Home > Name List By n > Naphtho[1,2-b]furan-2,8(3H,4H)-dione,3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3S,3aS,5aS,9bS)-

CAS No 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)-

  • 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: (-)-Santonin; Semenen; NSC 4900; a-Santonin;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;Naphtho[1,2-b]furan-2,8(3H,4H)-dione,3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3S,3aS,5aS,9bS)-;Eudesma-1,4-dien-12-oicacid, 6a-hydroxy-3-oxo-, g-lactone, (11S)- (8CI); (-)-a-Santonin;1,2,3,4,4a,7-Hexahydro-1-hydroxy-a,4a,8-trimethyl-7-oxo-2-naphthaleneacetic acid g-lactone;
  • CAS Registry Number:
  • 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)
  • Safety Statements: 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.
  • Hazard Symbols: Toxic by ingestion, affects color vision.
  • Flash Point: 189.7°C
  • EINECS: 207-560-7
  • 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
  • Risk Statements: 22
  • Molecular Formula: C15H18 O3
  • Molecular Structure:CAS No: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)-

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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)-

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481-06-1 (-)-ALPHA-SANTONIN 98% FW 246.3

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References of Naphtho[1,2-b]furan-2,8(3H,4H)-dione,3a,5,5a,9b-tetrahydro-3,5a,9-trimethyl-, (3S,3aS,5aS,9bS)-
Title: a-Santonin
CAS Registry Number: 481-06-1
CAS Name: [3S-(3a,3aa,5ab,9bb)]-3a,5,5a,9b-Tetrahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)-dione
Synonyms: 1,2,3,4,4a,7-hexahydro-1-hydroxy-a,4a,8-trimethyl-7-oxo-2-naphthaleneacetic acid g-lactone; l-santonin
Molecular Formula: C15H18O3
Molecular Weight: 246.30
Percent Composition: C 73.15%, H 7.37%, O 19.49%
Literature References: Anthelmintic isolated from the dried unexpanded flower heads of Artemisia maritima L., sens. lat., Compositae [Levant wormseed] and other species of Artemisia found principally in Russian and Chinese Turkestan and the Southern Ural region. Structure: Clemo et al., J. Chem. Soc. 1930, 1110; Ruzicka, Steiner, Helv. Chim. Acta 17, 614 (1934). Stereochemistry: Corey, J. Am. Chem. Soc. 77, 1044 (1955); Cocker, McMurry, Tetrahedron 8, 181 (1960); Asher, Sim, Proc. Chem. Soc. London 1962, 111, 335; Nakazaki, Arakawa, Bull. Chem. Soc. Jpn. 37, 464 (1964); Pregosin et al., J. Chem. Soc. Perkin Trans. 1 1972, 299. Total synthesis: Abe et al., Proc. Jpn. Acad. 30, 116 (1954); J. Am. Chem. Soc. 78, 1422 (1956); US 2836604 (1958 to Takeda); J. A. Marshall, P. G. M. Wuts, J. Org. Chem. 43, 1086 (1978). Mass spectral studies of the santonins and derivs: Woseda et al., Tetrahedron 23, 4623 (1967). Review: C. H. Heathcock in The Total Synthesis of Natural Products vol. 2, J. W. ApSimon, Ed. (Wiley, New York, 1973) pp 315-324.
 
Derivative Type: (-)-Form
Properties: Tabular crystals, orthorhombic sphenoidal, mp 170-173°. Almost tasteless with bitter aftertaste. [a]D25 -170 to -175° (c = 2 in alc). Becomes yellow on exposure to light. Irritating to mucous membranes. d 1.187. One part dissolves in 5000 parts of cold water, in 250 parts of boiling water, in 280 parts of 50% alcohol at 17°, in 10 parts of boiling 50% alcohol, in 44 parts of cold 90% alcohol, in 3 parts of boiling 90% alcohol, in 125 parts of cold ether, in 72 parts of boiling ether, in 4.3 parts of cold chloroform.
Melting point: mp 170-173°
Optical Rotation: [a]D25 -170 to -175° (c = 2 in alc)
Density: d 1.187
 
Derivative Type: (±)-Form
Properties: Colorless plates from methanol, mp 181°. uv max (ethanol): 241 nm (log e 4.10).
Melting point: mp 181°
Absorption maximum: uv max (ethanol): 241 nm (log e 4.10)
 
Derivative Type: (+)-Form
Properties: Colorless plates from methanol, mp 172°. [a]D20 +165.9° (c = 1.92 in ethanol).
Melting point: mp 172°
Optical Rotation: [a]D20 +165.9° (c = 1.92 in ethanol)
 
Derivative Type: 4-Hydroxysantonin see Artemisin
 
Therap-Cat: Anthelmintic (Nematodes).
Therap-Cat-Vet: Has been used as an anthelmintic.
Keywords: Anthelmintic (Nematodes).