Stigmasterol
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Stigmasterol
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CAS No:
83-48-7
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Formula:
C29H48O
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Chemical Name:
Stigmasterol
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Synonyms:
Stigmasta-5,22-dien-3-ol,(3β,22E)-;Stigmasta-5,22-dien-3β-ol;(3β,22E)-Stigmasta-5,22-dien-3-ol;Stigmasterol;Stigmasterin;24-Ethyl-5,22-cholestadien-3β-ol;β-Stigmasterol;(24S)-24-Ethylcholesta-5,22-dien-3β-ol;(24S)-5,22-Stigmastadien-3β-ol;Δ5,22-Stigmastadien-3β-ol;Δ5-Stigmasterol;(24S)-Stigmast-5,22-dien-3β-ol;NSC 8095;24β-Ethyl-5,22-cholestadien-3β-ol;Stigmasta-5,22(E)-dien-3β-ol;37571-80-5;203395-58-8;290307-81-2;1105699-57-7
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CAS No:
Description
Stigmasterol is a plant sterol which has been focused on the cholesterol-lowering activity and is valued as an anti-stiffness factor in the therapy of rheumatic diseases.
Characteristics
20.23000
7.80080
white solid
1.070 g/cm3 (20ºC)
170 °C
305ºC
219.4±13.7 °C
1.60 (20ºC)
H2O: insoluble
0-6ºC
1.62X10-10 mm Hg at 25 deg C (est)
Henry's Law constant = 2.59X10-4 atm-cu m/mol at 25 °C (est)
MP: 144 °C. Specific optical rotation: -55.6 deg( c = 2 in chloroform) /Acetate/|MP: 203 °C. Specific optical rotation: -13 deg ( c = 2 in alcohol) /p-Nitrobenzoate/|Hydroxyl radical reaction rate constant = 1.85X-10 cu cm/molec-sec at 25 °C (est)
Safety Information
UN 1888 6.1/PG 3
3
R22
S24/25
Xn; Xi
Stable under normal temperatures and pressures.
P201-P261-P304 + P340 + P312-P305 + P351 + P338-P308 + P313-P403 + P233
H302-H315-H319-H331-H336-H351-H361d-H372
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Estimated concentrations of stigmasterol in effluent from three publicly-owned treatment plants in New Jersey were reported as 0.7 and 0.2 ppb in one plant, not detected in a second plant and 1.3 ppb in the third plant(1). Stigmasterol 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, 0.08, 0.06, and 0.17 mg/g dried matter, respectively(2).
SEDIMENT: Stigmasterol levels in sediment from 5 sites within the Lagoon in Venice, Italy were 0.283, 0.344, 0.518, 0.158, 0.865 and 0.065 (ug/g dry weight) from Porto Marghera, Palude di Cona, Canal Grande, Sacca Sessola, Chioggia Basin, and an Adriatic Sea sample outside the lagoon, respectively(1).
URBAN/SUBURBAN: Stigmasterol levels in the ambient atmosphere of Bakersfield and Fresno in the San Joaguin Valley, CA were 2.0 ng/cu m and not detected, respectively, sampled from Dec 5, 1995 to Jan 6, 1996(1).|RURAL/REMOTE: Stigmasterol was not detected in the ambient atmosphere of Kern Wildlife Refuge in the San Joaquin Valley, CA, sampled from Dec 5, 1995 to Jan 6, 1996(1).|SOURCE DOMINATED: Stigmasterol concentrations in fine particle emissions were 0.789, 0.256, 0.055, 0.145, and 0.587 mg/g organic carbon emitted from fireplace combustion of northern red oak, paper birch, eastern white pine, eastern hemlock, and balsam, respectively(1). It was not detected in emissions from red maple(1). The concentration in wood smoke was 0.6 ug/g oak burned; it was not detected in smoke from eucalyptus nor pine(2). The relative concentration in smoke from burning needles, twigs, branches and wood of dead and dry pine (Pinus elliottii, var. densa) was 40 ng/g total extract(3). It was not detected in a study of six fine (foliar) fuels common to fire-prone US ecosystems typified by Aceraceae (Acer spp.), Fagaceae (Quercus sp.), Pinaceae (Pinus so., Tsuga sp.), Poazeae (Gentiana sp.), and Palmae (Sabal sp.)(4).
The average stigmasterol concentration in particulate phase tobacco smoke generated from Kentucky reference cigarettes was 2.9 umol/g(1). A concentration of 12.1 umol compound/mol CO has also been reported in tobacco smoke particles(2).
Toxicity
Stigmasterol is a plant sterol from soy and calabar beans(1).
Stigmasterol's production and use as a pharmaceutical and steroid intermediate(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5.4X10+5(SRC), determined from a structure estimation method(2), indicates that stigmasterol is expected to be immobile in soil(SRC). Volatilization of stigmasterol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.6X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Stigmasterol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.6X10-10 mm Hg(SRC), determined from a fragment constant method(4). A half-life in polluted river water of 17 days(5) suggests that the compound may biodegrade slowly in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5.4X10+5(SRC), determined from a structure estimation method(2), indicates that stigmasterol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected to be important(3) based upon an estimated Henry's Law constant of 2.6X10-4 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 13 hours and 10 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 6.1X10+4 years if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 850(SRC), from an estimated log Kow of 9.43(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). A half-life in polluted river water of 17 days(9) suggests that the compound may biodegrade slowly in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), stigmasterol, which has an estimated vapor pressure of 1.6X10-10 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 stigmasterol may be removed from the air by wet or dry deposition(SRC). Stigmasterol 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).
Stigmasterol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). Stigmasterol does not contain chromophores that absorb at wavelengths >290 nm(1) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 850 was calculated in fish for stigmasterol(SRC), using an estimated log Kow of 9.43(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of stigmasterol can be estimated to be 5.4X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that stigmasterol is expected to be immobile in soil.
The Henry's Law constant for stigmasterol is estimated as 2.6X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that stigmasterol 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 13 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 10 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 about 6.14X10+4 years when adsorption is considered(4). Stigmasterol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.6X10-10 mm Hg(SRC), determined from a fragment constant method(3).
SEAWATER: The mean concentration of stigmasterol in deposition zones of the north west Mediterranean Sea was 269.9 ng/g(1).|RAIN/SNOW/FOG: Stigmasterol was detected at concentrations of 0.34-0.16 ug/cu m-day in rain; collected over variable 11-25 day periods from 10/77-10/78 in urban Tokyo, Japan(1).
Stigmasterol levels in the crude vegetable oils(1). [Table#7341]
Occupational exposure to stigmasterol may occur through inhalation and dermal contact with this compound at workplaces where stigmasterol is produced or used. Monitoring data and use information indicate that the general population may be exposed to stigmasterol via inhalation of ambient air and wood smoke, and ingestion of certain vegetable oils containing stigmasterol. (SRC)
Drug Information
/EXPL/ ... The primary aim of this study was to determine the efficacy of a low-fat spread enriched with plant sterols in reducing total and low density lipoprotein-cholesterol (LDL-C) concentrations in primary hypercholesterolemia. The secondary objective was to evaluate whether patients receiving a lipid-lowering drug (fibrate) might differ in their response to plant sterols. The study was a randomized, double-blind, placebo-controlled two-period cross-over trial with two treatments and three periods. Both treatment periods lasted 2 months, with a washout period (2 months) between them. Spread enriched with plant sterols was compared to non-enriched control spread. Fortified fat spread provided 1.6 g/day of plant sterols derived from edible vegetable oils and fatty acids from sunflower seed oil. The plant sterol content consisted of sitosterol esters (50%), campesterol esters (25%), stigmasterol esters (20%) and 10% of other esters. Data in 53 hypercholesterolemic patients (31 females and 22 males) who completed the study were as follows: patients were 58+/-12 years of age with mean body mass index 23.5+/-2.8 kg/m2 (mean+/-SD). No adverse side-effects of the diet were reported. Plasma total cholesterol and LDL-C concentrations were significantly reduced by 6.4% and 8.8%, respectively, after using the spread enriched in plant sterols, as compared to controls (0.0% and 1.3%, respectively). No effect on high density lipoprotein-cholesterol (HDL-C) and lipoprotein(a) concentrations was detected. When subjects were divided in two subgroups according to fibrate treatment, supplementation with phytosterols decreased plasma cholesterol and LDL-C by 8.5% and 11.1%, respectively in the subgroup of patients treated with fibrates... /It was concluded/ that phytosterol-enriched spread is a useful adjunctive therapy for hypercholesterolemic patients.|/EXPL/ The commonly consumed plant sterols are sitosterol, stigmasterol and campesterol which are predominantly supplied by vegetable oils. ... The nutritional interest derives from the fact that the sterols have a similar structure to cholesterol, and have the capacity to lower plasma cholesterol and LDL cholesterol. Since the morbidity and mortality from cardiovascular disease have been dramatically reduced using cholesterol-lowering drugs (statins), the interest in plant sterols lies in their potential to act as a natural preventive dietary product.|/EXPL/ A study was conducted in 12 healthy males and 12 healthy females (mean age 36 years, mean body mass index 24 kg/m2), to determine the effect of a margarine enriched with phytosterol esters on fecal short-chain fatty acids (SCFAs) and fecal bacterial enzyme activities, viable fecal microflora count, female sex hormones and serum cholesterol concentrations. The study design was a two-period, parallel dosing, randomized, placebo-controlled dietary study. Under controlled dietary conditions, participants consumed 40 g of the control margarine for 21 and 28 consecutive days for males and females, respectively. This was followed immediately by the second part of the study where subjects were equally and randomly allocated to consume daily 40 g of either the control or the test margarine, containing 8.6 g vegetable oil phytosterols (a mixture of beta-sitosterol, campesterol and stigmasterol), also for 21 or 28 days. All females were shown to have a regular menstrual cycle and were on an established method of contraception not involving oral contraceptives. When compared with the control group values, the test group showed a significant reduction in serum total and LDL cholesterol concentrations of 18 and 23% (P < 0.001; P < 0.001) respectively, in fecal lactic acid concentration (P = 0.039) and in serum progesterone levels (P = 0.021). There were no other significant treatment effects. Within each group a number of significant changes occurred compared to baseline. In the test group, fecal lactic acid concentration and the ratio of acetic acid:total SCFA; and the ratio of butyric acid:total SCFA, in the control group were both significantly reduced (P = 0.016). Compared to baseline, azo-reductase activity was significantly reduced in the control group (P = 0.047). Total fecal aerobes (P = 0.028), lactobacilli (P = 0.003) and staphylococci (P = 0.025) content was also significantly reduced in the control group, while in the test group only lactobacilli content was reduced (P = 0.019). Of the significant findings reported in this study, none was considered to be of biological importance except the beneficial reduction in serum total and LDL-cholesterol concentrations...
... Metabolism of plant sterols and squalene administered intravenously in the form of lipid emulsion mimicking chylomicrons (CM) /was studied/. The CM-like lipid emulsion was prepared by dissolving squalene in commercially available Intralipid. The emulsion was given as an intravenous bolus injection of 30 mL containing 6.3 mg of cholesterol, 1.9 mg of campesterol, 5.7 mg of sitosterol, 1.6 mg of stigmasterol, 18.1 mg of squalene, and 6 g of triglycerides in six healthy volunteers. Blood samples were drawn from the opposite arm before and serially 2.5 -180 min after the injections. The decay of CM squalene, plant sterols, and triglycerides was monoexponential. The half-life of CM squalene was 74 +/- 8 min, that of campesterol was 37 +/- 5 min (P < 0.01 from squalene), and those of sitosterol, stigmasterol, and triglycerides were 17 +/- 2, 15 +/- 1, and 17 +/- 2 min, respectively (P < 0.01 from squalene and campesterol). The CM squalene concentration still exceeded the baseline level 180 min after injection (P = 0.02), whereas plant sterols and triglycerides returned to the baseline level between 45 and 120 min after injection. The half-lives of squalene and campesterol were positively correlated with their fasting CM concentrations. In addition, VLDL squalene, campesterol, and triglyceride concentrations, VLDL, LDL, and HDL sitosterol concentrations, as well as VLDL and LDL stigmasterol concentrations were increased significantly...|Rats were dosed by oral gavage with 14C-labelled samples of cholesterol, beta-sitosterol or beta-sitostanol or (3)H-labelled samples of beta-sitostanol, campesterol, campestanol or stigmasterol dissolved in sunflower seed oil. Urine and feces were collected for up to 96 hours after dosing. ... Animals were sacrificed and either prepared for whole body autoradiography or tissues and carcass remains were assayed for 14C or (3)H. The overall absorption of phytosterols was low as judged by tissue and carcass levels of radioactivity. Elimination from the body was mainly in the feces and was initially very rapid, but traces of material were still being excreted at 4 days after dosing. While total absorption of the phytosterols could not be fully quantified without biliary excretion data, it was clear that cholesterol was absorbed to the greatest extent (27% of the dose in females at 24 hours). Campesterol (13%) was absorbed more than beta-sitosterol and stigmasterol (both 4%) which were absorbed more than beta-sitostanol and campestanol (1-2%). The absorption of phytosterols was slightly greater in females than males. For each test material, the overall pattern of tissue distribution of radioactivity was similar, with the adrenal glands, ovaries and intestinal epithelia showing the highest levels and the longest retention of radioactivity.|Intestinal absorption of cholesterol, campesterol, campestanol, stigmasterol and sitosterol were measured in 10 healthy subjects by an intestinal perfusion technique over a 50 cm segment of the upper jejunum using sitostanol as non-absorbable marker. Cholesterol absorption was highest and averaged 33%., whereas the absorption rate of sitosterol averaged 4.2% and of stigmasterol 4.8%....|To study the effects of dietary stigmasterol on sterol and bile acids metabolism, Wistar rats were fed diets containing various amounts of stigmasterol. Feeding high stigmasterol doses (11, 26 or 52 mg/day) led to increased cholesterol, coprostanol and bile acid output. These effects were dose-dependent, and likely to be related to the inhibitory effect of plant sterols on cholesterol absorption. Moreover, it accounts for the beneficial effect of the stigmasterol on cholesterol lowering.|Tobacco sterols (cholesterol, beta-sitosterol, campesterol, and stigmasterol) are present in tobacco smoke and appear in plasma of mammals exposed to cigarette smoke. Because tobacco sterols may be important in the pathogenesis of smoking-induced lung and vascular diseases, ... the pattern of deposition of cigarette sterols in the lungs and appearance of cigarette sterols in plasma and body organs of rats /were studied/. After exposure to twenty 5 mL "puffs" of smoke from tobacco labeled with [4-14C]cholesterol or beta-[4-14C]sitosterol, rats were killed just after exposure (day 0) and on days 2, 5, 8, 11, 15, and 30, and the lungs and selected body organs analyzed for activity. ... Cigarette sterols /were/ associated with particulates in cigarette smoke, deposited mostly in distal airspaces and parenchyma of the lungs, and appear in plasma and several body organs for more than 30 days after this single exposure to cigarette smoke. Bronchoalveolar lavage fluid contained relatively small amounts of radiolabel for only the first few days, suggesting that most of the sterols were rapidly incorporated in lung parenchyma...
Metabolism of phytosterols was investigated using rat feces and liver microsomes. Feces were collected after phytosterols (a well characterized mixture of beta-sitosterol 40%, campesterol 30% and dihydrobrasicasterol) were administered orally (0.5 g/kg) to rats. Metabolites of phytosterols were identified using GC/MS. Three peaks were eluted at 12.47, 12.65, 12.87 min and had characteristic molecular ions m/z 428, 430, 432, respectively. Three fecal metabolites were identified as androstadienedione, androstenedione, and androstanedione. No metabolites could be detected in the rat liver microsomal reaction mixture. The results suggest that the metabolites of phytosterols in rat feces are formed by oxidation at 3- position, saturation at 5- and 6- position, and 17- side chain cleavage in the rat large intestine.|Plant sterols are an essential component of the membranes of all eukaryotic organisms. They are either synthesized de novo or taken up from the environment. Their function appears to be to control membrane fluidity and permeability, although some plant sterols have a specific function in signal transduction. The phytosterols are products of the isoprenoid pathway. The dedicated pathway to sterol synthesis in photosynthetic plants occurs at the squalene stage through the activity of squalene synthetase. Although the activity of 3-hydroxymethyl-3-glutaryl coenzyme A (HGMR) is rate-limiting in the synthesis of cholesterol, this does not appear to be the case with the plant sterols. Up-regulation of HGMR appears to increase the biosynthesis of cycloartenol but not the delta5-sterols. A decline in sterol synthesis is associated with a suppression of squalene synthetase activity, which is probably a critical point in controlling carbon flow and end-product formation. The major post-squalene biosynthetic pathway is regulated by critical rate-limiting steps such as the methylation of cycloartenol into cycloeucalenol. Little is known about the factors controlling the biosynthesis of the end-point sterol esters or stanols.
/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/
/HUMAN EXPOSURE STUDIES/ A study was conducted in 12 healthy males and 12 females (mean age 36 years) to assess the impact of a margarine enriched with phytosterol esters on fecal concentrations of bile acids and sterols. During the run-in period, volunteers consumed 40 g of a control margarine for 21 consecutive days if male, and for 28 days if female. Half of the volunteers were then randomly allocated to consume the control margarine for another 21 or 28 days, respectively. The remaining subjects consumed 40 g of a margarine containing 8.6 g vegetable oil phytosterol (46% (w/w) beta-sitosterol, 26% campesterol, 20% stigmasterol). Throughout the total study subjects consumed the same diet adjusted for individual energy requirements. The phytosterol ester-enriched spread significantly enhanced fecal neutral sterol concentrations from about 40 mg/g to 190 mg/g dry weight faeces. Fecal neutral sterol metabolites increased from about 30 mg/g to about 50 mg/g. The major parent sterols excreted were cholesterol, sitosterol, campesterol and stigmasterol. Sitosterol, campesterol and stigmasterol comprised 28%, 15% and 12% of the total fecal neutral sterols, reflecting the composition of the sterol enriched margarine. The major sterol metabolites excreted were metabolites formed by, predominantly, oxidation at the 3-position and metabolites saturated at the 5,6 position in a beta-configuration. Fecal secondary bile acid concentration was reduced by vegetable oil sterols from 7.6 mg/g dry faeces to 6.0 mg/g. Consumption of vegetable oil phytosterols slightly but significantly increased the fecal concentration of 4-cholesten-3-one. However, 4-cholesten-3-one concentration remained very low (less than 2 mg/g) and in line with values reported in the literature for subjects fed high or low fat diets. No sterol oxides could be detected in the feces...|/HUMAN EXPOSURE STUDIES/ ... To compare effects on plasma total-, LDL-, and HDL-cholesterol concentrations of margarines enriched with different vegetable oil sterols or sitostanol-ester.... A randomized double-blind placebo-controlled balanced incomplete Latin square design /study/ with five treatments and four periods of 3.5 weeks /was conducted/. Margarines enriched with sterols from soybean, sheanut or ricebran oil or with sitostanol-ester were compared to a non-enriched control margarine. Sterol intake was between 1.5-3.3 g/d. Two thirds of the soybean oil sterols were esterified to fatty acids. ... One hundred healthy non-obese normocholesterolaemic and mildly hypercholesterolemic volunteers aged 45+/-12.8 y, with plasma total cholesterol levels below 8 mmol/L at entry /were recruited/. Plasma lipid, carotenoid and sterol concentrations, blood clinical chemistry and hematology, fatty acid composition of plasma cholesterylesters and food intake /were measured/. Ninety-five volunteers completed the study. None of the margarines induced adverse changes in blood clinical chemistry, serum total bile acids or haematology. Plasma total- and LDL-cholesterol concentrations were significantly reduced by 8-13% (0.37-0.44 mmol/L) compared to control for margarines enriched in soybean oil sterol-esters or sitostanol-ester. No effect on HDL-cholesterol concentrations occurred. The LDL- to HDL-cholesterol ratio was reduced by 0.37 and 0.33 units for these margarines, respectively. Effects on blood lipids did not differ between normocholesterolemic and mildly hypercholesterolemic subjects. Plasma sitosterol and campesterol levels were significantly higher for the soybean oil sterol margarine and significantly lower for the sitostanol-ester margarine compared to control. Dietary intake was very similar across treatments. The fatty acid composition of plasma cholesterylesters confirmed the good compliance to the treatment. All sterol enriched margarines reduced lipid-standardized plasma alpha- plus beta-carotene levels. Plasma lycopene levels were also reduced but this effect was not significant for all products. ...|/CASE REPORTS/ Phytosterolemia (sitosterolemia) is a very rare inherited sterol storage disease characterized by tendon and tuberous xanthomas and by a predisposition to atherosclerosis. ... The 14-year-old female patient was found to have markedly elevated circulating levels of plant sterols (sitosterol, sitostanol, campesterol, stigmasterol), and the levels of these sterols were 20-50 times higher than in her healthy sister and heterozygous parents. In addition to the usual serum plant sterols ... a new major sterol in the patient tentatively identified as episterol or fecosterol (24-methyliden-cholest-7 (or 8)-en-3 beta-ol) /was found/. A newly developed method based on the use of deuterium labelled cholesterol and plant sterols was used to measure sterol absorption in the patient and her relatives. Absorption of sitosterol averaged 20% in the patient and ranged from 4 to 8% in the relatives. Absorption of campesterol averaged 31% in the patient and ranged from 15 to 18% in her relatives. Absorption of cholesterol averaged 63% in the patient and ranged from 35 to 45% in the relatives. Cholesterol synthesis appeared to be reduced in the patient and was 46-52% of that of her relatives.|/EPIDEMIOLOGY STUDIES/ ... A case-control study /was conducted/ of diet and ovarian cancer in western New York involving 124 primary, histologically confirmed ovarian cancer cases and 696 population-based controls, frequency matched to cases on age and county of residence. Diet was assessed with a detailed food-frequency questionnaire. Nutrient and phytochemical intakes were calculated from published food composition data. The odds ratios (OR) and 95% CI for risk of ovarian cancer with each nutrient, phytochemical and food group were estimated with unconditional logistic regression adjusting for age, education, total months menstruating, difficulty becoming pregnant, oral contraceptive use, menopausal status and energy intake. Compared with women in the lowest quintile of intake, reduced risks were observed for women in the highest quintile of intake of dietary fiber (OR 0.43, 95% CI, 0.20-0.94), total carotenoids (OR 0.33, 95% CI, 0.16-0.68), stigmasterol (OR 0.42, 95% CI, 0.20-0.87), total lignans (OR 0.43, 95% CI, 0.21-0.85), vegetables (OR 0.47, 95% CI, 0.23-0.97) and poultry (OR 0.45, 95% CI, 0.22-0.92). These results support a protective effect on ovarian cancer of phytoestrogen intakes and ... support the hypothesis that a plant-based diet may be important in reducing risks of hormone-related neoplasms.|For more Human Toxicity Excerpts (Complete) data for STIGMASTEROL (10 total), please visit the HSDB record page.
Stigmasterol Use and Manufacturing
Usually isolated from the phytosterol mixture from soy or calabar beans
Used as a precursor in the manufacture of synthetic progesterone.
Stigmasterol occurs with beta-sitosterol at a concentration of 12-25% in the nonsaponifiable fraction of soybean oil. The sterols are extracted as a mixture, but their similarity makes the purification and isolation of stigmasterol extremely difficult.|A plant sterol
Method: EPA-OW/OST 1698; Procedure: high resolution gas chromatography combined with high resolution mass spectrometry; Analyte: stigmasterol; Matrix: multi-media environmental samples; Detection Limit: 0.6 nanograms/L.
Computed Properties
Molecular Weight:412.7
XLogP3:8.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:5
Exact Mass:412.370516150
Monoisotopic Mass:412.370516150
Topological Polar Surface Area:20.2
Heavy Atom Count:30
Complexity:674
Undefined Atom Stereocenter Count:9
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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4 YRS
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STIGMASTEROL
4736-55-4
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Stigmasterol 3-O-β-D-glucopyranoside
19716-26-8
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Stigmasterol acetate
4651-48-3
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[2-[4-Methyl-2-(2-methyl-1-oxopropoxy)phenyl]-2-oxiranyl]methyl 2-methylbutanoate Formula
22518-07-6
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Xanthydrol Formula
90-46-0
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CAFFEIC ACID, 3-METHYL PHENETHYL ESTER Formula
71835-85-3
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Berberine Structure
2086-83-1
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Umbelliferone Structure
93-35-6
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What is Fumonisin B1
116355-83-0
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What is (-)-Loganin
18524-94-2
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