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Substance Name: Santonin [JAN:NF]
RN: 481-06-1
UNII: 1VL8J38ERO
InChIKey: XJHDMGJURBVLLE-BOCCBSBMSA-N

Note

  • Anthelmintic isolated from the dried unexpanded flower heads of Artemisia maritima and other species of Artemisia found principally in Russian and Chinese Turkestan and the Southern Ural region. (From Merck, 11th ed.).

Molecular Formula

  • C15-H18-O3

Molecular Weight

  • 246.3042
 

Classification Codes

  • Anthelmintics
  • Anti-Infective Agents
  • Antinematodal Agents
  • Antiparasitic Agents
  • Human Data
  • Natural Product
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Names and Synonyms

Name of Substance

  • Santonin
  • Santonin [JAN:NF]

MeSH Heading

  • Santonin

Synonyms

  • (-)-Santonine
  • (3S)-2,3,3a,4,5,5a,8,9bbeta-Octahydro-3,5abeta,9-trimethylnaphtho(1,2-b)furan-2,8-dion
  • 11-Epiisoeusantona-1,4-dienic acid, 6alpha-hydroxy-3-oxo-, gamma-lactone
  • AI3-19471
  • alpha-Santonin
  • EINECS 207-560-7
  • Eudesma-1,4-dien-12-oic acid, 6-alpha-hydroxy-3-oxo-, gamma-lactone, (11S)-(-)-
  • L-alpha-Santonin
  • Naphtho(1,2-b)puran-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-
  • NSC 41311
  • NSC 4900
  • Santonin
  • Santoninic anhydride
  • Santoninum
  • Semenen
  • UNII-1VL8J38ERO

Systematic Names

  • (3S,3aS,5aS,9bS)-2,3,3a,4,5,5a,8,9b-Octahydro-3,5a,9-trimethylnaphtho(1,2-b)furan-2,8-dione
  • Eudesma-1,4-dien-12-oic acid, 6-alpha-hydroxy-3-oxo-, gamma-lactone, (11S)-
  • Naphtho(1,2-b)furan-2,8(3H,4H)-dione, 3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3S,3aS,5aS,9bS)-

Registry Numbers

CAS Registry Number

  • 481-06-1

FDA UNII

  • 1VL8J38ERO

Other Registry Number

  • 881738-49-4

System Generated Number

  • 0000481061

Structure Descriptors

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

InChIKey

XJHDMGJURBVLLE-BOCCBSBMSA-N

Smiles

C[C@H]1[C@@H]2CC[C@@]3(C)C=CC(=O)C(=C3[C@H]2OC1=O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man LDLo unreported 15mg/kg (15mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LD50 intraperitoneal 130mg/kg (130mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 52, Pg. 79S, 1956.
mouse LD50 intravenous 180mg/kg (180mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02213,
mouse LD50 oral 900mg/kg (900mg/kg)   Drugs in Japan Vol. 6, Pg. 301, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 175 deg C   EXP
log P (octanol-water) 1.780 (none)   EST
Water Solubility 200 mg/L   EXP
Vapor Pressure 2.38E-06 mm Hg 25 EST
Henry's Law Constant 5.27E-08 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 5.83E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.