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Dihydroactinidiolide

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Dihydroactinidiolide
Skeletal formula of dihydroactinidiolide
Ball-and-stick model of the dihydroactinidiolide molecule
Names
Preferred IUPAC name (7aR)-4,4,7a-Trimethyl-5,6,7,7a-tetrahydro-1-benzofuran-2(4H)-one
Other names Dihydroactinidiolide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.169.249 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C11H16O2/c1-10(2)5-4-6-11(3)8(10)7-9(12)13-11/h7H,4-6H2,1-3H3/t11-/m1/s1Key: IMKHDCBNRDRUEB-LLVKDONJSA-N
  • InChI=1/C11H16O2/c1-10(2)5-4-6-11(3)8(10)7-9(12)13-11/h7H,4-6H2,1-3H3/t11-/m1/s1Key: IMKHDCBNRDRUEB-LLVKDONJBM
SMILES
  • O=C2O1(C)CCCC(C)(C)C1=C2
  • O=C\1O2(/C(=C/1)C(CCC2)(C)C)C
Properties
Chemical formula C11H16O2
Molar mass 180.24 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Dihydroactinidiolide is a volatile terpene. It has a sweet, tea-like odor and is used as a fragrance. Dihydroactinidiolide occurs naturally in black tea, fenugreek, fire ants, mangoes, and tobacco. It has also been prepared synthetically.

Dihydroactinidiolide is a pheromone for a variety of insects; for example, it is one of the three components of the pheromone for queen recognition of the workers of the red fire ant.

References

  1. S. Yao, M. Johannsen, R.G. Hazell, K.A. Jorgensen, J. Org. Chem., 63, 118-121.
  2. Pherobase listing for dihydroactinidiolide
  3. Rocca, J.R. Tumlinson, J.H., Glancey, B.M., Lofgren, C.S., Tetrahedron Lett., 1983, 24, 1889.
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