| Name: | (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 Number: | 474-67-9 |  3D/inchi
|
| ECHA EINECS - REACH Pre-Reg: | 207-486-5 |
| FDA UNII: | 2B0KG2XFOF |
| MDL: | MFCD00201659 |
| XlogP3-AA: | 8.00 (est) |
| Molecular Weight: | 398.67382000 |
| Formula: | C28 H46 O |
| NMR Predictor: | Predict (works with chrome, Edge or firefox) |
Category:food additive, phytosterols
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
| |
| Hazards identification |
| |
| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
| |
| Pictogram | |
| |
| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
|
Not determined
|
| Dermal Toxicity: |
|
Not determined
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| Inhalation Toxicity: |
|
Not determined
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Safety in Use Information:
| Category: | | food additive, phytosterols |
| Recommendation for brassicasterol usage levels up to: | | | not for fragrance use.
|
| |
| Recommendation for brassicasterol flavor usage levels up to: |
| | not for flavor use.
|
Safety References:
European Food Safety Authority (EFSA) reference(s):
|
Scientific Opinion on the safety of stigmasterol-rich plant sterols as food additive
View page or View pdf
|
| EPI System: View |
| ClinicalTrials.gov:search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :6432458 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| (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 |
| Chemidplus:0000474679 |
References:
| | (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 |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 474-67-9 |
| Pubchem (cid): | 6432458 |
| Pubchem (sid): | 134973141 |
| Pherobase: | View |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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 |
Articles:
| 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. |
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