Tritriacontane

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.4X10+9(SRC), determined from a structure estimation method(2), indicates that tritriacontane is expected to be immobile in soil(SRC). Volatilization of tritriacontane from moist soil surfaces is expected(SRC) given an estimated Henry's Law constant of 3600 atm-cu m/mole(SRC), using a fragment constant estimation method(2). However, adsorption to soil is expected to attenuate volatilization(SRC). Tritriacontane is not expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of 4.02X10-11 mm Hg at 25 °C(3). Biodegradation oxygen consumption values of 8.2 and 7.6 ug/mL for analogous tetracosane (C24) and hexatriacontane (C36), respectively, using a soil suspension(4) indicate that biodegradation of tritriacontane may be a slow environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.4X10+9(SRC), determined from a structure estimation method(2), indicates that tritriacontane 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 3600 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 6.3 hours and 8.5 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 more than 2 years if adsorption is considered (4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 16.55(2), and a regression-derived equation(2) suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation oxygen consumption values of 8.2 and 7.6 ug/mL for analogous tetracosane (C24) and hexatriacontane (C36), respectively, using a soil suspension(6) indicate that biodegradation of hentriacontane may be a slow environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tritriacontane, which has an extrapolated vapor pressure of 4.02X10-11 mm Hg at 25 °C(2), is expected to exist solely in the particulate phases in the ambient atmosphere(SRC). Particulate-phase tritriacontane may be removed from the air by wet and dry deposition(SRC). Tritriacontane does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

IDENTIFICATION AND USE: Trtriacontane is a higher n-alkane containing 33 carbon atoms (C33). HUMAN EXPOSURE AND TOXICITY: A case report described human disorder characterized by the accumulation of plant long-chain n-alkanes in viscera of a human patient. Diffuse visceral granuloma containing lipophilic crystallized material showed the presence of long-chain n-alkanes including tritriacontane. Study of n-alkane distribution in patient tissues showed a major accumulation in lumbo-aortic lymph nodes, adrenal glands, lung and liver; significantly lower amounts were detected in myocardium and kidney, whereas no detectable level was found in brain. ANIMAL STUDIES: Tritriacontane can contribute to the "paraffin liver" in cows. The very large quantities of the abnormal substance in the cow livers indicate low toxicity, and evidently accumulation over long periods of time.

Tritriacontane was detected, not quantified in the tobacco leaf (Nivotiana tabacum; Solanaceae)1). /Tritriacontane/

n-Tritriacontane detections in plants used in food and medicinal applications(1).[Table#8391]

Using a structure estimation method based on molecular connectivity indices(1), the Koc of tritriacontane can be estimated to be 1.4X10+9(SRC). According to a classification scheme(2), this estimated Koc value suggests that tritriacontane is expected to be immobile in soil.

URBAN/SUBURBAN: Tritriacontane was detected in particulate air samples from Georgia Tech campus, GA at mean concentrations of 0.66 and 0.88 ng/cu m for summer 2005 and winter 2006, respectively(1). A mean tritriacontane concentration of approximately 5 ng/cu m was reported in the particulate phase of air samples collected in an urban and industrialized area in Prato, Italy during 2002(2). Tritriacontane concentration were 11.4 and 6.9 ng/cu m in particulate phase in the summer and winter, respectively; concentrations of 0.6 and 0.5 ng/cu m were detected in vapor phase in summer and winter, respectively; samples were collected in an urban area in Nagoya, Japan in 1991(3).

RURAL/REMOTE: Tritriacontane was detected in particulate air samples from a rural area of Yorkville, GA at mean concentrations of 0.11 and 0.52 ng/cu m for summer and winter, respectively(1).

SOURCE DOMINATED: Tritriacontane was detected in particulate air samples from an interstate highway in Georgia at a mean concentration of 1.48 and 1.40 ng/cu m for summer and winter, respectively(1). Tritriacontane was detected at 53-560 pg/cu m with a mean of 220 pg/cu m in particulate air samples collected near a highway in Raleigh, NC; concentrations in samples collected 275 meters from the highway contained 75-880 pg/cu m with a mean of 230 pg/cu m(2).

/CASE REPORTS/ This report deals with a new human disorder characterized by the accumulation of plant long-chain n-alkanes in viscera of a human patient. Lipid analysis of tissues from an adult male after sudden death (affected with diffuse visceral granuloma containing lipophilic crystallized material) showed the presence of abnormal compounds identified as long-chain n-alkanes with 29 (n-nonacosane), 31 (n-hentriacontane) and 33 carbons (n-tritriacontane). Study of n-alkane distribution in patient tissues showed a major accumulation in lumbo-aortic lymph nodes, adrenal glands, lung (the highest levels were found in lung granulomas) and liver; significantly lower amounts were detected in myocardium and kidney, whereas no detectable level was found in brain. On the basis of the structural composition and of the tissue distribution of the accumulated n-alkanes, their dietary (plant) origin and the pathophysiological mechanism of the storage are discussed.

AEROBIC: Oxygen consumption of 8.2 and 7.6 ug/mL over 10 days was reported for straight chain alkanes tetracosane (C24) and hexatriacontane (C36), respectively, using a soil suspension of Hudson-Collamer silt loam soil incubated in the dark at 25 °C(1). By analogy, these test results suggest that biodegradation rates are slow for long chain alkanes such as tritriacontane (C33) under these conditions(SRC).

PURE CULTURE: Using 5 different marine bacterial strains and 4 different nitrogen sources, biodegradation of petroleum oil was examined under aerobic conditions at 26 °C for 10 days. Data reported for hexacosane (C26), octacosane (C28), and triacontane (C30), which were present as components of the petroleum oil, indicatd that these compounds were degraded by 4 of 5 bacterial strains with certain nitrogen sources and consumption ranged from 5 to 96%(1). Other long chain alkanes like tritriacontane (C33) may behave similarly(SRC).

An estimated BCF of 3 was calculated in fish for tritriacontane(SRC), using an estimated log Kow of 16.55(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 tritriacontane is estimated as 3600 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that tritriacontane 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 6 hours(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 8 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The volatilization half-life from a model pond is greater than 2 years when adsorption is considered(3). Tritriacontane's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Tritriacontane is not expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of 4.02E-11 mm Hg at 25 °C(4).

/VETERINARY CASE REPORTS/ About 50 years ago crystalline deposits of a substance representing approximately 7% wet tissue weight and believed to be hentriacontane or a mixture of similar long-chain n-alkanes (30-34 carbon atoms) were detected in two discolored and swollen cow livers. Stored purified extracts from these livers were recently reanalyzed using gas chromatography and mass spectrometry. They were found to contain about equal amounts of nonacosane and hentriacontane with a small admixture of tritriacontane and other long carbon-chain alkanes. On the basis of histological findings, five additional cases of "paraffin liver" in cows have been recorded. In the discussion comparison is made with the only known case of a similar disorder in a human, visceral accumulation of the same three alkanes as in the cows, which was recently described in the literature. Concerning the origin of the deposits, importance is given to the fact that the long-chain alkanes with odd carbon numbers identified both in cattle and man predominate in the cuticular waxes of many dietary plants. The very large quantities of the abnormal substance in the cow livers indicate low toxicity, and evidently accumulation over long periods of time.