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isatidine

isatidine Structure
isatidine
  • CAS No.15503-86-3
  • Chemical Name:isatidine
  • CBNumber:CB31306005
  • Molecular Formula:C18H25NO7
  • Formula Weight:367.39
  • MOL File:15503-86-3.mol
isatidine Property
  • Melting point 145°C
  • Boiling point 497.95°C (rough estimate)
  • Density 1.3204 (rough estimate)
  • refractive index 1.5100 (estimate)
  • pka 11.96±0.40(Predicted)
  • FDA UNII 51819GRV4U
  • IARC 3 (Vol. 10, Sup 7) 1987
  • EPA Substance Registry System Isatidine (15503-86-3)
Safety
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordDanger
  • Hazard statements H373-H300
  • Precautionary statements P260-P314-P501-P264-P270-P301+P310-P321-P330-P405-P501

isatidine Chemical Properties,Usage,Production

  • Description This hepatotoxic alkaloid occurs in certain Senecio species and was first isolated from S. isatideus D.C. It occurs abundantly in S. retrorsus D.C. and S. scleratus Schw. The alkaloid crystallizes in rhombic prisms as the dihydrate and has [α]27D . 8.25° (H 20). It is soluble in MeOH, hot EtOH and hot H20 but virtually insoluble in Et 20, Me2CO or CHCl 3. On reduction it absorbs 4 molecules of H2 to give hexahydrodeoxyisatidine which melts at l15-l20°C and then remelts at l83-4°C following an intermediate solidification. This compound gives a hydrochloride, m.p. 218°C (dec.); [α]20D - 52.5° (H20) and may be hydrolyzed with Ba(OHh to give a basic product, tetrahydroisatinecine, CSH1703N, m.p. l74.5°C; [α]20D - 88° (H 20). The alkaloid itself, on hydrolysis with Ba(OHh yields isatinecine and two acid products, isatinecic acid and the monolactone, the latter almost certainly being formed by the action of the base upon the acid.
  • Uses Retrorsine N-oxide-D4 is a labelled analogue of Retrorsine N-oxide (R279005). Retrorsine N-oxide is a pyrrolizidine alkaloid that is naturally found in Senecio isatideus, a flowering plant that is native to the Netherlands. Retrorsine N-oxide is also known to raise blood pressure and can induce abnormal changes in the liver if ingested by animals or humans.
  • Definition ChEBI: Isatidine is a citraconoyl group.
  • Safety Profile Poison by ingestion and intraperitoneal routes. Moderately toxic by intravenous route. Questionable carcinogen with experimental neoplastigenic and tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NO,. See also ESTERS.
  • in vivo

    Retrorsine N-oxide produces DNA adducts, the common biological biomarker of PA-induced liver tumor formation[1].

  • References Blackie., Pharrn. J., 138, 102 (1937) de Waal., Onderstepoort J., 12, 155 (1939) de Waal., Nature, 146, 777 (1940) de Waal., Pretorius., OnderstepoortJ., 17,181 (1941) Leisegang, Warren., J. Chern. Soc., 702 (1950)
isatidine Preparation Products And Raw materials
Raw materials
Preparation Products
isatidine Suppliers
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isatidine Spectrum
15503-86-3, isatidineRelated Search:
  • 标准品
  • 15505-86-3
  • 化合物 T32198
  • 靛红定
  • 菘蓝千里光碱
  • 倒千里光碱N-氧化物
  • 15503-86-3
  • [1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-, 12-oxide, (3Z,5R,6S,14aR,14bR)-
  • Retrorsin-N-oxid
  • 12,18-Dihydroxysenecionane-11,16-dione 4-oxide
  • 12,18-Dihydroxy-11,16-dioxosenecionane 4-oxide
  • RETRORSINE-N-OXIDE
  • isatidine

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