Caffeic Acid Phenethyl Ester (CAPE): Synthesis and X-Ray Crystallographic Analysis
The structure of caffeic acid phenethyl ester [2-propenoic acid, 3-(3, 4-dihydroxyphenyl)-, 2-phenethyl ester] (I), C17H16O4·1/2C6H6, synthesized by base-catalyzed alkylation of caffeic acid salt with β-bromoethylbenzene in HMPA (hexamethylphosphoramide) and recrystallized from benzene, was confirme...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2001, Vol.49(2), pp.236-238 |
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| creator | SON, Sopheak LOBKOWSKY, Emil B. LEWIS, Betty A. |
| description | The structure of caffeic acid phenethyl ester [2-propenoic acid, 3-(3, 4-dihydroxyphenyl)-, 2-phenethyl ester] (I), C17H16O4·1/2C6H6, synthesized by base-catalyzed alkylation of caffeic acid salt with β-bromoethylbenzene in HMPA (hexamethylphosphoramide) and recrystallized from benzene, was confirmed by single crystal X-ray diffraction. The crystals are triclinic, space group P 1, Z=2, unit cell dimension a=5.8129 (9) Å, b=11.122 (2) Å, c=13.226 (2) Å, α=97.080 (3)°, β=101.467 (3)°, γ=95.405 (3)°, V=825.4 (2) Å3, Dcalc=1.301 g/cm3, F(000)=342. The packing of the molecule is stabilized by intermolecular O1H…O4 (2.69 Å) and O1…HO2 (2.82 Å) hydrogen bonds. |
| doi_str_mv | 10.1248/cpb.49.236 |
| format | Article |
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The crystals are triclinic, space group P 1, Z=2, unit cell dimension a=5.8129 (9) Å, b=11.122 (2) Å, c=13.226 (2) Å, α=97.080 (3)°, β=101.467 (3)°, γ=95.405 (3)°, V=825.4 (2) Å3, Dcalc=1.301 g/cm3, F(000)=342. The packing of the molecule is stabilized by intermolecular O1H…O4 (2.69 Å) and O1…HO2 (2.82 Å) hydrogen bonds.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.49.236</identifier><identifier>PMID: 11217116</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds ; alkylation reaction ; caffeic acid phenethyl ester ; Caffeic Acids - chemical synthesis ; Caffeic Acids - chemistry ; Condensed matter: structure, mechanical and thermal properties ; Crystallography, X-Ray ; Exact sciences and technology ; hydroxycinnamic acid derivative ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Organic compounds ; phenolic compound ; Phenylethyl Alcohol - analogs & derivatives ; Phenylethyl Alcohol - chemical synthesis ; Phenylethyl Alcohol - chemistry ; Physics ; Spectrophotometry, Infrared ; Structure of solids and liquids; crystallography ; Structure of specific crystalline solids ; X-ray diffraction</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2001, Vol.49(2), pp.236-238</ispartof><rights>2001 The Pharmaceutical Society of Japan</rights><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=914186$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11217116$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>SON, Sopheak</creatorcontrib><creatorcontrib>LOBKOWSKY, Emil B.</creatorcontrib><creatorcontrib>LEWIS, Betty A.</creatorcontrib><title>Caffeic Acid Phenethyl Ester (CAPE): Synthesis and X-Ray Crystallographic Analysis</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>The structure of caffeic acid phenethyl ester [2-propenoic acid, 3-(3, 4-dihydroxyphenyl)-, 2-phenethyl ester] (I), C17H16O4·1/2C6H6, synthesized by base-catalyzed alkylation of caffeic acid salt with β-bromoethylbenzene in HMPA (hexamethylphosphoramide) and recrystallized from benzene, was confirmed by single crystal X-ray diffraction. The crystals are triclinic, space group P 1, Z=2, unit cell dimension a=5.8129 (9) Å, b=11.122 (2) Å, c=13.226 (2) Å, α=97.080 (3)°, β=101.467 (3)°, γ=95.405 (3)°, V=825.4 (2) Å3, Dcalc=1.301 g/cm3, F(000)=342. The packing of the molecule is stabilized by intermolecular O1H…O4 (2.69 Å) and O1…HO2 (2.82 Å) hydrogen bonds.</description><subject>Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds</subject><subject>alkylation reaction</subject><subject>caffeic acid phenethyl ester</subject><subject>Caffeic Acids - chemical synthesis</subject><subject>Caffeic Acids - chemistry</subject><subject>Condensed matter: structure, mechanical and thermal properties</subject><subject>Crystallography, X-Ray</subject><subject>Exact sciences and technology</subject><subject>hydroxycinnamic acid derivative</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Structure</subject><subject>Organic compounds</subject><subject>phenolic compound</subject><subject>Phenylethyl Alcohol - analogs & derivatives</subject><subject>Phenylethyl Alcohol - chemical synthesis</subject><subject>Phenylethyl Alcohol - chemistry</subject><subject>Physics</subject><subject>Spectrophotometry, Infrared</subject><subject>Structure of solids and liquids; crystallography</subject><subject>Structure of specific crystalline solids</subject><subject>X-ray diffraction</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkUtLw0AUhQdRbK1u_AESEEQXqfNKJ-NGSqgPKFiqgrswmbljUqZpnUkX-femtNbNuXDPx4F7LkKXBA8J5em9XhdDLoeUjY5QnzAu4oRSdoz6GGMZd2vWQ2chLDCmCRbsFPUIoUQQMuqjeaashUpHY12ZaFZCDU3ZumgSGvDRbTaeTe4eove2bkoIVYhUbaKveK7aKPNtaJRzq2-v1uU2oVau7ZhzdGKVC3CxnwP0-TT5yF7i6dvzazaexguW0iaWzBhGMQjOktQSq4oEjNBMUI7BWmu0wdJYDtQIkci04JJ2YoEoTlkxYgN0s8td-9XPBkKTL6ugwTlVw2oTcoETyUaEduDVHtwUSzD52ldL5dv8r4UOuN4DKmjlrFe1rsKBk4STdEs97qhFd_c3HGzlm0o7yLs35FzmdCdd7f9OqXwONfsFmzWAaA</recordid><startdate>20010201</startdate><enddate>20010201</enddate><creator>SON, Sopheak</creator><creator>LOBKOWSKY, Emil B.</creator><creator>LEWIS, Betty A.</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20010201</creationdate><title>Caffeic Acid Phenethyl Ester (CAPE): Synthesis and X-Ray Crystallographic Analysis</title><author>SON, Sopheak ; LOBKOWSKY, Emil B. ; LEWIS, Betty A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-j382t-93dd320e74358f1fab5ed7c37240efffdcd09df4e2d77598b4928b4fe1a423b63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds</topic><topic>alkylation reaction</topic><topic>caffeic acid phenethyl ester</topic><topic>Caffeic Acids - chemical synthesis</topic><topic>Caffeic Acids - chemistry</topic><topic>Condensed matter: structure, mechanical and thermal properties</topic><topic>Crystallography, X-Ray</topic><topic>Exact sciences and technology</topic><topic>hydroxycinnamic acid derivative</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Structure</topic><topic>Organic compounds</topic><topic>phenolic compound</topic><topic>Phenylethyl Alcohol - analogs & derivatives</topic><topic>Phenylethyl Alcohol - chemical synthesis</topic><topic>Phenylethyl Alcohol - chemistry</topic><topic>Physics</topic><topic>Spectrophotometry, Infrared</topic><topic>Structure of solids and liquids; crystallography</topic><topic>Structure of specific crystalline solids</topic><topic>X-ray diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>SON, Sopheak</creatorcontrib><creatorcontrib>LOBKOWSKY, Emil B.</creatorcontrib><creatorcontrib>LEWIS, Betty A.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>SON, Sopheak</au><au>LOBKOWSKY, Emil B.</au><au>LEWIS, Betty A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Caffeic Acid Phenethyl Ester (CAPE): Synthesis and X-Ray Crystallographic Analysis</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2001-02-01</date><risdate>2001</risdate><volume>49</volume><issue>2</issue><spage>236</spage><epage>238</epage><pages>236-238</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>The structure of caffeic acid phenethyl ester [2-propenoic acid, 3-(3, 4-dihydroxyphenyl)-, 2-phenethyl ester] (I), C17H16O4·1/2C6H6, synthesized by base-catalyzed alkylation of caffeic acid salt with β-bromoethylbenzene in HMPA (hexamethylphosphoramide) and recrystallized from benzene, was confirmed by single crystal X-ray diffraction. The crystals are triclinic, space group P 1, Z=2, unit cell dimension a=5.8129 (9) Å, b=11.122 (2) Å, c=13.226 (2) Å, α=97.080 (3)°, β=101.467 (3)°, γ=95.405 (3)°, V=825.4 (2) Å3, Dcalc=1.301 g/cm3, F(000)=342. The packing of the molecule is stabilized by intermolecular O1H…O4 (2.69 Å) and O1…HO2 (2.82 Å) hydrogen bonds.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>11217116</pmid><doi>10.1248/cpb.49.236</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds alkylation reaction caffeic acid phenethyl ester Caffeic Acids - chemical synthesis Caffeic Acids - chemistry Condensed matter: structure, mechanical and thermal properties Crystallography, X-Ray Exact sciences and technology hydroxycinnamic acid derivative Magnetic Resonance Spectroscopy Molecular Structure Organic compounds phenolic compound Phenylethyl Alcohol - analogs & derivatives Phenylethyl Alcohol - chemical synthesis Phenylethyl Alcohol - chemistry Physics Spectrophotometry, Infrared Structure of solids and liquids crystallography Structure of specific crystalline solids X-ray diffraction |
| title | Caffeic Acid Phenethyl Ester (CAPE): Synthesis and X-Ray Crystallographic Analysis |
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