| Revision as of 10:56, 16 December 2010 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi← Previous edit |
Latest revision as of 15:11, 24 January 2024 edit undoMaxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,042 edits Add: pmid, pages, issue, volume. |
| (31 intermediate revisions by 23 users not shown) |
| Line 1: |
Line 1: |
|
{{Orphan|date=February 2009}} |
|
|
{{chembox |
|
{{chembox |
|
|
|Verifiedfields = changed |
| ⚫ |
| verifiedrevid = 402673806 |
|
|
|
|Watchedfields = changed |
|
⚫ |
|verifiedrevid = 402674700 |
|
|
|ImageFile_Ref = {{chemboximage|correct|??}} |
|
|ImageFile=Solketal.png |
|
|ImageFile=Solketal.png |
|
|ImageSize=150px |
|
|ImageSize=150px |
|
|IUPACName=(2,2-dimethyl-1,3-dioxolan-4-yl)methanol |
|
|PIN=(2,2-Dimethyl-1,3-dioxolan-4-yl)methanol |
|
|OtherNames=Isopropylidene glycerol |
|
|OtherNames=Isopropylidene glycerol |
|
|Section1= {{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID = 7247 |
|
|ChemSpiderID = 7247 |
|
| InChI = 1/C6H12O3/c1-6(2)8-4-5(3-7)9-6/h5,7H,3-4H2,1-2H3 |
|
|InChI = 1/C6H12O3/c1-6(2)8-4-5(3-7)9-6/h5,7H,3-4H2,1-2H3 |
|
| InChIKey = RNVYQYLELCKWAN-UHFFFAOYAB |
|
|InChIKey = RNVYQYLELCKWAN-UHFFFAOYAB |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI = 1S/C6H12O3/c1-6(2)8-4-5(3-7)9-6/h5,7H,3-4H2,1-2H3 |
|
|StdInChI = 1S/C6H12O3/c1-6(2)8-4-5(3-7)9-6/h5,7H,3-4H2,1-2H3 |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChIKey = RNVYQYLELCKWAN-UHFFFAOYSA-N |
|
|StdInChIKey = RNVYQYLELCKWAN-UHFFFAOYSA-N |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
|CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo=100-79-8 |
|
|CASNo=100-79-8 |
|
|
|CASNo_Comment = Racemic |
| ⚫ |
| PubChem=7528 |
|
|
|
|CASNo1_Ref = {{cascite|changed|??}} |
|
| SMILES=CC1(OCC(O1)CO)C |
|
|
|
|CASNo1=14347-78-5 |
| ⚫ |
}} |
|
|
|
|CASNo1_Comment = ''R'' enantiomer |
|
|Section2= {{Chembox Properties |
|
|
|
|CASNo2_Ref = {{cascite|changed|??}} |
|
| Formula=C<sub>6</sub>H<sub>12</sub>O<sub>3</sub> |
|
|
|
|CASNo2=22323-82-6 |
|
| MolarMass=132.15768 |
|
|
|
|CASNo2_Comment = ''S'' enantiomer |
|
| Appearance= |
|
|
|
|UNII_Ref = {{fdacite|changed|FDA}} |
|
| Density= |
|
|
|
|UNII = 3XK098O8ZW |
|
| MeltingPt= |
|
|
⚫ |
|PubChem=7528 |
|
| BoilingPt=188-189 ºC |
|
|
|
|SMILES=OCC1COC(C)(C)O1 |
| ⚫ |
| Solubility=Miscible |
|
|
}} |
|
}} |
|
|Section3= {{Chembox Hazards |
|
|Section2={{Chembox Properties |
|
|
|C=6|H=12|O=3 |
|
| MainHazards= |
|
|
|
|Appearance=clear colorless liquid |
|
| FlashPt=80 ºC |
|
|
|
|Density=1.063 g/mL at 25 °C |
|
| Autoignition= |
|
|
|
|BoilingPtC=188 to 189 |
| ⚫ |
}} |
|
|
⚫ |
|Solubility=Miscible |
|
|
|SolubleOther = Miscible in most organic solvents (alcohols, ethers, hydrocarbons) |
|
⚫ |
}} |
|
|
|Section3={{Chembox Hazards |
|
|
|FlashPtC = 80 |
|
⚫ |
}} |
|
}} |
|
}} |
|
|
|
|
|
'''Solketal''' is a protected form of ] with an ] group bound to two neighboring ] groups. Solketal contains a chiral center on the center carbon of the glycerol backbone, and so can be purchased as either the ] or as one of the two ]s. Solketal has been used extensively in the synthesis of mono-, di- and tri]s by ester bond formation. The free hydroxyl groupd of solketal can be ] with a carboxylic acid to form the protected monoglyceride, where the isopropylene group can then be removed using an acid catalyst in aqueous or alcoholic medium. The unprotected ] can then be esterified further to form either the di- or triglyceride. |
|
'''Solketal''' is a protected form of ] with an ] group joining two neighboring ] groups. Solketal contains a chiral center on the center carbon of the glycerol backbone, and so can be purchased as either the ] or as one of the two ]s. Solketal has been used extensively in the synthesis of mono-, di- and tri]s by ester bond formation. The free hydroxyl group of solketal can be ] with a carboxylic acid to form the protected monoglyceride. The isopropylene group can then be removed using an acid catalyst in aqueous or alcoholic medium. The unprotected ] can then be esterified further to form either the di- or triglyceride. |
|
|
|
|
|
|
Another route to specific di- or triglycerides involves converting the solketal to ] (2,3-epoxy-1-propanol) and esterifying this with one fatty acid before opening the ] by heating in the presence of a second fatty acid and a catalyst. This second fatty acid is put on the third carbon atom, and then a third fatty acid can be added to the second carbon atom.<ref>{{cite journal |last1=C.M. Lok, J.P. Ward, D.A. van Dorp |title=The synthesis of Chiral Glycerides starting from D- and L-serine |journal=Chemistry and Physics of Lipids |date=Mar 1976 |volume=16 |issue=2 |pages=115–122 |doi=10.1016/0009-3084(76)90003-7|pmid=1269065 }}</ref> |
| ⚫ |
==References== |
|
|
Organic Syntheses, Coll. Vol. 3, p. 502, 1955 |
|
|
|
|
|
|
⚫ |
==References== |
|
The Journal of Organic Chemistry, 53, p. 2859, 1988 |
|
|
|
{{Reflist}} |
|
|
|
|
|
{{nofootnotes|date=July 2013}} |
| ⚫ |
{{cite web|title=Solketal|url=http://www.chemblink.com/products/100-79-8.htm|publisher=Logo of chemBlink Inc. Online Database of Chemicals from Around the World|archiveurl=http://www.webcitation.org/5tt3U6Xw6|archivedate=31 October 2010}} |
|
|
|
* {{OrgSynth|author=Mary Renoll and Melvin S. Newman |year=1955 |title=dl-ISOPROPYLIDENEGLYCEROL |volume=28 |pages=73 |collvol=3 |collvolpages=502 |prep=}} |
|
|
|
|
|
* {{cite journal | journal = Journal of Organic Chemistry | volume = 53 | pages = 2859 | year = 1988 | doi = 10.1021/jo00247a043 | title = Free radicals in organic synthesis. A novel synthesis of glycerol based on ethylene glycol and formaldehyde | last1 = Sanderson | first1 = John R. | last2 = Lin | first2 = Jiang J. | last3 = Duranleau | first3 = Roger G. | last4 = Yeakey | first4 = Ernest L. | last5 = Marquis | first5 = Edward T. | issue = 12}} |
|
Tetrahedron, 52, p. 9387, 1996 |
|
|
⚫ |
* {{cite web|title=Solketal|url=http://www.chemblink.com/products/100-79-8.htm|publisher=Logo of chemBlink Inc. Online Database of Chemicals from Around the World|archiveurl=https://web.archive.org/web/20101213022620/http://chemblink.com/products/100-79-8.htm|url-status=live|archivedate=13 December 2010}} |
|
|
* {{cite journal | journal = Tetrahedron | volume = 52 | pages = 9387 | year = 1996 | doi = 10.1016/0040-4020(96)00501-7 | title = Selective cleavage of ethers using silica-alumina gel catalysts prepared by the sol-gel method | last1 = Matsumoto | first1 = Yoshihiko | last2 = Mita | first2 = Keisuke | last3 = Hashimoto | first3 = Keiji | last4 = Iio | first4 = Hideo | last5 = Tokoroyama | first5 = Takashi | issue = 28}} |
|
|
|
|
|
] |
|
] |
|
|
] |