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Santonin information


Santonin
Names
IUPAC name
(11S)-6α,12-Epoxyeudesma-1,4-diene-3,12-dione
Systematic IUPAC name
(3S,3aS,5aS,9bS)-3,5a,9-Trimethyl-3a,5,5a,9b-tetrahydronaphtho[1,2-b]furan-2,8(3H,4H)-dione
Identifiers
CAS Number
  • 481-06-1 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16363 ☒N
ChEMBL
  • ChEMBL259254 ☒N
ChemSpider
  • 191779 ☒N
ECHA InfoCard 100.006.874 Edit this at Wikidata
KEGG
  • D00154
  • C02206
PubChem CID
  • 221071
UNII
  • 1VL8J38ERO checkY
CompTox Dashboard (EPA)
  • DTXSID7045312 Edit this at Wikidata
InChI
  • InChI=1S/C15H18O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-8,10,13H,4,6H2,1-3H3/t8-,10-,13-,15-/m0/s1 ☒N
    Key: XJHDMGJURBVLLE-BOCCBSBMSA-N ☒N
SMILES
  • C[C@H]1[C@@H]2CC[C@]3(C=CC(=O)C(=C3[C@H]2OC1=O)C)C
Properties
Chemical formula
C15H18O3
Molar mass 246.30162
Melting point 172 °C (342 °F; 445 K)
Boiling point 423 °C (793 °F; 696 K)
Solubility in water
insoluble
Vapor pressure 1*10−7mmHg
Hazards
Flash point 190 °C (374 °F; 463 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Santonin is a drug which was widely used in the past as an anthelminthic. It is an organic compound consisting of colorless flat prisms, turning slightly yellow from the action of light and soluble in alcohol, chloroform and boiling water.

According to the US Pharmacopoeia, santonin occurs "in colorless, shining, flattened, prismatic crystals, odorless and nearly tasteless when first put in the mouth, but afterward developing a bitter taste; not altered by exposure to air, but turning yellow on exposure to light. Nearly insoluble in cold water; soluble in 40 parts of alcohol at 15 °C. (59 °F.), in 250 parts of boiling water, and in 8 parts of boiling alcohol; also soluble in 140 parts of ether, in 4 parts of chloroform, and in solutions of caustic alkalies. When heated to 170 °C. (338 °F.), santonin melts, and forms, if rapidly cooled, an amorphous mass, which instantly crystallizes oil coming in contact with a minute quantity of one of its solvents. At a higher temperature, it sublimes partly unchanged, and, when ignited, it is consumed, leaving no residue. Santonin is neutral to litmus paper moistened with alcohol. Santonin yields, with an alcoholic solution of potassium hydroxide, a bright pinkish-red liquid, which gradually becomes colorless. From its solution in caustic alkalies, santonin is completely precipitated by supersaturation with an acid".[1]

  1. ^ original source, US Pharmacopoeia, 1898

and 23 Related for: Santonin information

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Santonin

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Santonin is a drug which was widely used in the past as an anthelminthic. It is an organic compound consisting of colorless flat prisms, turning slightly...

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Organic photochemistry

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sunlights. The first reported case was by Ciamician that sunlight converted santonin to a yellow photoproduct: An early example of a precipitate was the photodimerization...

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Artemisin

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Artemisin is a sesquiterpene lactone, similar in structure to α-santonin. Artemisia (genus), hardy herbaceous plants and shrubs known for the powerful...

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Pfizer

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in Williamsburgh, New York where they produced an antiparasitic called santonin. This was an immediate success, although it was production of citric acid...

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Photochemistry

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described by Trommsdorff in 1834. He observed that crystals of the compound α-santonin when exposed to sunlight turned yellow and burst. In a 2007 study the reaction...

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Kailas Nath Kaul

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Kashmir caused yields of Santonin, an anthelminthic derived from the plant, to increase six times. This made the production of Santonin economically viable...

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Artemisia cina

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daisy family. Its dried flowerheads are the source of the vermifugic drug santonin since ancient times. Its common names arise from its known ability to expel...

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Anthelmintic

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design. Dysphania ambrosioides, an herb native to Central and South America Santonin, a historical anthelmintic no longer in use 4-Hexylresorcinol Praslicka...

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Charles Pfizer

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preparations, and citric acid for softdrink production. They also produced santonin, an antiparasitic, later expanding production to other chemicals. Pfizer's...

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Julius von Mayer

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invented Mayer's reagent which is used in detecting alkaloids. Ueber das Santonin : eine Inaugural-Dissertation, welche zur Erlangung der Doctorwürde in...

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Louis Merck

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CEO in 1897. During his tenure, the company held a virtual monopoly on santonin and cocaine. In 1905, he was appointed by Ernest Louis, Grand Duke of Hesse...

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Guido Bargellini

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chemistry, in particular, flavonoid dyes and coumarins, and the compound santonin. He was admitted to the Accademia dei Lincei in 1946. The Bargellini reaction...

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Edmund Rose

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for his research of color blindness, xanthopsia and the drug Santonin, and how Santonin affected color vision. In surgical medicine, he performed important...

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Artemisinin

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as a drug for systemic lupus erythematosus. Artemisia (genus) Artemisin Santonin Pharmacognosy Wang J, Xu C, Wong YK, Li Y, Liao F, Jiang T, Tu Y (2019)...

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List of drugs by year of discovery

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synthesis 1952 1820 Quinine (isolation) Woodward and Doering 1944 1830s Santonin 1832 Chloral hydrate Justus von Liebig 1832 1833 Diastase 1853 Acetylsalicylic...

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Artemisia pallens

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used as fodder, some of them are a source of the anthelmintic chemical santonin. Davana blossoms are offered to Shiva, the God of Transformation, by the...

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Ascariasis

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membranes. A saline cathartic would be administered several hours later. Santonin, more toxic than hexylresorcinol and often only partly effective. Oil of...

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Moxidectin

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quinolinium Pyrvinium benzylammonium Bephenium naphthalenesulfonate Suramin# Ascaridole‡ Hexylresorcinol Santonin‡ Tribendimidine Tetrachloroethylene‡...

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List of fungicides

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rabenzazole [Wikidata] ravuconazole saijunmao saisentong salicylanilide sanguinarine santonin seboctylamine sedaxane silthiofam [Wikidata] silver simeconazole [Wikidata]...

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Stanislao Cannizzaro

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his work on organic chemistry, which includes also an investigation of santonin, Cannizzaro rendered great service to chemistry with his 1858 paper Sunto...

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C15H18O3

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nonsteroidal anti-inflammatory drug Plicatin B, a hydroxycinnamic acid Santonin, a drug which was widely used in the past as an anthelminthic This set...

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Santonica

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may refer to: Santonica, the common name for a plant (Artemisia cina) Santonin, a drug formerly used to expel intestinal worms This disambiguation page...

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Organ pipe coral

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"ChemInform Abstract: Stereoselective Synthesis of 8,12-Furanoeudesmanes from Santonin. Absolute Stereochemistry of Natural Furanoeudesma-1,3-diene and Tubipofurane"...

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