SYNTHESIS OF (R)- AND (S)-1,2-DIACYLOXYPROPYL-3-ARSONIC ACIDS: OPTICALLY ACTIVE ARSONOLIPIDS
Reaction of trisodium arsenite with (R)- and (S)-glycidol affords in good yields the (R)- and (S)-1,2-dihydroxypropyl-3-arsonic acid, the tetrabutylammonium salt of which upon acylation with myristic, palmitic and stearic anhydrides in the presence of pyridine gives, in moderate to low yields, optic...
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| Veröffentlicht in: | Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 1992-10, Vol.71 (1-4), p.99-105 |
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| container_issue | 1-4 |
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| container_title | Phosphorus, sulfur, and silicon and the related elements |
| container_volume | 71 |
| creator | Serves, Spyros V. Tsivgoulis, Gerasimos M. Sotiropoulos, Demetrios N. Ioannou, Panayiotis V. Jain, Mahendra K. |
| description | Reaction of trisodium arsenite with (R)- and (S)-glycidol affords in good yields the (R)- and (S)-1,2-dihydroxypropyl-3-arsonic acid, the tetrabutylammonium salt of which upon acylation with myristic, palmitic and stearic anhydrides in the presence of pyridine gives, in moderate to low yields, optically active arsonolipids, i.e., (R)- and (S)-1,2-diacyloxypropyl-3-arsonic acids. The thermotropic phase transitions of these arsonolipids are characterized. Results show that the transition temperatures and enthalpies of fusion of the racemates are lower than those of the enantiomers in the powder form presumably because of conglomerate formation. The thermotropic transition characteristics of the aqueous dispersions of the arsonolipids change with the acyl chain lengths, and the overall behaviour is similar to that of the aqueous dispersions of phospholipids. |
| doi_str_mv | 10.1080/10426509208034501 |
| format | Article |
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The thermotropic phase transitions of these arsonolipids are characterized. Results show that the transition temperatures and enthalpies of fusion of the racemates are lower than those of the enantiomers in the powder form presumably because of conglomerate formation. The thermotropic transition characteristics of the aqueous dispersions of the arsonolipids change with the acyl chain lengths, and the overall behaviour is similar to that of the aqueous dispersions of phospholipids.</description><identifier>ISSN: 1042-6507</identifier><identifier>EISSN: 1563-5325</identifier><identifier>DOI: 10.1080/10426509208034501</identifier><identifier>CODEN: PSSLEC</identifier><language>eng</language><publisher>Philadelphia, PA: Taylor & Francis Group</publisher><subject>acylation ; Chemistry ; conglomerates ; decomposition ; Exact sciences and technology ; Lipids ; Optically active arsonic acids ; optically active arsonolipids ; Organic chemistry ; Preparations and properties ; thermotropic phase transitions</subject><ispartof>Phosphorus, sulfur, and silicon and the related elements, 1992-10, Vol.71 (1-4), p.99-105</ispartof><rights>Copyright Taylor & Francis Group, LLC 1992</rights><rights>1993 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c257t-e81fde75d442bf54a7c5825d083110b2b22cab5f4c7eea4eddfd03f95bdb4f803</citedby><cites>FETCH-LOGICAL-c257t-e81fde75d442bf54a7c5825d083110b2b22cab5f4c7eea4eddfd03f95bdb4f803</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.tandfonline.com/doi/pdf/10.1080/10426509208034501$$EPDF$$P50$$Ginformaworld$$H</linktopdf><linktohtml>$$Uhttps://www.tandfonline.com/doi/full/10.1080/10426509208034501$$EHTML$$P50$$Ginformaworld$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,59647,60436</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=4477433$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Serves, Spyros V.</creatorcontrib><creatorcontrib>Tsivgoulis, Gerasimos M.</creatorcontrib><creatorcontrib>Sotiropoulos, Demetrios N.</creatorcontrib><creatorcontrib>Ioannou, Panayiotis V.</creatorcontrib><creatorcontrib>Jain, Mahendra K.</creatorcontrib><title>SYNTHESIS OF (R)- AND (S)-1,2-DIACYLOXYPROPYL-3-ARSONIC ACIDS: OPTICALLY ACTIVE ARSONOLIPIDS</title><title>Phosphorus, sulfur, and silicon and the related elements</title><description>Reaction of trisodium arsenite with (R)- and (S)-glycidol affords in good yields the (R)- and (S)-1,2-dihydroxypropyl-3-arsonic acid, the tetrabutylammonium salt of which upon acylation with myristic, palmitic and stearic anhydrides in the presence of pyridine gives, in moderate to low yields, optically active arsonolipids, i.e., (R)- and (S)-1,2-diacyloxypropyl-3-arsonic acids. The thermotropic phase transitions of these arsonolipids are characterized. Results show that the transition temperatures and enthalpies of fusion of the racemates are lower than those of the enantiomers in the powder form presumably because of conglomerate formation. The thermotropic transition characteristics of the aqueous dispersions of the arsonolipids change with the acyl chain lengths, and the overall behaviour is similar to that of the aqueous dispersions of phospholipids.</description><subject>acylation</subject><subject>Chemistry</subject><subject>conglomerates</subject><subject>decomposition</subject><subject>Exact sciences and technology</subject><subject>Lipids</subject><subject>Optically active arsonic acids</subject><subject>optically active arsonolipids</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>thermotropic phase transitions</subject><issn>1042-6507</issn><issn>1563-5325</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1992</creationdate><recordtype>article</recordtype><recordid>eNp1kE1Lw0AQhhdRsFZ_gLccPLTg6n42qXgJaWsDoRuaKAaEsMlmoZI2Zbcg_fdurXoRT_Pxvs8MMwBcY3SHUYDuMWJkxNGYuIIyjvAJ6GE-opBTwk9d7nToDP45uLD2HSFnpagH3rJikc-nWZx5YuYNlkPohYuJN8iGEN8SOInDqEjEa5EuRVokkMJwmYlFHHlhFE-yB0-keRyFSVK4Rh6_TL0vXSRx6uRLcKZla5ur79gHz7NpHs1hIp4OFKwJ93ewCbBWjc8VY6TSnEm_5gHhCgUUY1SRipBaVlyz2m8ayRqltEJUj3mlKqbdvX2Aj3Nr01lrGl1uzWotzb7EqDy8p_zzHsfcHJmttLVstZGbemV_QcZ8n1HqbI9H22qjO7OWH51pVbmT-7YzPwz9f8snlVBu3g</recordid><startdate>19921001</startdate><enddate>19921001</enddate><creator>Serves, Spyros V.</creator><creator>Tsivgoulis, Gerasimos M.</creator><creator>Sotiropoulos, Demetrios N.</creator><creator>Ioannou, Panayiotis V.</creator><creator>Jain, Mahendra K.</creator><general>Taylor & Francis Group</general><general>Taylor and Francis</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19921001</creationdate><title>SYNTHESIS OF (R)- AND (S)-1,2-DIACYLOXYPROPYL-3-ARSONIC ACIDS: OPTICALLY ACTIVE ARSONOLIPIDS</title><author>Serves, Spyros V. ; Tsivgoulis, Gerasimos M. ; Sotiropoulos, Demetrios N. ; Ioannou, Panayiotis V. ; Jain, Mahendra K.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c257t-e81fde75d442bf54a7c5825d083110b2b22cab5f4c7eea4eddfd03f95bdb4f803</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1992</creationdate><topic>acylation</topic><topic>Chemistry</topic><topic>conglomerates</topic><topic>decomposition</topic><topic>Exact sciences and technology</topic><topic>Lipids</topic><topic>Optically active arsonic acids</topic><topic>optically active arsonolipids</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>thermotropic phase transitions</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Serves, Spyros V.</creatorcontrib><creatorcontrib>Tsivgoulis, Gerasimos M.</creatorcontrib><creatorcontrib>Sotiropoulos, Demetrios N.</creatorcontrib><creatorcontrib>Ioannou, Panayiotis V.</creatorcontrib><creatorcontrib>Jain, Mahendra K.</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Phosphorus, sulfur, and silicon and the related elements</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Serves, Spyros V.</au><au>Tsivgoulis, Gerasimos M.</au><au>Sotiropoulos, Demetrios N.</au><au>Ioannou, Panayiotis V.</au><au>Jain, Mahendra K.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>SYNTHESIS OF (R)- AND (S)-1,2-DIACYLOXYPROPYL-3-ARSONIC ACIDS: OPTICALLY ACTIVE ARSONOLIPIDS</atitle><jtitle>Phosphorus, sulfur, and silicon and the related elements</jtitle><date>1992-10-01</date><risdate>1992</risdate><volume>71</volume><issue>1-4</issue><spage>99</spage><epage>105</epage><pages>99-105</pages><issn>1042-6507</issn><eissn>1563-5325</eissn><coden>PSSLEC</coden><abstract>Reaction of trisodium arsenite with (R)- and (S)-glycidol affords in good yields the (R)- and (S)-1,2-dihydroxypropyl-3-arsonic acid, the tetrabutylammonium salt of which upon acylation with myristic, palmitic and stearic anhydrides in the presence of pyridine gives, in moderate to low yields, optically active arsonolipids, i.e., (R)- and (S)-1,2-diacyloxypropyl-3-arsonic acids. The thermotropic phase transitions of these arsonolipids are characterized. Results show that the transition temperatures and enthalpies of fusion of the racemates are lower than those of the enantiomers in the powder form presumably because of conglomerate formation. The thermotropic transition characteristics of the aqueous dispersions of the arsonolipids change with the acyl chain lengths, and the overall behaviour is similar to that of the aqueous dispersions of phospholipids.</abstract><cop>Philadelphia, PA</cop><pub>Taylor & Francis Group</pub><doi>10.1080/10426509208034501</doi><tpages>7</tpages></addata></record> |
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| identifier | ISSN: 1042-6507 |
| ispartof | Phosphorus, sulfur, and silicon and the related elements, 1992-10, Vol.71 (1-4), p.99-105 |
| issn | 1042-6507 1563-5325 |
| language | eng |
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| source | Taylor & Francis:Master (3349 titles) |
| subjects | acylation Chemistry conglomerates decomposition Exact sciences and technology Lipids Optically active arsonic acids optically active arsonolipids Organic chemistry Preparations and properties thermotropic phase transitions |
| title | SYNTHESIS OF (R)- AND (S)-1,2-DIACYLOXYPROPYL-3-ARSONIC ACIDS: OPTICALLY ACTIVE ARSONOLIPIDS |
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