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Naphtho[1,2-b]furan-2,8(3H,4H)-dione,3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3S,3aS,5aS,9bS)- (481-06-1)

Identification
Name:Naphtho[1,2-b]furan-2,8(3H,4H)-dione,3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3S,3aS,5aS,9bS)-
Synonyms:Eudesma-1,4-dien-12-oicacid, 6a-hydroxy-3-oxo-, g-lactone, (11S)- (8CI);Naphtho[1,2-b]furan-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-,[3S-(3a,3aa,5ab,9bb)]-; (-)-Santonin; (-)-a-Santonin;1,2,3,4,4a,7-Hexahydro-1-hydroxy-a,4a,8-trimethyl-7-oxo-2-naphthaleneacetic acid g-lactone; NSC 4900; Santonin; Semenen; a-Santonin
CAS:481-06-1
EINECS: 207-560-7
Molecular Formula: C15H18 O3
Molecular Weight: 246.33
InChI: InChI=1/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
Molecular Structure: (C15H18O3) Eudesma-1,4-dien-12-oicacid, 6a-hydroxy-3-oxo-, g-lactone, (11S)- (8CI);Naphtho[1,2-b]furan-2,8(3H,4...
Properties
Transport:2811
Melting Point: 172-173 °C(lit.)
Flash Point: 189.7°C
Boiling Point: 423.4°Cat760mmHg
Density:1.18g/cm3
Refractive index:-172.5 ° (C=2, CHCl3)
Specification:

 Santonin can be converted to santonic acid (C15H20O4) via based-catalyzed hydrolysis followed by a multistep rearrangement process.
 Santonin was an agent which (compared to more modern anthelminthic drugs) was very complicated to use and entailed rather serious risk to the patient. Nearly every formulary and herbal which lists santonin or santonin-containing plants lists the real risk of yellow vision and of fatal reactions; even small doses of santonin cause disturbances of vision, usually yellow vision or perhaps green (xanthopsia or chromatopsia).
 While absinthe is certainly more infamous for its content of thujone, the liquor does also contain small amounts of santonin. It has been speculated by some parties that Impressionist art--in particular, Van Gogh's artwork--may have been inspired not by thujone and its presumed psychotropic effects, but on the "yellow vision" or xanthopsia which is a known side effect of santonin. This has been disputed, however, most notably by Arnold and Loftus (1991) who have noted the santonin content would have been insufficient to cause xanthopsia.

Report:

Reported in EPA TSCA Inventory.

Packinggroup: II
Flash Point: 189.7°C
Storage Temperature: 2-8°C
Safety Data
Hazard Symbols
 

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