 2001). Available from the Database Query page at: http://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html as of January 24, 2008.

Not Classified

Combustible

Water samples taken from the effluent of a kraft paper mill located on the shore of Lake Saimaa, Lappeenranta, Finland were found to contain docosanoic acid concns ranging from 1 to 37 ug/L over a 9 day period(1). Docosanoic acid was identified in a tire manufacturing plant wastewater at 1 mg/L(2).|Docosanoic acid was found in candle smoke from paraffin and beeswax at 0.15 and 1.21 mg/g of organic compounds(1). Docosanoic acid was found in wood smoke from yellow poplar, white ash, sweet gum, mockernut hickory, loblolly pine, and slash pine(2). Docosanoic acid was detected in wood smoke from pine, oak and synthetic logs at 7.98, 4.63 and 0.99 mg/kg of wood burnt(3). Docosanoic acid was found at 20.8, 7.61 and 5.09 mg/kg of burnt pine, oak and eucalyptus wood, respectively, in the particulate phase(4). Docosanoic acid was found in extract from a pine wood burning campfire at 628 ng/g(5). Docosanoic acid was found at 17 ug/g from heated roofing tar pot fumes(6).|Docosanoic acid was not detected in tire wear particles, and in brake lining particles and road dust particles at concns of 2.1 ug/g and 70.2 ug/g of particle sample, respectively(1). Docosanoic acid was emitted at 350 ug/kg of cooked meat in the particulate phase(2). Fine particle emission of docosanoic acid from a natural gas-fired water heater and a natural gas-fired space heater were not detected(3).

SEDIMENT: Docosanoic acid was identified in sediment samples taken Sept 1995 at the mouth of 3 rivers and in 1 port in Niigata, Japan(1). Sediment samples from the Tarawera River in the Eastern Bay of Plenty region, New Zealand were found to contain an average of 15.5 ppm of docosanoic acid(2).

URBAN/SUBURBAN: Sampling of particulate matter and gaseous pollutants was conducted for three weeks between October 7 and 29, 1976 in Belgium; docosanoic acid was identified in particulate samples with an average concn of 13.68 ug/1000 cu m(1). Aerosol samples collected in the Tsukuba area, northeast of Tokyo, Japan on April 28-29, 1985 contained docosanoic acid in unknown concns(2). Aerosol samples were collected systematically throughout a complete annual cycle (1982) at four urban sites in southern California. Ambient annual concns of docosanoic acid ranged from 5.7 to 9.9 ng/cu m(3). Docosanoic acid had an average concentration of 2.6 ng/cu m in 4 urban sites from southern CA from samples taken Sept 8-9, 1993(4). A southern CA atmospheric study gave concns of docosanoic acid at 2.33, 5.41, 2.08, 2.01 and 2.8 ng/cu m for Long Beach, Mira Loma, Riverside, San Dimas and Upland, respectively(5). Docosanoic acid was found in atmospheric samples taken Dec 26-28, 1995 and Jan 4-6, 1996 in Fresno, CA at 160 and 48.1 ng/cu m and samples taken in Bakersfield had 43.1 and 53.6 ng/cu m, respectively(6). n-Docosanoic acid was found in atmospheric samples from North Birmingham, AL; Jefferson Street, Atlanta, GA; Gulfport, MS; Pensacola, FL; and OLF#8 (suburban site 20 km NW of downtown Pensacola), FL at concns of 4.12; 2.44; 1.60; 2.98; and 1.75 ng/cu m, respectively(7). Docosanoic acid was found in Antwerp, Belgium at concns of 3.2 to 8.4 ug/1000 cu m(8). Atmospheric concns of docosanoic acid in Algiers City, Algeria May 27 to Sept 2, 1998 averaged 4.7 ng/cu m(9).|RURAL/REMOTE: Docosanoic acid was found on aerosols obtained over the southern North Atlantic Ocean with a mean concn of 1.1 ng/cu m and over Chacaltaya, Bolivia with a mean concn of 0.49 ng/cu m(1). A southern CA atmospheric study gave concns of docosanoic acid as 1.14, 2.32, 5.28, 0.77, 1.72, 2.99 and 2.21 ng/cu m for Lompoc, Alpine, Atascadero, Lake Arrowhead, Lake Elsinore, Lancaster and Santa Maria, respectively(2). Atmospheric samples taken Dec 26-28, 1995 and Jan 4-6, 1996 in Kern Wildlife Refuge, CA had 4.10 and 4.30 ng/cu m of docosanoic acid(3). Docosanoic acid concns of 2.83, 2.02 and 2.59 ng/cu m were found in Centreville, AL, Yorkville, GA and Oak Grove, MS, respectively(4). Docosanoic acid was found in LaPaz, Bolivia at concns of 0.29 to 0.69 ug/1000 cu m(5). Docosanoic acid was found at San Nicolas Island July to Sept, 1982 at an average concn of 0.39 ng/cu m(6).

Docosanoic acid was found in unburned paraffin and beeswax at 0.15 and 3.34 mg/g of wax(1).

Oral LD50 value of docosanoic acid for rats is greater than 2,000 mg/kg. There are no available data for irritation and sensitization. In an oral study using the OECD combined repeated dose and reproductive/developmental toxicity test [OECD TG 422], docosanoic acid was administered to rats at doses of 0, 100, 300, 1,000 mg/kg/day for at least 42 days . No deaths occurred and also no substance related toxic effects were observed in any parameters. Therefore, the NOAEL is considered to be 1,000 mg/kg/day for both repeated dose toxicity and reproductive/developmental toxicity. The chemical was negative in both a bacterial mutation test [OECD TG 471, 472] and a chromosomal aberration test in vitro [OECD TG 473]. ... Acute toxicity values of docosanoic acid on alga (Selenastrum capricornutum), aquatic invertebrate (Daphnia magna) or fish (Oryzias latipes) are greater than its water solubility (0.016 mg/L). The NOEC in a 21-day reproduction test with Daphnia magna is also greater than its water solubility. No significant effects are observed in any tests conducted at extremely high concentrations by using dispersant under OECD test guidelines [TG201, 202, 203, 204, or 211]. There is information that some fatty acids with shorter carbon chain caused no mortality at saturated concentration in certain aquatic organisms (gammarus in freshwater; Medaka in seawater condition). Considering from these data and additional information, it is reasonable to assume that docosanoic acid is not toxic to aquatic organisms at the concentration less than its water solubility (0.016 mg/L). A PNEC is not calculated since NOEC values obtained are above the water solubility of the substance.

THE BLOOD PLATELET AGGREGATING EFFECT OF BEHENIC ACID ON WASHED PIG BLOOD PLATELETS WAS ENHANCED BY THE ADDITION OF CALCIUM IONS. LINOLENIC ACID COMPLETELY INHIBITED THE EFFECT OF BEHENIC ACID WHEN BOTH WERE ADDED IN EQUIMOLAR CONCENTRATIONS.

LD50 Rats oral >2,000 mg/kg /Purity 85.9 %; Impurities: (C14-C20) fatty acids 10.9 %, C24 fatty acid 2.3 %/

/AQUATIC SPECIES/ In a chronic toxicity test with Daphnia magna, conducted at 0.30, 0.55 and 1.00 mg/L under semi-static conditions (water renewal: 3 times a week), the measured concentrations in groups tested at 21 day were different over 20% from their corresponding nominal concentration. Thus, the concentrations were expressed using time-weighted averages: 0.24, 0.49 and 0.84 mg/L, respectively. The parental mortalities observed in controls and treated groups were within the range of 20% and no effects by dispersant were observed. EC50 and NOEC values in this chronic toxicity test to Daphnia magna on reproduction were greater than 0.84 mg/L.|/AQUATIC SPECIES/ Toxicity studies of docosanoic acid have been conducted using dispersant in a limited number of representative aquatic organisms: algae (Selenastrum capricornutum), aquatic invertebrates (Daphnia magna), and fish (Oryzias latipes) ... In all tests, no significant effect was observed at considerably higher concentration than its water solubility (0.016 mg/L).

Minor constituent of most seed fats, animal milk fats and marine animal oils.|Occurs in bean oil|THE HIGHEST CONCENTRATION OF BEHENIC ACID WAS FOUND IN GARCINIA MANGOSTANA AND VENTILAGO MADRASPATANA SEEDS.|BEHENIC ACID (2.62%) WAS ISOLATED FROM THE OIL OBTAINED FROM THE MEDICINAL PLANT ERYTHRINA SUBEROSA ROXB SEEDS.|Docosanoic acid is a carboxylic acid that is also known as a fatty acid because fatty acids were first isolated by the hydrolysis of naturally occurring fats(1). Fatty acids are widely distributed in nature as components of animal and vegetable fats(2) including lipids such as oils and fats, waxes, sterol esters and other minor compounds(1).

Docosanoic acid's production and use in cosmetics, waxes, plasticizers, chemicals and stabilizers(1) may result in its release to the environment through various waste streams(SRC).|Large amt (approx 50%) are found in (possibly hydrogenated ?) jamba oil, mustard seed oil and rape oil.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.4X10+5(SRC), determined from a structure estimation method(2), indicates that undissociated docosanoic acid is expected to be immobile in soil(SRC). The estimated pKa of docosanoic acid is 4.7(3), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the acid exists as an anion and anions do not volatilize(SRC). Docosanoic is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.1X10-8 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation of 69% of the theoretical BOD using a modified closed bottle Blok test employing a sewage inoculum incubated 28 days(6) suggests that biodegadation may be an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.4X10+5 for the free acid(SRC), determined from a structure estimation method(2), indicates that undissociated docosanoic acid is expected to adsorb to suspended solids and sediment(SRC). An estimated pKa of 4.7(3) indicates docosanoic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 9.91(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A half life of 1.7 days in freshwater after a 29 days(8) suggests that biodegradation may be an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), docosanoic acid, which has an estimated vapor pressure of 7.1X10-8 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 docosanoic acid 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 hours(SRC), calculated from its rate constant of 2.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase docosanoic acid may be removed from the air by wet or dry deposition(SRC). Docosanoic acid 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).

The rate constant for the vapor-phase reaction of docosanoic acid with photochemically-produced hydroxyl radicals has been estimated as 2.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 14 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Docosanoic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Docosanoic acid 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).

An estimated BCF of 3 was calculated in fish for docosanoic acid(SRC), using an estimated log Kow of 9.91(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).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of undissociated docosanoic acid can be estimated to be 1.4X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that docosanoic acid is expected to be immobile in soil(SRC). The estimated pKa of docosanoic acid is 4.7(3), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

An estimated pKa of 4.7(1) indicates docosanoic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(2). Docosanoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.1X10-8 mm Hg(SRC), determined from a fragment constant method(3).

Docosanoic acid was identified as a volatile component of roasted and boiled Chinese chestnuts (Castanea molissima)(1).

ENVIRONMENTAL: Docosanoic acid is found as a minor constituent of animal milk fats(1).

THE LONG CHAIN SATURATED MONOCARBOXYLIC ACIDS.../INCLUDING BEHENIC ACID/ ARE OF A VERY LOW ORDER OF TOXICITY AND NO PROBLEMS ARE LIKELY IN INDUSTRIAL USE.|NIOSH (NOES Survey 1981-1983) has statistically estimated that 5,191 workers (2,194 of these were female) were potentially exposed to docosanoic acid in the US(1). Occupational exposure to docosanoic acid may occur through dermal contact with this compound at workplaces where n-docosanoic acid is produced or used. Monitoring and use data indicate that the general population may be exposed to docosanoic acid via inhalation of ambient air, ingestion of food, and dermal contact with this compound and other consumer products containing docosanoic acid(SRC).

(C14-C20) fatty acids ca. 11 %; C24 fatty acid ca. 2 %

/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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Organic acids and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. 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 ... . 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. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/|/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. Early intubation, at the first sign of upper airway obstruction, may be necessary. 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 (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/

/HUMAN EXPOSURE STUDIES/ ... In a randomized, crossover, metabolic-ward study, 7 mildly hypercholesterolemic men were fed 3 natural-food diets supplemented with behenate oil, palm oil, or high-oleic acid sunflower oil. Mean serum lipid and lipoprotein concentrations and plasma triacylglycerol fatty acid composition were determined from fasting blood drawn during the final 4 days of each 3-wk diet period. ... Behenate oil produced mean concentrations of total cholesterol (5.87+/-0.8 mmol/L) and LDL cholesterol (4.40+/-0.8 mmol/L) not significantly different from those produced by palm oil (5.84+/-0.7 and 4.42+/-0.7 mmol/L, respectively) but significantly higher than those produced by high-oleic acid sunflower oil (5.12+/-0.5 and 3.70+/-0.6 mmol/L, respectively). There were no significant differences in triacylglycerol or HDL-cholesterol concentrations. ... /Behenate oil/|/CASE REPORTS/ A 53-year-old librarian had recurrent palpable purpura on her ankles and legs that was found to be caused by the fumes released from heat-activated photocopy paper at her place of employment. Behenic acid was identified as the responsible chemical component through a series of challenge studies that simulated her work exposure. Behenic acid, a fatty acid, is volatilized when heat-activated photocopy paper is developed. Absorption through the upper respiratory mucosa was the likely route of entry of this agent. The mechanism of this reaction is unclear. Skin biopsies, complement studies, and immune complex assays failed to confirm a type III immune response. /SRP: Results of this report has been questioned/

behenic acid

Grades: Technical, 99%

All other basic organic chemical manufacturing|Docosanoic acid: ACTIVE|Straight chain saturated fatty acid. /From table/

EIGHTY SPECIFIC COMPOUNDS WERE IDENTIFIED IN RAW AND TREATED WASTEWATER BY GAS CHROMATOGRAPHY/MASS SPECTROMETRY.|SOYBEAN OIL FATTY ACIDS DETERMINED BY HPLC.|THE FATTY ACID COMPOSITION OF ROOT OIL OF CURCULIGO ORCHIOIDES (USED MEDICINALLY IN INDIA) WAS DETERMINED BY TLC-GAS CHROMATOGRAPHY TECHNIQUES. BEHENIC ACID WAS A MAIN COMPONENT ACID.|BEHENIC ACID (2.62%) WAS ISOLATED FROM THE OIL OBTAINED FROM THE MEDICINAL PLANT ERYTHRINA SUBEROSA ROXB SEEDS AND IDENTIFIED BY THIN LAYER CHROMATOGRAPHY.

Analyte: behenic acid; matrix: blood (plasma); procedure: high-performance liquid chromatography with fluorescence detection at 360 nm (excitation) and 420 nm (emission); limit of detection: 50 ng

EPA Safer Chemical Functional Use Classes -> Surfactants|Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern|Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Straight chain fatty acids [FA0101]|Cosmetics -> Emulsifying