7,9-ditert-butyl-1-oxaspiro[4.5]deca-6,9-diene-2,8-dione Chemical Properties

Melting point:

139-140 °C

Boiling point:

426.3±45.0 °C(Predicted)

Density 

1.06±0.1 g/cm3(Predicted)

storage temp. 

Amber Vial, -20°C Freezer, Under inert atmosphere

solubility 

Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)

form 

Solid

color 

White to Pale Yellow

Stability:

Light Sensitive

InChI

InChI=1S/C17H24O3/c1-15(2,3)11-9-17(8-7-13(18)20-17)10-12(14(11)19)16(4,5)6/h9-10H,7-8H2,1-6H3

InChIKey

ZTMZUYHXZPUDRF-UHFFFAOYSA-N

SMILES

O1C2(C=C(C(C)(C)C)C(=O)C(C(C)(C)C)=C2)CCC1=O

7,9-ditert-butyl-1-oxaspiro[4.5]deca-6,9-diene-2,8-dione Usage And Synthesis

Health Benifits

Chemical Properties

7,9-Ditert-butyl-1-oxaspiro[4.5]deca-6,9-diene-2,8-dione (C17H24O3, CAS registry No. 82304-66-3) is an oxaspiro compound that is 1-oxaspiro[4.5]deca-6,9-diene-2,8-dione carrying two additional tert-butyl substituents at positions 7 and 9. It is an oxaspiro compound with a lactone, an enone and a cyclic ketone. Its melting point is 139-140 °C.

Uses

7,9-Di-tert-butyl-1-oxaspiro[4.5]deca-6,9-diene-2,8-dione is an antioxidant naturally found in aerial parts of Gmelina asiatica Linn (Verbenaceae). It is also found in essential oils of some Stachys species from Mediterranean area. It is an impurity of Irganox 1098 (A697523) used in the food packaging.

Definition

ChEBI: 7,9-di-tert-butyl-1-oxaspiro[4.5]deca-6,9-diene-2,8-dione is an oxaspiro compound that is 1-oxaspiro[4.5]deca-6,9-diene-2,8-dione carrying two additional tert-butyl substituents at positions 7 and 9. It is an oxaspiro compound, a lactone, an enone and a cyclic ketone.

Synthesis

Compound 2b (0.1 g, 0.47 mmol) was dissolved in chloroform (5 ml) and triphenylphosphine (0.13 g, 0.49 mmol) was added. The reaction mixture was stirred and the progress of the reaction was monitored by TLC until complete disappearance of the peroxide (reaction time about 10-20 min). Subsequently, p-toluenesulfonic acid (9 mg, 0.05 mmol) was added and the reaction mixture was heated to 50 °C. After 4 hours of reaction, the mixture was concentrated to dryness under reduced pressure and purified directly by column chromatography to afford the target compound 7,9-di-tert-butyl-1-oxaspiro[4.5]deca-6,9-diene-2,8-dione (0.074 g, 87% yield). The product characterization data were as follows: IR (neat, cm-1): 2957, 1774, 1647; 1H NMR (500 MHz, CDCl3): δ6.51 (s, 2H), 2.77 (t, J=8.3 Hz, 2H), 2.28 (t, J=8.3 Hz, 2H), 1.23 (s, 18H); 13C NMR ( 125 MHz, CDCl3): δ 185.5, 175.8, 147.7, 137.1, 79.9, 34.9, 33.3, 29.3, 28.6; HRMS (ESI) calculated value of C17H24O3Na [M+Na]+: 299.161762, measured value: 299.161663.

References

[1] Tetrahedron Letters, 2013, vol. 54, # 25, p. 3294 - 3297