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Santonin

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Name

Santonin

EINECS
CAS No. 481-06-1 Density 1.18g/cm3
Solubility Melting Point 172-173 °C(lit.)

Formula C15H18 O3 Boiling Point 423.4°Cat760mmHg
Molecular Weight 246.33 Flash Point 189.7°C
Transport Information Appearance
Safety Human poison by an unspecified route. Experimental poison by intravenous route. Moderately toxic experimentally by ingestion. It can cause disturbance of color vision. Objects first show bluish tinge, then yellow which is most prominent. Complete blindness may occur lasting perhaps for nearly a week. Dizziness, drowsiness, and nausea may also occur. Recovery is spontaneous. Combustible when exposed to heat or flame. When heated to decomposition it emits acrid smoke and irritating fumes. Risk Codes 22
Molecular Structure Molecular Structure of 481-06-1 (Naphtho[1,2-b]furan-2,8(3H,4H)-dione,3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3S,3aS,5aS,9bS)-) Hazard Symbols Toxic by ingestion, affects color vision.
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

 

Chemistry

IUPAC Name: 3,5A,9-Trimethyl-3a,4,5,9b-tetrahydro-3H-benzo[g][1]benzofuran-2,8-dione
The MF of Santonin (CAS NO.481-06-1) is C15H18O3.

                   
The MW of Santonin (CAS NO.481-06-1) is 246.3.
Synonyms of Santonin (CAS NO.481-06-1): [3S-(3a,3aa,5ab,9bb)]-3a,5,5a,9b-Tetrahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)-dione ; (-)-.alpha.-Santonin
Product Categories: Miscellaneous Natural Products
Index of Refraction: 1.552  
EINECS: 207-560-7
Density: 1.18 g/ml
Flash Point: 189.7 °C 
Boiling Point: 423.4 °C
Melting Point: 172-173 °C
Storage temp: 2-8 °C
Merck: 8361

History

The Encyclopedia Britannica (1911) notes that the typical dose was 2 to 5 grams. (It should be noted this was a total dose; many regimens called for 3 doses daily over 3 days, and the "3 teaspoons 3 times a day for 3 days" regimen was typical around the '50s when use of santonin was starting to wane; actual doses per dose were closer to 20-30 milligrams per adult dose in a typical "'50s regimen", but "one-shot" doses of santonin (especially via suppository) were common in the late 1800s-early 1900s.) The only formerly registered British preparation (as of 1911) was the "trochiscus santonini" (santonin lozenge), but the preparation "sodii santoninas" (soda of santonin) was also formerly listed as an official preparation in the U.S. Pharmacopoeia. Commercial preparations containing santonin (usually containing a purgative laxative as well) also appeared in US drug formularies as late as the '50s; the Modern Drug Encyclopedia and Therapeutic Index of 1955 listed Lumbricide (produced by Massengill) and a generic santonin preparation made by Winthrop-Stearns (now Winthrop-Sanofi).

Uses

 Santonin (CAS NO.481-06-1) is a drug which was widely used in the past as an anthelminthic, a drug that expels parasitic worms (helminths) from the body, by either killing or stunning them. Santonin was formerly listed in U.S. and British pharmacopoeia but has fallen out of use with the development of safer ascaricides and is no longer registered as a drug in most countries.
 As noted above, santonin was formerly used as an anthelminthic, typically administered with a purgative. Santonin was used in treatment of infestation by the roundworm Ascaris lumbricoides and in ascarid parasitoses in general (including threadworm parasitosis). It is ineffective in treatment of tapeworm infestation.

Toxicity Data With Reference

1.    

unr-man LDLo:15 mg/kg

    85DCAI    Poisoning; Toxicology, Symptoms, Treatments. 2 (1970),73.
2.    

orl-mus LD50:900 mg/kg

    NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982” Edited by Japan Pharmaceutical Information Center. 6 (1982),301.
3.    

ivn-mus LD50:180 mg/kg

    CSLNX*    U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#02213 .

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Human poison by an unspecified route. Experimental poison by intravenous route. Moderately toxic experimentally by ingestion. It can cause disturbance of color vision. Objects first show bluish tinge, then yellow which is most prominent. Complete blindness may occur lasting perhaps for nearly a week. Dizziness, drowsiness, and nausea may also occur. Recovery is spontaneous. Combustible when exposed to heat or flame. When heated to decomposition it emits acrid smoke and irritating fumes.Safety information of Santonin (CAS NO.481-06-1):
Hazard Codes  HarmfulXn
Risk Statements 
22 Harmful if swallowed
Safety Statements 
22 Do not breathe dust
24/25 Avoid contact with skin and eyes
RIDADR  2811
WGK Germany  3
RTECS  LE3150000
HazardClass  6.1(a)
PackingGroup  II

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.

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