brassicasterol

ergosta-5,22(E)-dien-3beta-ol

CAS: 474-67-9 C28 H46 O MW: 398.67382000

Identification

Namebrassicasterol
IUPAC(3S)-17-[(E)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
CAS Number474-67-9
EINECS207-486-5
FDA UNII2B0KG2XFOF
Molecular FormulaC28 H46 O
Molecular Weight398.67382000
MDL NumberMFCD00201659

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 488.00 to 489.00 °C. @ 760.00 mm Hg (est)
Flash Point 416.00 °F. TCC ( 213.30 °C. ) (est)
logP (o/w) 9.679 (est)
Soluble in water, 0.0002336 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryfood additive, phytosterols
Recommendation for brassicasterol usage levels up tonot for fragrance use.
Recommendation for brassicasterol flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

brassica campestris ceratophyllum demersum cystoseira barbata date palm seed marango seed marchantia convoluta mustard field mustard nereis succinea oat seed onion seed rape schleichera trijuga leaf sunflower pollen tea seed oil walnut english walnut nut

Synonyms

(3S)-17-[(E)-5,6- dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol (3beta,22E)- ergosta-5,22-dien-3-ol ergosta-5,22-dien-3-ol, (3.beta.,22E)- ergosta-5,22-dien-3-ol, (3beta,22E)- ergosta-5,22(E)-dien-3beta-ol PubMed: Spatial distributions of methoxylated and hydroxylated polybrominated diphenyl ethers in the East China Sea-A seaward increasing trend. PubMed: Determination of sterols using liquid chromatography with off-line surface-assisted laser desorption/ionization mass spectrometry. PubMed: Major sources of MeO/OH-BDEs in the East China Sea elucidated from their records and phytoplankton biomarkers. PubMed: Dragmacidoside: a new nucleoside from the Red Sea sponge Dragmacidon coccinea. PubMed: A comparative calorimetric study of the effects of cholesterol and the plant sterols campesterol and brassicasterol on the thermotropic phase behavior of dipalmitoylphosphatidylcholine bilayer membranes. PubMed: Characterization of oilseed lipids from "DHA-producing Camelina sativa": a new transformed land plant containing long-chain omega-3 oils. PubMed: Anti-Inflammatory Effects and Mechanisms of Fatsia polycarpa Hayata and Its Constituents. PubMed: Method development for forensic identification of biodiesel based on chemical fingerprints and corresponding diagnostic ratios. PubMed: Degradation of phytosterols during storage of enriched margarines. PubMed: Health applications of bioactive compounds from marine microalgae. PubMed: Quantitative analysis of phytosterols in edible oils using APCI liquid chromatography-tandem mass spectrometry. PubMed: Composition and sources of aliphatic lipids and sterols in sediments of a tropical island, southern South China Sea: preliminary assessment. PubMed: Characterization of cell wall lipids from the pathogenic phase of Paracoccidioides brasiliensis cultivated in the presence or absence of human plasma. PubMed: Effects of environmental factors on edible oil quality of organically grown Camelina sativa. PubMed: Sugar availability modulates polyisoprenoid and phytosterol profiles in Arabidopsis thaliana hairy root culture. PubMed: New secondary metabolites from bioactive extracts of the fungus Armillaria tabescens. PubMed: Sterol composition of shellfish species commonly consumed in the United States. PubMed: The Effect of Temperature and Moisture Content of Stored Rapeseed on the Phytosterol Degradation Rate. PubMed: Lipidomic analysis of extracellular vesicles from the pathogenic phase of Paracoccidioides brasiliensis. PubMed: Sterol lipid metabolism in down syndrome revisited: down syndrome is associated with a selective reduction in serum brassicasterol levels. PubMed: Antiprotozoal and antimicrobial compounds from the plant pathogen Septoria pistaciarum. PubMed: Investigation of unsaponifiable matter of plant oils and isolation of eight phytosterols by means of high-speed counter-current chromatography. PubMed: An ultra performance liquid chromatographic method for determining phytosterol uptake by Caco-2 cells. PubMed: Mode of action of membrane-disruptive lytic compounds from the marine dinoflagellate Alexandrium tamarense. PubMed: Vitamin D and sterol composition of 10 types of mushrooms from retail suppliers in the United States. PubMed: The plant sterol brassicasterol as additional CSF biomarker in Alzheimer's disease. PubMed: The search of new biomarkers to identify Alzheimer's disease: an editorial comment to T. Vanmierlo et al. 'The plant sterol brassicasterol and additional CFS biomarker in Alzheimer's Disease' (1). PubMed: Soyasapogenol B and trans-22-dehydrocam- pesterol from common vetch (Vicia sativa L.) root exudates stimulate broomrape seed germination. PubMed: Chemical composition and bioactivities of the marine alga Isochrysis galbana from Taiwan. PubMed: Determination of polar impurities in biodiesels using solid-phase extraction and gas chromatography-mass spectrometry. PubMed: Cloning, mechanistic and functional analysis of a fungal sterol C24-methyltransferase implicated in brassicasterol biosynthesis. PubMed: Genetic regulation of serum phytosterol levels and risk of coronary artery disease. PubMed: Phylogenetic distribution of fungal sterols. PubMed: Competitive solubilization of cholesterol and six species of sterol/stanol in bile salt micelles. PubMed: Dietary phytosterols and phytostanols alter the expression of sterol-regulatory genes in SHRSP and WKY inbred rats. PubMed: Effect of rapeseed oil-derived plant sterol and stanol esters on atherosclerosis parameters in cholesterol-challenged heterozygous Watanabe heritable hyperlipidaemic rabbits. PubMed: Plant sterols from rapeseed and tall oils: effects on lipids, fat-soluble vitamins and plant sterol concentrations. PubMed: Phytosterols accumulation in the seeds of Linum usitatissimum L. PubMed: Analysis of phytosterols in extra-virgin olive oil by nano-liquid chromatography. PubMed: Inhibition of cholesterol transport into skin cells in cultures by phytosterol-loaded microemulsion. PubMed: Development of liquid chromatographic methods for the determination of phytosterols in Standard Reference Materials containing saw palmetto. PubMed: Overexpression of CYP710A1 and CYP710A4 in transgenic Arabidopsis plants increases the level of stigmasterol at the expense of sitosterol. PubMed: Sterol composition in muscle and viscera of the marine bivalve Megangulus zyonoensis from coastal waters of Hokkaido, northern Japan. PubMed: Seasonal variations of lipid content and composition in Perna viridis. PubMed: Lymphatic absorption and deposition of various plant sterols in stroke-prone spontaneously hypertensive rats, a strain having a mutation in ATP binding cassette transporter G5. PubMed: Free radical oxidation (autoxidation) of alkenones and other lipids in cells of Emiliania huxleyi. PubMed: [Study on the sterols from a brown alga endophytic fungus (NO. ZZF36) from the South China Sea]. PubMed: Moderately elevated plant sterol levels are associated with reduced cardiovascular risk--the LASA study. PubMed: Cytochrome P450 subfamily CYP710A genes encode sterol C-22 desaturase in plants. PubMed: Solubility in and affinity for the bile salt micelle of plant sterols are important determinants of their intestinal absorption in rats. PubMed: Preliminary study on health-related lipid components of bakery products. PubMed: Nystatin-induced lipid vesicles permeabilization is strongly dependent on sterol structure. PubMed: Cytochrome P450 CYP710A encodes the sterol C-22 desaturase in Arabidopsis and tomato. PubMed: Ganoderma total sterol (GS) and GS1 protect rat cerebral cortical neurons from hypoxia/reoxygenation injury. PubMed: Effect of high plant sterol-enriched diet and cholesterol absorption inhibitor, SCH 58235, on plant sterol absorption and plasma concentrations in hypercholesterolemic wild-type Kyoto rats. PubMed: Rapid quantification of free and esterified phytosterols in human serum using APPI-LC-MS/MS. PubMed: Lipid [corrected] classes, fatty acids, and sterols in seafood from Gilbert Bay, southern labrador. PubMed: Contribution of lipoxygenase metabolism to the brassinosteroid signaling pathway. PubMed: Gas chromatographic separation and mass spectrometric identification of mixtures of oxyphytosterol and oxycholesterol derivatives application to a phytosterol-enriched food. PubMed: Long-chain alkenones and related compounds in the benthic haptophyte Chrysotila lamellosa Anand HAP 17. PubMed: Characterization of field-isolates and derived DMI-resistant strains of Cercospora beticola. PubMed: Formation of modified fatty acids and oxyphytosterols during refining of low erucic acid rapeseed oil. PubMed: Induction of intestinal ATP-binding cassette transporters by a phytosterol-derived liver X receptor agonist. PubMed: Fatty acid and sterol composition of frozen and freeze-dried New Zealand Green Lipped Mussel (Perna canaliculus) from three sites in New Zealand. PubMed: Sterol composition of gonad, muscle and digestive gland of Pecten maximus from Málaga (South Spain). PubMed: Expression of a Streptomyces 3-hydroxysteroid oxidase gene in oilseeds for converting phytosterols to phytostanols. PubMed: Inhibition of cholesterol biosynthesis by Delta22-unsaturated phytosterols via competitive inhibition of sterol Delta24-reductase in mammalian cells. PubMed: Lipid, FA, and sterol composition of New Zealand green lipped mussel (Perna canaliculus) and Tasmanian blue mussel (Mytilus edulis). PubMed: Interannual and between species comparison of the lipids, fatty acids and sterols of Antarctic krill from the US AMLR Elephant Island survey area. PubMed: Definitive structural identities of 42 sterol components in Pneumocystis carinii. PubMed: Tracing sewage in the marine environment: altered signatures in Concepción Bay, Chile. PubMed: Dietary cholesterol absorption; more than just bile. PubMed: Interannual variations in the lipids of the Antarctic pteropods Clione limacina and Clio pyramidata. PubMed: Plants steroid hormones, brassinosteroids: current highlights of molecular aspects on their synthesis/metabolism, transport, perception and response. PubMed: Marine lipids: overview "news insights and lipid composition of Lyprinol". PubMed: Fetal demise with Smith-Lemli-Opitz syndrome confirmed by tissue sterol analysis and the absence of measurable 7-dehydrocholesterol Delta(7)-reductase activity in chorionic villi. PubMed: CO2 as main carbon source for isoprenoid biosynthesis via the mevalonate-independent methylerythritol 4-phosphate route in the marine diatoms Phaeodactylum tricornutum and Nitzschia ovalis. PubMed: Mass spectrometry characterization of the 5alpha-, 7alpha-, and 7beta-hydroxy derivatives of beta-sitosterol, campesterol, stigmasterol, and brassicasterol. PubMed: Topical antiinflammatory activity of phytosterols isolated from Eryngium foetidum on chronic and acute inflammation models. PubMed: Regulation of rat hepatic 3beta-hydroxysterol delta7-reductase: substrate specificity, competitive and non-competitive inhibition, and phosphorylation/dephosphorylation. PubMed: Accurate detection of Smith-Lemli-Opitz syndrome carriers by measurement of the rate of reduction of the ergosterol C-7 double bond in cultured skin fibroblasts. PubMed: Nasal insulin delivery in rabbits using soybean-derived sterylglucoside and sterol mixtures as novel enhancers in suspension dosage forms. PubMed: Measurement of 3 beta-hydroxysteroid delta 7-reductase activity in cultured skin fibroblasts utilizing ergosterol as a substrate: a new method for the diagnosis of the Smith-Lemli-Opitz syndrome. PubMed: Identification and quantification of Tuber melanosporum Vitt. sterols. PubMed: Toxic oil syndrome: traceback of the toxic oil and evidence for a point source epidemic. PubMed: Comparative studies of metabolism of 4-desmethyl, 4-monomethyl and 4,4-dimethyl sterols in Manduca sexta. PubMed: The lipids of slugs and snails: evolution, diet and biosynthesis. PubMed: Sex pheromones in marine polychaetes: steroids from ripe Nereis succinea. PubMed: Metabolism of orally administered ergosterol and 7-dehydrocholesterol in rats and lack of evidence for their vitamin D biological activity. PubMed: Phycochemical studies on Scinaia fascicularis (Bonnemaisoniales, Rhodophyta). PubMed: Shellfish: proximate composition, minerals, fatty acids, and sterols. PubMed: Sterols of fungi responsible for superficial skin and nail infection. PubMed: Abnormal metabolism of shellfish sterols in a patient with sitosterolemia and xanthomatosis. PubMed: Physiological requirement for biosynthesis of multiple 24 beta-methyl sterols in Gibberella fujikuroi. PubMed: [Chemical composition and biological properties of Erythraea centaurium Rafn]. PubMed: Sterol composition of normal human bile. Effects of feeding shellfish (marine) sterols. PubMed: Chemical composition and anti-inflammatory activity of an alcoholic extract of Teucrium polium L. PubMed: Influence of processing on sterols of edible vegetable oils. PubMed: Anatomical distribution of sterols in oysters (Crassostrea gigas). PubMed: The effect of shellfish in the diet upon the plasma lipid levels in humans. PubMed: Further investigations of mutagenic cholesterol preparations. PubMed: Distribution of carotenoids and sterols in relation to the taxonomy of Taphrina and Protomyces. PubMed: Synthesis and biological activity of brassinolide and its 22 beta, 23 beta-isomer: novel plant growth-promoting steroids. PubMed: Absorption and transport of shellfish sterols in human subjects. PubMed: Lymphatic absorption of shellfish sterols and their effects on cholesterol absorption. PubMed: Marine sterols. VIII. Isolation and structure of sarcosterol, a new sterol with a delta17(20)-double bond from the soft coral Sarcophyton glaucum. PubMed: Chemical constituents of Vietnamese toad venom collected from Bufo melanostictus Schneider. Part I. The sterols. PubMed: [Role of sterol structure in complex formation with polyene antibiotics]. PubMed: [Study fo sterols from brown seaweeds of the genus Cytoseira. Identification by gas-liquid chromatography coupled with mass spectrometry (author's transl)]. PubMed: Metabolism of 2,4-3H-14alpha-methyl-5alpha-ergost-8-enol and 2,4-3H-5alpha-ergosta-8,14-dienol in Ochromonas malhamensis. PubMed: BRASSICASTEROL AND 22,23-DIHYDROBRASSICASTEROL FROM ERGOSTEROL VIA I-ERGOSTEROL.