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Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
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| Food Chemicals Codex Listed: | No |
| Boiling Point: | 690.90 °C. @ 760.00 mm Hg (est)
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| Flash Point: | 448.00 °F. TCC ( 231.20 °C. ) (est)
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| logP (o/w): | -0.436 (est) |
| Soluble in: |
| | water, 1800 mg/L @ 25 °C (exp) | | | water, 6270 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
oral-mouse LD50 1200 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 114, Pg. 307, 1958.
oral-rat LD50 800 mg/kg
"CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 8(2), Pg. 172, 1982.
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| Dermal Toxicity: |
subcutaneous-mouse LD50 28 mg/kg
"CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 8(2), Pg. 172, 1982.
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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 glaucarubin usage levels up to: | | | not for fragrance use.
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| Recommendation for glaucarubin flavor usage levels up to: |
| | not for flavor use.
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Safety References:
References:
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| (1beta,2alpha,11beta,12alpha,15beta(S))-11,20- | epoxy-1,2,11,12-tetrahydroxy-15-(2-hydroxy-2-methyl-1-oxobutoxy) picras-3-en-16-one | | | glarubin | | | glaucarubina | | | glaumeba | | alpha- | kirondrin | | | MK-53 | | | simarubaceae |
Articles:
| PubMed:Glaucarubinone and gemcitabine synergistically reduce pancreatic cancer growth via down-regulation of P21-activated kinases. |
| PubMed:The phytochemical glaucarubinone promotes mitochondrial metabolism, reduces body fat, and extends lifespan of Caenorhabditis elegans. |
| PubMed:Cytotoxic activity of Brazilian Cerrado plants used in traditional medicine against cancer cell lines. |
| PubMed:Quassinoid inhibition of AP-1 function does not correlate with cytotoxicity or protein synthesis inhibition. |
| PubMed:Antiviral activity of simalikalactone D, a quassinoid from Quassia africana. |
| PubMed:Novel esters of glaucarubolone as inducers of terminal differentiation of promyelocytic HL-60 cells and inhibitors of 7,12-dimethylbenz[a]anthracene-induced preneoplastic lesion formation in mouse mammary organ culture. |
| PubMed:Aphrodisiac evaluation in non-copulator male rats after chronic administration of Eurycoma longifolia Jack. |
| PubMed:Insect antifeedant and growth regulating activities of quassinoids from Samadera indica. |
| PubMed:Total synthesis of (+)-quassin. |
| PubMed:Nematocidal activity of quassinoids against a species of Diplogastridae. |
| PubMed:Studies on the anxiolytic activity of Eurycoma longifolia Jack roots in mice. |
| PubMed:Quassinoids from the twigs and thorns of Castela polyandra. |
| PubMed:Anti-malarial activities of acylated bruceolide derivatives. |
| PubMed:In vitro anti-trichomonic activity of Castela texana. |
| PubMed:Anticancer activity of glaucarubinone analogues. |
| PubMed:Mode of action of the anticancer quassinoids--inhibition of the plasma membrane NADH oxidase. |
| PubMed:Antimalarial and cytotoxic potential of four quassinoids from Hannoa chlorantha and Hannoa klaineana, and their structure-activity relationships. |
| PubMed:Effect of the quassinoids glaucarubolone and simalikalactone D on growth of cells permanently infected with feline and human immunodeficiency viruses and on viral infections. |
| PubMed:Anti-tuberculosis activity of quassinoids. |
| PubMed:Synthesis of cytotoxic fluorinated quassinoids. |
| PubMed:[Weitz' aminium salt initiated electron transfer reactions and application to the synthesis of natural products]. |
| PubMed:Bruceine B, a potent inhibitor of leukocyte-endothelial cell adhesion. |
| PubMed:Inhibitory effects of quassinoid derivatives on Epstein-Barr virus early antigen activation. |
| PubMed:Quassinoids as inhibitors of Epstein-Barr virus early antigen activation. |
| PubMed:Antifertility activity of Quassia amara in male rats - in vivo study. |
| PubMed:Indonesian medicinal plants. XVII. Characterization of quassinoids from the stems of Quassia indica. |
| PubMed:Two new quassinoids, ailantinols A and B, and related compounds from Ailanthus altissima. |
| PubMed:Effect of 7-day daily replacement of culture medium containing Eurycoma longifolia Jack constituents on the Malaysian Plasmodium falciparum isolates. |
| PubMed:Bruceanols G and H cytotoxic quassinoids from Brucea antidysenterica. |
| PubMed:Bruceosides D, E, and F, three new cytotoxic quassinoid glucosides from Brucea javanica. |
| PubMed:Antifertility activity of Quassia amara: quassin inhibits the steroidogenesis in rat Leydig cells in vitro. |
| PubMed:In vitro antimalarial activity of quassinoids from Eurycoma longifolia against Malaysian chloroquine-resistant Plasmodium falciparum isolates. |
| PubMed:In vitro cytotoxicity of chaparrin from Castela texana. |
| PubMed:Effects of chaparrin, nordihydroguaiaretic acid and their structural analogues on Entamoeba histolytica cultures. |
| PubMed:Antimalarial activity of cedronin. |
| PubMed:Bruceanols D, E, and F three new cytotoxic quassinoids from Brucea antidysenterica. |
| PubMed:A new antimalarial quassinoid from Simaba guianensis. |
| PubMed:Quassinoids exhibit greater selectivity against Plasmodium falciparum than against Entamoeba histolytica, Giardia intestinalis or Toxoplasma gondii in vitro. |
| PubMed:Effect of quassin on the metabolism of catecholamines in different life cycle stages of Culex quinquefasciatus. |
| PubMed:Cytotoxic quassinoids from Cedronia granatensis. |
| PubMed:Mode of action of the antitumor compound girodazole (RP 49532A, NSC 627434). |
| PubMed:Antitumor agents, 127. Bruceoside C, a new cytotoxic quassinoid glucoside, and related compounds from Brucea javanica. |
| PubMed:Larvicidal efficacy of Quassin against Culex quinquefasciatus. |
| PubMed:Picrasinoside H, a new quassinoid glucoside, and related compounds from the stem wood of Picrasma ailanthoides. |
| PubMed:In vitro cytotoxicity of a series of quassinoids from Brucea javanica fruits against KB cells. |
| PubMed:Antitumor agents, 118. The isolation and characterization of bruceanic acid A, its methyl ester, and the new bruceanic acids B, C, and D, from Brucea antidysenterica. |
| PubMed:[Studies on pharmacologically active principles from Indonesian crude drugs. III. Toxic components from Brucea javanica (L.) Merr]. |
| PubMed:[Studies on the chemical constituents of Brucea javanica (L.) Merr]. |
| PubMed:Studies on the constituents of Indonesian Picrasma javanica. III. Structures of new quassinoids, javanicins A, C and D. |
| PubMed:Antitumor agents, 104. Isolation of yadanziosides M and P from Brucea antidysenterica and identification of bruceantinoside B as a mixture of yadanzioside P and bruceantinoside C. |
| PubMed:Use of microdilution to assess in vitro antiamoebic activities of Brucea javanica fruits, Simarouba amara stem, and a number of quassinoids. |
| PubMed:1H- and 13C-NMR spectroscopic studies of selected quassinoids. |
| PubMed:Antitumor activity of novel ailanthone derivatives in vitro and in vivo. |
| PubMed:Antitumor agents, 93. Bruceanol C, a new cytotoxic quassinoid from Brucea antidysenterica. |
| PubMed:Metabolism of plant-derived anticancer agents. |
| PubMed:Antitumor agents, 90. Bruceantinoside C, a new cytotoxic quassinoid glycoside from Brucea antidysenterica. |
| PubMed:Antimalarial agents, 4. Synthesis of a brusatol analog and biological activity of brusatol-related compounds. |
| PubMed:Acute insecticidal activity of quassin and its congeners against the American cockroach. |
| PubMed:Plants as sources of antimalarial drugs, Part 4: Activity of Brucea javanica fruits against chloroquine-resistant Plasmodium falciparum in vitro and against Plasmodium berghei in vivo. |
| PubMed:[Therapeutic trials of experimental murine malaria with the quassinoid, glaucarubinone]. |
| PubMed:Yadanzioside P, a new antileukemic quassinoid glycoside from Brucea javanica (L.) Merr with the 3-O-(beta-D-glucopyranosyl)bruceantin structure. |
| PubMed:Plants as sources of antimalarial drugs: in vitro antimalarial activities of some quassinoids. |
| PubMed:Two new quassinoids from Simaba multiflora fruits. |
| PubMed:[Castela texana: screening for its anti-amoebic activity]. |
| PubMed:Antitumor agents, 74. Bruceanol-A and -B, two new antileukemic quassinoids from Brucea antidysenterica. |
| PubMed:Growth inhibitory, insecticidal and antifeedant effects of some antileukemic and cytotoxic quassinoids on two species of agricultural pests. |
| PubMed:Quassinoid bitter principles. II. |
| PubMed:Evaluation of bleomycin, chlorozotocin, MGBG, and bruceantin in patients with advanced soft tissue sarcoma, bone sarcoma, or mesothelioma. |
| PubMed:Antitumor agents, 65. Brusatol and cleomiscosin-A, antileukemic principles from Brucea javanica. |
| PubMed:Reversibility of protein synthesis inhibition by quassinoid antineoplastic agents in a rabbit reticulocyte system. |
| PubMed:An enzyme-linked immunosorbent assay for quassin and closely related metabolites. |
| PubMed:Anti-inflammatory agents III: Structure-activity relationships of brusatol and related quassinoids. |
| PubMed:Antimalarial activity of bruceantin in vitro. |
| PubMed:Antitumor agents LIX: effects of quassinoids on protein synthesis of a number of murine tumors and normal cells. |
| PubMed:Structure-activity relationships for binding and inactivation of rabbit reticulocyte ribosomes by quassinoid antineoplastic agents. |
| PubMed:A Phase II study of Bruceantin (NSC-165, 563) in advanced malignant melanoma. |
| PubMed:Phase II trial of bruceantin in metastatic breast carcinoma. |
| PubMed:Bruceantin, a potent amoebicide from a plant, Brucea antidysenterica. |
| PubMed:Antitumor agents XLVIII: Structure-activity relationships of quassinoids as in vitro protein synthesis inhibitors of P-388 lymphocytic leukemia tumor cell metabolism. |
| PubMed:Antitumor agents XLVI: In vitro effects of esters of brusatol, bisbrusatol, and related compounds on nucleic acid and protein synthesis of P-388 lymphocytic leukemia cells. |
| PubMed:Antitumor agents XLV: Bisbrusatolyl and brusatolyl esters and related compounds as novel potent antileukemic agents. |
| PubMed:Antitumor agents XLVII: The effects of bisbrusatolyl malonate on P-388 lymphocytic leukemia cell metabolism. |
| PubMed:Clinical pharmacology of bruceantin by radioimmunoassay. |
| PubMed:[Mode of action of new antitumor compounds]. |
| PubMed:In vitro activity of certain quassinoid anti-tumor agents against Entamoeba histolytica. |
| PubMed:Antitumor agents XLII: Comparison of antileukemic activity of helenalin, brusatol, and bruceantin and their esters on different strains of P-388 lymphocytic leukemic cells. |
| PubMed:Phase I study on bruceantin administered on a weekly schedule. |
| PubMed:Mechanism of eukaryotic protein synthesis inhibition by brusatol. |
| PubMed:Antitumor agents. 39. Bruceantinoside-A and -B, novel antileukemic quassinoid glucosides from Brucea antidysenterica. |
| PubMed:Soularubinone, a new antileukemic quassionoid from Soulamea tomentosa. |
| PubMed:Antimalarial activity of quassinoids against chloroquine-resistant Plasmodium falciparum in vitro. |
| PubMed:Bruceolides from Filjian Brucea javanica. |
| PubMed:[Antiamebic properties of some derivatives of ailantone and quassin]. |
| PubMed:[The chemical constituents of the Chinese drug "Yadanzi." I. Isolation and identification of daucosterol, brucein D and brucein E (author's transl)]. |
| PubMed:Radioimmunoassay for the detection and quantitation of bruceantin. |
| PubMed:The antineoplastic quassinoids of Simaba cuspidata spruce and Ailanthus grandis Prain. |
| PubMed:Bruceantin, an inhibitor of the initiation of protein synthesis in eukaryotes [proceedings]. |
| PubMed:Structural requirements of quassinoids for the inhibition of cell transformation. |
| PubMed:Cytotoxic bruceolides from Brucea javanica [proceedings]. |
| PubMed:Phase I trial of bruceantin. |
| PubMed:Initial clinical studies with bruceantin. |
| PubMed:Antitumor agents. XXXIV: Mechanism of action of bruceoside A and brusatol on nucleic acid metabolism of P-388 lymphocytic leukemia cells. |
| PubMed:Antitumor agents. XXXV: Effects of brusatol, bruceoside A, and bruceantin on P-388 lymphocytic leukemia cell respiration. |
| PubMed:Disposition and metabolism of bruceantin in the mouse. |
| PubMed:Potential anticancer agents IX. Isolation of a new simaroubolide, 6alpha-tigloyloxychaparrinone, from Ailanthus integrifolia ssp. calycina (Simaroubaceae). |
| PubMed:Plant antitumor agents. XVI. 6alpha-Senecioyloxy-chaparrinone, a new antileukemic quassinoid from Simaba multiflora. |
| PubMed:New natural products of interest under development at the National Cancer Institute. |
| PubMed:Potential anticancer agents vi. Constituents of Ailanthus excelsa (Simaroubaceae). |
| PubMed:Antitumor plants. IV. Constituents of Simarouba versicolor. |
| PubMed:Structural requirements for biological activity among antileukemic glaucarubolone ester quassinoids. |
| PubMed:Treatment of amebic abscess of the liver. |
| PubMed:Effects of amebicides on growth of Acanthamoeba sp. |
| PubMed:CRYSTAL AND MOLECULAR STRUCTURE OF GLAUCARUBIN. |
| PubMed:[The treatment of intestinal amebiasis with glaucarubin. Apropos of 173 case]. |
| PubMed:[Treatment of autochthonous chronic non-dy-senteric amebiasis with glaucarubin]. |
| PubMed:[The treatment of intestinal amebiasis by glaucarubin]. |
| PubMed:Chemotherapeutic and pharmacological studies on glaucarubin, a specific amebacide. |
| PubMed:The use of glaucarubin (a crystalline glycoside isolated from Simarouba glauca) in the treatment of human colonic amebiasis. |
| PubMed:Symposium on the treatment of human amoebiasis. II. The treatment of intestinal amoebiasis with emetine bismuth iodide, glaucarubin, dichloroacet-hydroxy-methylanilide, camoform and various antibiotics. |
| PubMed:Clinical trial of glaucarubin in treatment of amebiasis. |
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(1 beta,2 alpha,11 beta,12 alpha,15 beta(s))-11,20-epoxy-1,2,11,12-tetrahydroxy-15-(2-hydroxy-2-methyl-1-oxobutoxy)picras-3-en-16-one. a quassinoid (simaroubolide) from simaruba glauca, a tropical shrub. it has been used as an antiamebic agent and is found to be cytotoxic. it may be of use in cancer chemotherapy. Isol. from Simarouba glauca (aceituno)
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3D/inchi