Dihydroactinidiolide
Title: Dihydroactinidiolide
CAS Registry Number: 15356-74-8
CAS Name: 5,6,7,7a-Tetrahydro-4,4,7a-trimethyl-2(4H)-benzofuranone
Additional Names: 2-oxo-4,4,7a-trimethyl-2,4,5,6,6,7a-hexahydrobenzofuran; (2,6,6-trimethyl-2-hydroxycyclohexylidene)acetic acid lactone
Molecular Formula: C11H16O2
Molecular Weight: 180.24
Percent Composition: C 73.30%, H 8.95%, O 17.75%
Literature References: Found in many plant sources including tea and tobacco. (-)-Form is naturally occurring. Produced by photo-oxidation of carotenoid flavor compounds. Pheromone component for queen recognition in red fire ants. Isoln from black tea aroma: J. Bricout et al., Helv. Chim. Acta 50, 1517 (1967); from Actinidia polygama Miq. and structure determn: T. Sakan et al., Tetrahedron Lett. 8, 1623 (1967); from tobacco and synthesis: W. C. Bailey, Jr. et al., J. Org. Chem. 33, 2819 (1968). Synthesis: S. Isoe et al., Tetrahedron Lett. 9, 5561 (1968); by photo-oxidation of b-carotene: eidem, ibid. 10, 279 (1969). Abs config study: eidem, ibid. 13, 2517 (1972). Prepn of enantiomers: K. Mori, Y. Nakazono, Tetrahedron 42, 283 (1986). Improved prepns: G. V. Subbaraju et al., Tetrahedron Lett. 32, 4871 (1991); A. Bosser et al., Biotechnol. Prog. 11, 689 (1995). Prepn of (R)-form: S. Yao et al., J. Org. Chem. 63, 118 (1998). Germination inhibition in wheat grains: T. Kato et al., J. Agric. Food Chem. 51, 2161 (2003).
Properties: Tan oil, bp800 108-109°. mp 42-43°. Fruity aroma. uv max: 241 nm (e 10000).
Melting point: mp 42-43°
Boiling point: bp800 108-109°
Absorption maximum: uv max: 241 nm (e 10000)
 
Derivative Type: (R)-Form
CAS Registry Number: 17092-92-1
Properties: mp 70-71°. [a]D24 -121.0° (c = 1.05 in CHCl3).
Melting point: mp 70-71°
Optical Rotation: [a]D24 -121.0° (c = 1.05 in CHCl3)
 
Derivative Type: (S)-Form
CAS Registry Number: 81800-41-1
Properties: mp 67-68°. [a]D23 +120.9° (c = 1.00 in CHCl3).
Melting point: mp 67-68°
Optical Rotation: [a]D23 +120.9° (c = 1.00 in CHCl3)
 
Use: Flavor ingredient; inhibitor of seed germination.

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