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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 421073479 |
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| Reference=<ref name="Merck">'']'', 11th Edition, '''4442'''</ref><ref name="Science">''Science. '''1969''', ''vol. 166'' pp.1010-1012</ref> |
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| verifiedrevid = 450502843 |
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| Name = Grandisol |
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| Reference = <ref name="Merck">'']'', 11th Edition, '''4442'''</ref><ref name="Science">''Science.'' '''1969''', vol. 166 pp.1010-1012</ref> |
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| ImageFile = Grandisol.png |
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| Name = Grandisol |
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| ImageSize = 120px |
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| ImageFile = Grandisol.png |
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| ImageName = |
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| ImageSize = 140px |
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| IUPACName =<small>(+)-(1''R'',2''S'')-1-(2'-Hydroxyethyl)-1-methyl-<br />2-isopropenylcyclobutane</small> |
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| ImageAlt = Skeletal formula of grandisol |
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| OtherNames =<small>''cis''-2-Isopropenyl-1-methylcyclobutaneethanol</small> |
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| ImageFile1 = Grandisol 3D ball.png |
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| Section1 = {{Chembox Identifiers |
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| ImageSize1 = 160 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ImageAlt1 = Ball-and-stick model of the grandisol molecule |
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| PIN = 2-ethan-1-ol |
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| OtherNames = ''cis''-2-Isopropenyl-1-methylcyclobutaneethanol |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 147990 |
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| ChemSpiderID = 147990 |
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| PubChem = 169202 |
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| PubChem = 169202 |
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| InChI = 1/C10H18O/c1-8(2)9-4-5-10(9,3)6-7-11/h9,11H,1,4-7H2,2-3H3/t9-,10+/m0/s1 |
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| InChIKey = SJKPJXGGNKMRPD-VHSXEESVBS |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C10H18O/c1-8(2)9-4-5-10(9,3)6-7-11/h9,11H,1,4-7H2,2-3H3/t9-,10+/m0/s1 |
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| StdInChI = 1S/C10H18O/c1-8(2)9-4-5-10(9,3)6-7-11/h9,11H,1,4-7H2,2-3H3/t9-,10+/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = SJKPJXGGNKMRPD-VHSXEESVSA-N |
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| StdInChIKey = SJKPJXGGNKMRPD-VHSXEESVSA-N |
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| CASNo_Ref = {{cascite|changed|CAS}} |
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| CASNo = 28117-21-7 |
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| CASNo = 26532-22-9 |
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| SMILES = OCC1(C)(C(=C)C)CC1 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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}} |
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| UNII = 9S44Q9MKXB |
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| Section2 = {{Chembox Properties |
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| SMILES = OCC1(C)(C(=C)C)CC1 |
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| Formula = C<sub>10</sub>H<sub>18</sub>O |
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}} |
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| MolarMass = 154.25 g/mol |
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|Section2={{Chembox Properties |
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| Density = |
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| Formula = C<sub>10</sub>H<sub>18</sub>O |
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| MeltingPt =<25 °C |
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| MolarMass = 154.25 g/mol |
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| BoilingPt = 50-60 °C at 1 mmHg |
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| Density = |
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| MeltingPt=< |
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| MeltingPtC = 25 |
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| BoilingPtC = 50 to 60 |
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| BoilingPt_notes = at 1 mmHg |
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'''Grandisol''' is a natural ] with the ] C<sub>10</sub>H<sub>18</sub>O. It is a ] containing a ] ring, an ] group, an ] group and two ] centers (one of which is quaternary). |
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'''Grandisol''' is a natural ] with the ] C<sub>10</sub>H<sub>18</sub>O. It is a ] containing a ] ring, an ] group, an ] group and two ] centers (one of which is quaternary). |
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Grandisol is a ] primarily important as the sex attractant of the ] (''Anthonomus grandis''), from which it gets its name.<ref name="Merck"/> 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 ], which is used to protect cotton crops from the boll weevil.<ref name="Merck"/> |
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Grandisol is a ] primarily important as the sex attractant of the ] (''Anthonomus grandis''), from which it gets its name.<ref name="Merck"/> 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 ], which is used to protect cotton crops from the boll weevil.<ref name="Merck"/> |
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==Synthesis== |
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==Synthesis== |
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Grandisol was first isolated, identified, and synthesized by J. Tumlinson ''et al''. at Mississippi State University in 1969.<ref name="Science"/> The most recent and highest yielding synthetic route to grandisol was reported in January 2010 by a group of chemists at ]. <ref>{{cite journal |author=Graham, Thomas J.A.; Burgess, James M.; Gray, Erin; Goess, Brian C. |title=An Efficient Synthesis of (±)-Grandisol Featuring 1,5-Enyne Metathesis |journal=J. Org. Chem. |volume=75 |issue=1 |pages=226–228|year=2010 |month=January |pmid=19957923|pmc=2798917|doi=10.1021/jo9020375 |url=http://pubs.acs.org/doi/abs/10.1021/jo9020375}}</ref> 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.<ref>{{cite journal |author=Hibbard, B.; Webster, F. |title=Enantiomeric composition of grandisol and grandisl produced by Pissodes strobi and P. nemorensis and their electroantennogram response to pure enantiomers |journal=J. Chem. Ecol. |volume=19 |issue=10 |pages=2129–2141|year=1993 |month=October |pmid=|pmc=|doi=10.1007/BF00979652 |url=http://www.springerlink.com/content/n666313620244460/}}</ref> |
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Grandisol was first isolated, identified, and synthesized by J. Tumlinson ''et al''. at Mississippi State University in 1969.<ref name="Science"/> The most recent and highest yielding synthetic route to grandisol was reported in January 2010 by a group of chemists at ].<ref>{{cite journal |author1=Graham, Thomas J.A. |author2=Gray, Erin E. |author3=Burgess, James M. |author4=Goess, Brian C. |title=An Efficient Synthesis of (±)-Grandisol Featuring 1,5-Enyne Metathesis |journal=J. Org. Chem. |volume=75 |issue=1 |pages=226–228|date=January 2010 |pmid=19957923|pmc=2798917|doi=10.1021/jo9020375 }}</ref> 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.<ref>{{cite journal |author1=Hibbard, B. |author2=Webster, F. |title=Enantiomeric composition of grandisol and grandisl produced by Pissodes strobi and P. nemorensis and their electroantennogram response to pure enantiomers |journal=J. Chem. Ecol. |volume=19 |issue=10 |pages=2129–2141|date=October 1993 |pmid=24248564|doi=10.1007/BF00979652 |s2cid=31951106 }}</ref> |
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==References== |
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== References == |
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