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Grandisol

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Grandisol
Skeletal formula of grandisol
Ball-and-stick model of the grandisol molecule
Names
Preferred IUPAC name 2-ethan-1-ol
Other names cis-2-Isopropenyl-1-methylcyclobutaneethanol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H18O/c1-8(2)9-4-5-10(9,3)6-7-11/h9,11H,1,4-7H2,2-3H3/t9-,10+/m0/s1Key: SJKPJXGGNKMRPD-VHSXEESVSA-N
SMILES
  • OCC1(C)(C(=C)C)CC1
Properties
Chemical formula C10H18O
Molar mass 154.25 g/mol
Melting point < 25 °C (77 °F; 298 K)
Boiling point 50 to 60 °C (122 to 140 °F; 323 to 333 K) at 1 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Grandisol is a natural organic compound with the molecular formula C10H18O. It is a monoterpene containing a cyclobutane ring, an alcohol group, an alkene group and two chiral centers (one of which is quaternary).

Grandisol is a pheromone primarily important as the sex attractant of the cotton boll weevil (Anthonomus grandis), from which it gets its name. It is also a pheromone for other related insects. The cotton boll weevil is an agricultural pest that can cause significant economic damage if not controlled. Grandisol is the major constituent of the mixture known as grandlure, which is used to protect cotton crops from the boll weevil.

Synthesis

Grandisol was first isolated, identified, and synthesized by J. Tumlinson et al. at Mississippi State University in 1969. The most recent and highest yielding synthetic route to grandisol was reported in January 2010 by a group of chemists at Furman University. Though enantioselective syntheses have been reported, racemic grandisol has proven equally effective at attracting boll weevils as the natural enantiomer, rendering moot the need for enantioselective syntheses for agricultural purposes.

References

  1. ^ Merck Index, 11th Edition, 4442
  2. ^ Science. 1969, vol. 166 pp.1010-1012
  3. Graham, Thomas J.A.; Gray, Erin E.; Burgess, James M.; Goess, Brian C. (January 2010). "An Efficient Synthesis of (±)-Grandisol Featuring 1,5-Enyne Metathesis". J. Org. Chem. 75 (1): 226–228. doi:10.1021/jo9020375. PMC 2798917. PMID 19957923.
  4. Hibbard, B.; Webster, F. (October 1993). "Enantiomeric composition of grandisol and grandisl produced by Pissodes strobi and P. nemorensis and their electroantennogram response to pure enantiomers". J. Chem. Ecol. 19 (10): 2129–2141. doi:10.1007/BF00979652. PMID 24248564. S2CID 31951106.
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