| Name: | (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(E,2R)-5-propan-2-ylhept-5-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol |
| CAS Number: | 17605-67-3 |  3D/inchi
|
| FDA UNII: | 504ZAM710C |
| Nikkaji Web: | J9.102B |
| MDL: | MFCD00037543 |
| XlogP3-AA: | 8.90 (est) |
| Molecular Weight: | 412.70076000 |
| Formula: | C29 H48 O |
| BioActivity Summary: | listing |
| NMR Predictor: | Predict (works with chrome, Edge or firefox) |
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
|
| Food Chemicals Codex Listed: | No |
| Boiling Point: | 504.20 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 429.00 °F. TCC ( 220.30 °C. ) (est)
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| logP (o/w): | 10.410 (est) |
| Soluble in: |
| | water, 5.639e-005 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 | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
|
Not determined
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| Dermal Toxicity: |
|
Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for fucosterol usage levels up to: | | | not for fragrance use.
|
| |
| Recommendation for fucosterol flavor usage levels up to: |
| | not for flavor use.
|
Safety References:
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :5281328 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(E,2R)-5-propan-2-ylhept-5-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol |
| Chemidplus:0017605673 |
References:
| | (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(E,2R)-5-propan-2-ylhept-5-en-2-yl]-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: | 17605-67-3 |
| Pubchem (cid): | 5281328 |
| Pubchem (sid): | 135073699 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| (3S,8S,9S,10R,13R,14S,17R)-10,13- | dimethyl-17-[(E,2R)-5-propan-2-ylhept-5-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol | | 24- | ethylidenecholest-5-en-3b-ol | | 24-iso | ethylidenecholest-5-en-3beta-ol, delta(5)-avenasterol | | 28-iso | fucosterol | | (24E)-24-N- | propylidenecholesterol | | | stigmasta-5,24-dien-3beta-ol | | | stigmasta-5,24(28)-dien-3-ol, (3beta,24E)- |
Articles:
| PubMed:Thresholds for Sterol-Limited Growth of Daphnia magna: A Comparative Approach Using 10 Different Sterols. |
| PubMed:24(S)-saringosterol from edible marine seaweed Sargassum fusiforme is a novel selective LXRβ agonist. |
| PubMed:In vitro and in silico studies on the anticancer and apoptosis-inducing activities of the sterols identified from the soft coral, subergorgia reticulata. |
| PubMed:Cytotoxic and antiproliferative constituents from Dictyota ciliolata, Padina sanctae-crucis and Turbinaria tricostata. |
| PubMed:Seasonal changes in lipid, fatty acid, α-tocopherol and phytosterol contents of seaweed, Undaria pinnatifida, in the Marlborough Sounds, New Zealand. |
| PubMed:Extraction optimization by response surface methodology: Purification and characterization of phytosterol from sugarcane (Saccharum officinarum L.) rind. |
| PubMed:The bone regenerative effects of fucosterol in in vitro and in vivo models of postmenopausal osteoporosis. |
| PubMed:Characterization of oilseed lipids from "DHA-producing Camelina sativa": a new transformed land plant containing long-chain omega-3 oils. |
| PubMed:Biological activity and chemical constituents of red and brown algae from the persian gulf. |
| PubMed:Study on human promyelocytic leukemia HL-60 cells apoptosis induced by fucosterol. |
| PubMed:The protective effects of fucosterol against skin damage in UVB-irradiated human dermal fibroblasts. |
| PubMed:Anti-adipogenic activity of the edible brown alga Ecklonia stolonifera and its constituent fucosterol in 3T3-L1 adipocytes. |
| PubMed:Kinetics and molecular docking studies of an anti-diabetic complication inhibitor fucosterol from edible brown algae Eisenia bicyclis and Ecklonia stolonifera. |
| PubMed:Pachydictyols B and C: new diterpenes from Dictyota dichotoma Hudson. |
| PubMed:Developmental changes in the sterol composition and the glycerol content of cuticular and internal lipids of three species of flies. |
| PubMed:Anti-inflammatory activity of edible brown alga Eisenia bicyclis and its constituents fucosterol and phlorotannins in LPS-stimulated RAW264.7 macrophages. |
| PubMed:Anti-hyperglycaemic activity of swietenia macrophylla king (meliaceae) seed extracts in normoglycaemic rats undergoing glucose tolerance tests. |
| PubMed:Composition of Cassia fistula oil and its antifungal activity by disrupting ergosterol biosynthesis. |
| PubMed:Fucosterol inhibits matrix metalloproteinase expression and promotes type-1 procollagen production in UVB-induced HaCaT cells. |
| PubMed:Valuable compounds in macroalgae extracts. |
| PubMed:Fucosterol is a selective liver X receptor modulator that regulates the expression of key genes in cholesterol homeostasis in macrophages, hepatocytes, and intestinal cells. |
| PubMed:Phytochemical and biological studies on some Egyptian seaweeds. |
| PubMed:Fucosterol isolated from Undaria pinnatifida inhibits lipopolysaccharide-induced production of nitric oxide and pro-inflammatory cytokines via the inactivation of nuclear factor-κB and p38 mitogen-activated protein kinase in RAW264.7 macrophages. |
| PubMed:Gracilariopsis persica from Persian Gulf Contains Bioactive Sterols. |
| PubMed:Cytotoxicity of fucosterol containing fraction of marine algae against breast and colon carcinoma cell line. |
| PubMed:Isolation of phytosterols and antihyperlipidemic activity of Lagenaria siceraria. |
| PubMed:Antioxidant, cytotoxic, antitumor, and protective DNA damage metabolites from the red sea brown alga Sargassum sp. |
| PubMed:Sterols from Sargassum oligocystum, a brown algae from the Persian Gulf, and their bioactivity. |
| PubMed:Glycolipid composition of Hevea brasiliensis latex. |
| PubMed:New antifungal steroids from Turbinaria conoides (J. Agardh) Kutzing. |
| PubMed:Sterol biosynthesis in oomycete pathogens. |
| PubMed:[Studies on chemical constituents of fructus broussonetiae]. |
| PubMed:Sterol metabolism in the oomycete Aphanomyces euteiches, a legume root pathogen. |
| PubMed:Screening for bioactive compounds from algae. |
| PubMed:Chemical components and its antioxidant properties in vitro: an edible marine brown alga, Ecklonia cava. |
| PubMed:Determination of total sterols in brown algae by Fourier transform infrared spectroscopy. |
| PubMed:Effects of plant sterols on human multidrug transporters ABCB1 and ABCC1. |
| PubMed:Bioassay-guided fractionation of antifertility components of castorbean (Ricinus communis L.) seed extracts. |
| PubMed:Cytotoxic sterols from the formosan brown alga Turbinaria ornata. |
| PubMed:Inhibitory activity on HIV-1 reverse transcriptase and integrase of a carmalol derivative from a brown Alga, Ishige okamurae. |
| PubMed:[Studies on chemical constituents of the brown alga Dictyopteris divaricata]. |
| PubMed:[Studies on the chemical constituents of the alga Sargassum carpophyllum J. Agardh]. |
| PubMed:Anti-diabetic activities of fucosterol from Pelvetia siliquosa. |
| PubMed:Biosynthesis of the irregular monoterpene artemisia ketone, the sesquiterpene germacrene D and other isoprenoids in Tanacetum vulgare L. (Asteraceae). |
| PubMed:An HPLC method for the quantification of sterols in edible seaweeds. |
| PubMed:Anti-oxidant activities of fucosterol from the marine algae Pelvetia siliquosa. |
| PubMed:Fatty acids bound to Fasciola hepatica 12 kDa fatty acid-binding protein, a candidate vaccine, differ from fatty acids in extracts of adult flukes. |
| PubMed:Cytotoxic hydroazulene diterpenes from the brown alga Dictyota dichotoma. |
| PubMed:Sterol C-24 methyltransferase type 1 controls the flux of carbon into sterol biosynthesis in tobacco seed. |
| PubMed:Bioactive steroids from the brown alga Sargassum carpophyllum. |
| PubMed:Inhibition of Mycobacterium tuberculosis growth by saringosterol from Lessonia nigrescens. |
| PubMed:Site-Directed Mutagenesis of the Sterol Methyl Transferase Active Site from Saccharomyces cerevisiae Results in Formation of Novel 24-Ethyl Sterols. |
| PubMed:[Residual chemicals in natural rubber products for food contact use]. |
| PubMed:New cytotoxic oxygenated fucosterols from the brown alga Turbinaria conoides. |
| PubMed:Acid-catalyzed isomerization of fucosterol and delta5-avenasterol. |
| PubMed:The Arabidopsis DIMINUTO/DWARF1 gene encodes a protein involved in steroid synthesis. |
| PubMed:Sterol utilization and metabolism by Heliothis zea. |
| PubMed:A succinylanthranilic acid ester and other bioactive constituents of Jolyna laminarioides. |
| PubMed:Side-chain structure is critical for the transport of sterols from lysosomes to cytoplasm. |
| PubMed:Comparative study on inclusion complexation of maltosyl-beta-cyclodextrin, heptakis(2,6-di-O-methyl)-beta-cyclodextrin and beta-cyclodextrin with fucosterol in aqueous and solid state. |
| PubMed:Dual specificity of sterol-mediated glycoalkaloid induced membrane disruption. |
| PubMed:Phospholipid studies of marine organisms: 26. Interactions of some marine sterols with 1-stearoyl-2-oleoyl phosphatidylcholine (SOPC) in model membranes. |
| PubMed:[Sterols from Gynostemma pentafillum]. |
| PubMed:Intermediates of stigmasterol metabolism in Spodoptera littoralis. |
| PubMed:Inhibition of cholesterol absorption in rats by plant sterols. |
| PubMed:Visible fibrinolysis by endothelial cells: effect of vitamins and sterols. |
| PubMed:Fucosterol decreases angiotensin converting enzyme levels with reduction of glucocorticoid receptors in endothelial cells. |
| PubMed:Fucosterol epoxide lyase of insects: synthesis of labeled substrates and development of a partition assay. |
| PubMed:Sterols from Equisetum arvense. |
| PubMed:Successive study on the production of plasminogen activator in cultured endothelial cells by phytosterol. |
| PubMed:Sterol metabolism in the nematodeCaenorhabditis elegans. |
| PubMed:Comparative effects of growth inhibitors on sterol metabolism in the nematode Caenorhabditis elegans. |
| PubMed:Evidence for metabolic and functional discrimination of sterols by Phytophthora cactorum. |
| PubMed:Comparative lymphatic absorption of sitosterol, stigmasterol, and fucosterol and differential inhibition of cholesterol absorption. |
| PubMed:Cycloartenol-derived sterol biosynthesis in the Peronosporales. |
| PubMed:[Biologically active sterols--stereochemistry of sterol side chain and their biological significance]. |
| PubMed:Metabolism of sterols by anaerobic Saccharomyces cerevisiae. |
| PubMed:Stereochemical importance of fucosterol epoxide in the conversion of sitosterol into cholesterol in the silkworm Bombyx mori. |
| PubMed:Isolation of two new C30 sterols, (24E)-24-N-propylidenecholesterol and 24 epsilon-N-propylcholesterol, from a cultured marine Chrysophyte. |
| PubMed:Metabolism in porifera. VII. Conversion of [7,7-3H2]-fucosterol into calysterol by the sponge Calyx niceaensis. |
| PubMed:[Fucosterol-24,28-epoxide, an intermediate in the oxidative biodegredation of fucosterol to cholesterol by the cricket (Locusta migratoria (R. and F.)]. |
| PubMed:[Study fo sterols from brown seaweeds of the genus Cytoseira. Identification by gas-liquid chromatography coupled with mass spectrometry (author's transl)]. |
| PubMed:Preparation of fucosterol from giant kelp. |
| PubMed:Letter: Stereospecificity in the conversion of fucosterol 24,28-epoxide to desmosterol in the silkworm, Bombyx mori. |
| PubMed:Carbon-carbon bond cleavage of fucosterol-24, 28-oxide by cell-free extracts of silkworm Bombyx mori. |
| PubMed:Studies on steroids. Part XXIX. Synthesis of allenic analogues fucosterol and desmosterol. |
| PubMed:Production of hormone B by Achlya heterosexualis. |
| PubMed:Identification of fucosterol as a metabllite and probable intermediate in conversion of beta-sitosterol to cholesterol in the tobacco hornworm. |
| PubMed:[Determination of fucosterol in Fucus vesiculosus L. and in extracts of Fucus vesiculosus L]. |
| PubMed:Studies in phytosterol biosynthesis: observations on the biosynthesis of fucosterol in the marine brown alga Fucus spiralis. |
| PubMed:Fucosterol Reduction to Clionasterol in vivo by Chlorella ellipsoidea. |
| PubMed:Confirmation of the structure of fucosterol by nuclear magnetic resonan spectroscopy (1). |
| PubMed:The biosynthesis of sterols in higher plants. |
| PubMed:Steroid studies. VII. Syntheses of sargasterol, fucosterol, and C 20-isocholesterol. |
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