(3S,3aS,5aS,9bS)-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,8H,9bH-naphtho[1,2-b]furan-2,8-dione

• ChemBase ID: 132463
• Molecular Formular: C15H18O3
• Molecular Mass: 246.30162
• Monoisotopic Mass: 246.12559444
• SMILES: C[C@H]1[C@@H]2CC[C@]3(C=CC(=O)C(=C3[C@H]2OC1=O)C)C
• Canonical SMILES: C[C@@H]1C(=O)O[C@H]2[C@H]1CC[C@@]1(C2=C(C)C(=O)C=C1)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,8H,9bH-naphtho[1,2-b]furan-2,8-dione
• IUPAC Traditional name: (-)-santonin; (3S,3aS,5aS,9bS)-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,8H,9bH-naphtho[1,2-b]furan-2,8-dione
• Synonyms: (3S,5aS,9bS)-3a,5,5a,9b-Tetrahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)dione; (-)-α-Santonin; Alpha-Santonin; Santonin

Database IDs

• CAS Number: 481-06-1
• EC Number: 207-560-7
• MDL Number: MFCD00135865
• Beilstein Number: 89489
• PubChem SID: 162226740; 24888233; 24899466
• PubChem CID: 221071

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.6011767
• LogD (pH = 7.4): 2.6011767
• Log P: 2.6011767
• Molar Refractivity: 68.8324 cm^3
• Polarizability: 26.52878 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 170-173 °C; 172-173 °C(lit.)
• Optical Rotation: [α]20/D -170±5°, c = 1% in ethanol

Safety Information

• RTECS: LE3150000
• European Hazard Symbols: Highly toxic (T+); Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 26/27/28-36/37/38
• Safety Statements: 26-28-36-37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H310-H315-H319-H330-H335
• GHS Precautionary statements: P260-P280-P284-P302 + P350-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Gabergic and cholinergic mechanisms

Product Information

• Purity: ≥97% (HPLC); ≥98.0% (CH); ≥99%
• Grade: analytical standard
• Biological Source: Occurs widely in plants, especially Artemisia spp.
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Anthelmintic
• Empirical Formula (Hill Notation): C15H18O3

DETAILS

Sigma Aldrich - S1250

包装
5, 10 g in glass bottle

Sigma Aldrich - 84508

Other Notes
Chiral building block used for the synthesis of various sesquiterpenoides1,2,3

REFERENCES

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 1, 709B, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 1, 1143C, (nmr)
• Pinhey, J.T. et al., Aust. J. Chem., 1965, 18, 543, (pmr)
• Asher, J.D.M. et al., J.C.S., 1965, 6041, (cryst struct)
• Boocock, D.G.B. et al., Chem. Comm., 1966, 90, (ms)
• Coggan, P. et al., J.C.S.(B), 1969, 237, (cryst struct)
• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, no. 1903, (occur)
• Heathcock, C.H., The Total Synthesis of Natural Products, (ApSimon, J.W., Ed.), Wiley, N.Y., 1973, 2, 315, (rev)
• Marshall, J.A. et al., J.O.C., 1978, 43, 1086, (synth)
• El-Feraly, F.S. et al., J.C.S. Perkin 1, 1983, 355, (synth)
• Kutney, J.P. et al., Can. J. Chem., 1984, 62, 2813, (synth)
• Van Hijfte, L. et al., Tetrahedron, 1984, 40, 4371, (synth)
• Shimizu, N. et al., Chem. Pharm. Bull., 1994, 42, 1160, (synth)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, SAU500