16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-12-one

• ChemBase ID: 102987
• Molecular Formular: C23H22O6
• Molecular Mass: 394.41718
• Monoisotopic Mass: 394.14163842
• SMILES: COc1cc2c(cc1OC)C1C(CO2)Oc2c3CC(Oc3ccc2C1=O)C(=C)C
• Canonical SMILES: COc1cc2c(cc1OC)OCC1C2C(=O)c2c(O1)c1CC(Oc1cc2)C(=C)C
• InChI: InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3
• InChIKey: JUVIOZPCNVVQFO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 16,17-dimethoxy-6-(prop-1-en-2-yl)-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3,8,10,14(19),15,17-hexaen-12-one
• IUPAC Traditional name: rotenone
• Synonyms: Barbasco; Extrax; Rotocide; Tubatoxin; Cube root extract; Fish-tox; Cube extract; ROTENONE

Database IDs

• CAS Number: 83-79-4
• EC Number: 201-501-9
• PubChem SID: 162090317
• PubChem CID: 5102

CALCULATED PROPERTIES

• Acid pKa: 11.803546
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 3.3201776
• LogD (pH = 7.4): 3.3201606
• Log P: 3.3201778
• Molar Refractivity: 105.712296 cm^3
• Polarizability: 41.12286 Å^3
• Polar Surface Area: 63.22 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 165-166°C
• Boiling Point: 210-220°C
• Vapor Pressure: <1 x 10-5 mbar at 20 °C

Safety Information

• Storage Condition: Room Temperature (15-30°C), Store Under Nitrogen, Protect from light
• RTECS: DJ2800000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2811
• Hazard Class: 6.1
• Packing Group: III
• Australian Hazchem: 2X
• Risk Statements: R:25-36/37/38-50/53
• Safety Statements: S:22-36-45-60-61-24/25
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154

Product Information

• Purity: ≥97%

DETAILS

MP Biomedicals - 02150154

Purity: >97%
Crystalline
Respiratory inhibitor. Induces mammary adenomas.

REFERENCES

• Cancer Res. , 33 : 3047, (1973).