fucosterol

24-ethylidenecholest-5-en-3b-ol

CAS: 17605-67-3 C29 H48 O MW: 412.70076000

Identification

Namefucosterol
IUPAC(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 Number17605-67-3
FDA UNII504ZAM710C
Molecular FormulaC29 H48 O
Molecular Weight412.70076000
MDL NumberMFCD00037543
Nikkaji NumberJ9.102B

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 504.20 °C. @ 760.00 mm Hg (est)
Flash Point 429.00 °F. TCC ( 220.30 °C. ) (est)
logP (o/w) 10.410 (est)
Soluble in water, 5.639e-005 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

Categorynatural substances and extractives
Recommendation for fucosterol usage levels up tonot for fragrance use.
Recommendation for fucosterol flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

bladderwrack coconut pollen lemongrass plant

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)- 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.