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Plates or needles, mp 169-171 °C. Specific optical rotation: -71 deg at 23 °C/D ( c = 1.1 in CHCl3), -88 deg at /546 (CHCl3) /Benzoate/

UV irradiation gives vitamin D4 ... Solvated needles from ethyl acetate + methanol, mp 152-153 °C (dried). Specific optical rotation: -109 deg at 19 °C/D (CHCl3); also reported as needles from chloroform-methanol, mp 128-130 °C; Specific optical rotation: -121 deg at 19 °C/D ( c = 0.1). UV max: 262,272,282,294 nm (epsilon 8000, 11200, 11800, 6800). /22,23-Dihydro analog/

Specific optical rotation: -135 deg (in chloroform)

Specific optical rotation: -135 deg at 20 °C/D ( c = 1.2 in CHCL3, calcd as anhydr); -171 deg at 20 °C/546

Solid; Turns yellow on exposure to light and air; [Merck Index] Hygroscopic solid; [Sigma-Aldrich MSDS]

Solid

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2.5X10+6(SRC), determined from a structure estimation method(2), indicates that ergosterol is expected to be immobile in soil(SRC). Volatilization of ergosterol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Ergosterol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.0X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). However, adsorption to soil is expected to attenuate volatilization(SRC). The soil microbe Nocardia erthopolis was able to grow on ergosterol(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.5X10+6(SRC), determined from a structure estimation method(2), indicates that ergosterol 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 1.6X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 9 hours and 11 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 2.1X10+4 years if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 1,600(SRC), from an estimated log Kow of 8.86(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC). Aquatic biodegradation data were not available(SRC, 2009).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ergosterol, which has an estimated vapor pressure of 1.0X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase ergosterol may be removed from the air by wet or dry deposition(SRC). When irradiated with uv light, ergosterol develops powerful vitamin D2 activity(5) and therefore the compound is expected to be susceptible to direct photolysis by sunlight(SRC).

Vitamin D is excreted into breast milk in limited amounts. A direct relationship exists between maternal serum levels of vitamin D and the concentration in breast milk. Chronic maternal ingestion of large doses may lead to greater than normal vitamin D activity in the milk and resulting hypercalcemia in the infant. /Vitamin D/

/AQUATIC SPECIES/ In crustaceans, cholesterol is an essential nutrient, which they must directly obtain from their food or by bioconversion from other dietary sterols. Eukaryotic phytoplankton contain a great variety of sterols that differ from cholesterol in having additional substituents or different positions and/or number of double bonds in the side chain or in the sterol nucleus. ... This study ... investigated to what extent these structural features affect the growth and reproduction of Daphnia galeata in standardized growth experiments with the cyanobacterium Synechococcus elongatus supplemented with single sterols as food source. The results indicated that delta 5 (sitosterol, stigmasterol, desmosterol) and delta 5.7 (7-dehydrocholesterol, ergosterol) sterols meet the nutritional requirements of the daphnids, while the delta 7 sterol lathosterol supports somatic growth and reproduction to a significantly lower extent than cholesterol. Dihydrocholesterol (delta 0) and lanosterol (delta 8) did not improve the growth of D. galeata, and growth was ad versely affected by the delta 4 sterol allocholesterol. Sterols seem to differ in their allocation to somatic growth and reproduction. Thus, structural differences of dietary sterols have pronounced effects on life-history traits of D. galeata.

The ergosterol weighted-average concentration in fungal spores commonly encountered in subtropical ambient air was 0.191 pg/spore(1). The ergosterol content in 20 white-rot fungi isolates ranged from 2,380 to 13,060 ug/g fungal biomass, with Bjerkandera adusta 4,312, Coriolopsis gallica 8,260, and Phanerochaete chyrosporium 3,642 ug/g fungal biomass reported as examples(2). Ergosterol content was shown to be affected negatively by the amount of pollutants present(2). Ergosterol has also been identified in a variety of fungi associated with food spoilage molds(3).

Ergosterol concentrations in digested sludges collected from four French municipal wastewater treatment plants in Lyon (Saint Fons, 11/18/1993) and Paris (Asnieres/Oise, 8/26/1991; Acheres, 1/26/1993; Evry 6/8/1993) were at <0.1, <0.1, <0.1, and 0.02 mg/g dried matter, respectively(1).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of ergosterol can be estimated to be 2.5X10+6(SRC). According to a classification scheme(2), this estimated Koc value suggests that ergosterol is expected to be immobile in soil.

RURAL/REMOTE: The ergosterol concentration in subtropical air from an unspecified location was estimated as approximately 230 pg/sq m(SRC), based upon the weighted-average concentration in fungal spores commonly encountered in subtropical ambient air of 0.191 pg/spore(1).

/SIGNS AND SYMPTOMS/ Initial...symptoms of vitamin D toxicity are...associated with hypercalcemia and consist in weakness, fatigue, lassitude, headache, nausea, vomiting, and diarrhea. Early impairment of renal function...manifest by polyuria, polydipsia, nocturia, decreased urinary concentrating ability and proteinuria. /Vitamin D/

/SIGNS AND SYMPTOMS/ With prolonged hypercalcemia there may be deposition of calcium salts in soft tissues, most significantly within kidney.../resulting/ in nephrolithiasis, diffuse nephrocalcinosis, or both. Other sites of calcification may include blood vessels, heart, lungs, and skin. /Vitamin D/

/SIGNS AND SYMPTOMS/ Some individuals exhibit hypertension. ...Changes in blood chemistry are elevated concentrations of plasma calcium and nonprotein nitrogen; phosphate concentrations are variable. Mobilization of calcium from bone contributes to hypercalcemia and is...responsible for...osteoporosis in...hypervitaminosis D. /Vitamin D/

/SIGNS AND SYMPTOMS/ Vitamin D toxicity may be manifested in fetus. There is...relationship between excess maternal vitamin D intake or extreme sensitivity to vitamin and nonfamilial congenital supravalvular aortic stenosis. In infants, this anomaly is often found...with other stigmata of hypercalcemia. /Vitamin D/

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

... The metabolism of ergosterol by cytochrome P450scc /is demonstrated/ in either a reconstituted system or isolated adrenal mitochondria. The major reaction product was identified as 17alpha,24-dihydroxyergosterol. Purified P450scc also generated hydroxyergosterol as a minor product, which is probably an intermediate in the synthesis of 17alpha,24-dihydroxyergosterol. In contrast to cholesterol and 7-dehydrocholesterol, cleavage of the ergosterol side chain was not observed. NMR analysis clearly located one hydroxyl group to C24, with evidence that the second hydroxyl group is at C17. 17alpha,24-Dihydroxyergosterol inhibited cell proliferation of HaCaT keratinocytes and melanoma cells. Thus, in comparison with cholesterol and 7-dehydrocholesterol, the 24-methyl group and the C22-C23 double bond of ergosterol prevent side chain cleavage by P450scc and change the enzyme's hydroxylase activity from C22 and C20, to C24 and C17, generating bioactive product.

In order to investigate the effect of the different stereochemistry of C-24 on the microbial C-26 oxidation of sterol side-chain the genetically modified Mycobacterium sp. BCS 396 strain was used to transform erogsterol. Ergosterol was converted to 3-oxo-4,22-ergostadien-26-oic acid methyl ester, 3-oxo-1,4,22-ergostatrien-26-oic acid methyl ester, and 3-oxo-1,4,22-ergostatrien-26-oic acid, the structures of which have been determined by IR, 1H NMR, 13C NMR, and mass spectroscopy. The X-ray structure of 3-oxo-4,22-ergostadien-26-oic acid methyl ester revealed that oxidation at C-26 of the ergostane side-chain generates a chiral center with S-configuration at C-25 as a result of chiral induction of the C-24 center.

The results of experiments on rats given the ergosterol-containing diet for a long time indicate that ergosterol was incorporated in liver tissues in trace amounts which are not comparable with ergosterol concentrations exerting an effect in model experiments. Ergosterol was not detected in the liver after 3-day experiments. At the same time it was established that the proportion of unchanged ergosterol in rat feces was about 16% of the amount administered per os. The products of a possible ergosterol transformation (dehydroneoergosterol-24-methyl-1,3,5 (10), 6,8 (9), 22-hexaen-3 beta-ol; 24-methylcholesta-7,24 (28)-dien-3 beta-ol; 4-cholesta-7,22,25 (?)-trien-3 beta-ol; 4-methylcholesta-7,22 (?)-dien-3 beta-ol, and so forth were identified in feces.

Metabolism of orally administered ergosterol (Erg) ... in rats and ... vitamin D biological activity were investigated. Most of orally administered Erg ... /was/ excreted in feces and the remaining sterols were absorbed through intestine. The absorbed sterols were not transported in skin as the intact forms but metabolized into brassicasterol and cholesterol, respectively, within 25 hr. Neither increment of intestinal calcium absorption nor plasma calcium concentrations were observed by oral administration of Erg ... to vitamin D-deficient rats...

The chick-oviduct assay was used to investigate the effects of dietary ergosterol on the response to oral progestogens and estrogens. Progestogens alone had no effect on the oviduct but the hypertrophy due to estrogen was greatly enhanced by simultaneous treatment with progestogen at all dose levels tested. Ergosterol had no effect on any of the responses of the oviduct studied.

Vitamin D is excreted into breast milk in limited amounts. A direct relationship exists between maternal serum levels of vitamin D & the concn in breast milk. Chronic maternal ingestion of large doses may lead to greater than normal vitamin D activity in the milk & resulting hypercalcemia in the infant. /Vitamin D/

The results of experiments on rats given the ergosterol-containing diet for a long time indicate that ergosterol was incorporated in liver tissues in trace amounts which are not comparable with ergosterol concentrations exerting an effect in model experiments. Ergosterol was not detected in the liver after 3-day experiments. At the same time it was established that the proportion of unchanged ergosterol in rat feces was about 16% of the amount administered per os. The products of a possible ergosterol transformation (dehydroneoergosterol-24-methyl-1,3,5 (10), 6,8 (9), 22-hexaen-3 beta-ol; 24-methylcholesta-7,24 (28)-dien-3 beta-ol; 4-cholesta-7,22,25 (?)-trien-3 beta-ol; 4-methylcholesta-7,22 (?)-dien-3 beta-ol, and so forth were identified in feces.