Grandisol

Title: Grandisol
CAS Registry Number: 26532-22-9
CAS Name: (1R-cis)-1-Methyl-2-(1-methylethenyl)cyclobutaneethanol
Additional Names: cis-(+)-2-isopropenyl-1-methylcyclobutaneethanol; (+)-(1R,2S)-1-(2¢-hydroxyethyl)-1-methyl-2-isopropenylcyclobutane
Molecular Formula: C10H18O
Molecular Weight: 154.25
Percent Composition: C 77.87%, H 11.76%, O 10.37%
Literature References: Major component of grandlure, the sex pheromone of the boll weevil (Anthonomus grandis, Boheman). Isoln and synthesis: J. H. Tumlinson et al., Science 166, 1010 (1969); eidem, J. Org. Chem. 36, 2616 (1971). Synthesis of optically active grandisol: P. D. Hobbs, P. D. Magnus, Chem. Commun. 1974, 856; eidem, J. Am. Chem. Soc. 98, 4594 (1976); K. Mori, Tetrahedron 34, 915 (1978); of enantiomerically pure grandisol: J. B. Jones et al., Can. J. Chem. 60, 2007 (1982). Synthesis of racemate: B. M. Trost et al., J. Am. Chem. Soc. 99, 3088 (1977). Short stereoselective synthesis of (±)-grandisol: I. Aljancic-Solaja et al., Helv. Chim. Acta 70, 1302 (1987). Review of syntheses: J. A. Katzenellenbogen, Science 194, 139-148 (1976); J. M. Brand et al., Fortschr. Chem. Org. Naturst. 37, 18-29 (1979), see also refs pp 157-190; K. Mori, "The Synthesis of Insect Pheromones" in The Total Synthesis of Natural Products vol. 4, J. ApSimon, Ed. (Wiley-Interscience, New York, 1981) pp 80-85.
Properties: Liquid, bp1.0 50-60°. [a]D21.5 +18.5° (c = 1 in hexane). nD20 1.4748.
Boiling point: bp1.0 50-60°
Optical Rotation: [a]D21.5 +18.5° (c = 1 in hexane)
Index of refraction: nD20 1.4748
Granisetron Granulocyte Colony-Stimulating Factor Granulocyte-Macrophage Colony-Stimulating Factor Graphite Fluoride Graphitic Acid

Grandisol[1][2]
Grandisol.png
Identifiers
CAS number 28117-21-7 YesY
PubChem 169202
ChemSpider 147990 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H18O
Molar mass 154.25 g/mol
Melting point <25 °C
Boiling point 50−60 °C at 1 mmHg
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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.[1] 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.[1]