Synthesis of New A-Seco-Derivatives of Methyl Glycyrrhetinate
New A-seco-derivatives of methyl glycyrrhetinate (MeGLC) were synthesized. Cleavage of ring A of the 2-hydroxymethylene-3-oxo-derivative of MeGLC by H 2 O 2 (30%) in the presence of NaOMe (28%) in MeOH led to the 2,3-seco-2,3-diacid, which was isolated as the dimethyl ester. Ozonolysis of the 2-hydr...
Gespeichert in:
| Veröffentlicht in: | Chemistry of natural compounds 2024-07, Vol.60 (4), p.657-661 |
|---|---|
| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 661 |
|---|---|
| container_issue | 4 |
| container_start_page | 657 |
| container_title | Chemistry of natural compounds |
| container_volume | 60 |
| creator | Karimova, E. R. Baltina, L. A. Nugumanov, T. R. Medvedeva, N. I. Spirikhin, L. V. Kukovinets, O. S. |
| description | New A-seco-derivatives of methyl glycyrrhetinate (MeGLC) were synthesized. Cleavage of ring A of the 2-hydroxymethylene-3-oxo-derivative of MeGLC by H
2
O
2
(30%) in the presence of NaOMe (28%) in MeOH led to the 2,3-seco-2,3-diacid, which was isolated as the dimethyl ester. Ozonolysis of the 2-hydroxymethylene-3-oxo-derivative of MeGLC produced for the first time the methyl esters of 2,3-seco-2-ethoxycarbonyl- 18
βH
-olean-12-ene-2,3,30-trioic acid and 2,3-anhydro-11-oxo-18
βH
-olean-9,12-diene-2,3,30-trioic acid. |
| doi_str_mv | 10.1007/s10600-024-04407-2 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_3153773285</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3153773285</sourcerecordid><originalsourceid>FETCH-LOGICAL-c233t-ba6b3aff10acdf3f7a12f9071efb75a8b3a781a5cc34d2208e76729e3a4414273</originalsourceid><addsrcrecordid>eNp9kLFOwzAQhi0EEqXwAkyVWFgMZ18SOwNDVaAgFRgKs-WmZ5oqTYqdFuXtMS0SEgPT6XTf_-v0MXYu4EoAqOsgIAPgIBMOSQKKywPWE6lCrlHrQ9YDgJyjQDhmJyEs46qzTPfYzbSr2wWFMgwaN3imz8GQT6lo-C35cmvbcku7yxO1i64ajKuu6LxfUFvWtqVTduRsFejsZ_bZ2_3d6-iBT17Gj6PhhBcSseUzm83QOifAFnOHTlkhXQ5KkJup1Op4VFrYtCgwmUsJmlSmZE5ok0QkUmGfXe5717752FBozaoMBVWVranZBIMiRaVQ6jSiF3_QZbPxdfzOIOQ6UhnmkZJ7qvBNCJ6cWftyZX1nBJhvo2Zv1ESjZmfUyBjCfShEuH4n_1v9T-oLw_R3gg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>3098773639</pqid></control><display><type>article</type><title>Synthesis of New A-Seco-Derivatives of Methyl Glycyrrhetinate</title><source>Springer Online Journals</source><creator>Karimova, E. R. ; Baltina, L. A. ; Nugumanov, T. R. ; Medvedeva, N. I. ; Spirikhin, L. V. ; Kukovinets, O. S.</creator><creatorcontrib>Karimova, E. R. ; Baltina, L. A. ; Nugumanov, T. R. ; Medvedeva, N. I. ; Spirikhin, L. V. ; Kukovinets, O. S.</creatorcontrib><description>New A-seco-derivatives of methyl glycyrrhetinate (MeGLC) were synthesized. Cleavage of ring A of the 2-hydroxymethylene-3-oxo-derivative of MeGLC by H
2
O
2
(30%) in the presence of NaOMe (28%) in MeOH led to the 2,3-seco-2,3-diacid, which was isolated as the dimethyl ester. Ozonolysis of the 2-hydroxymethylene-3-oxo-derivative of MeGLC produced for the first time the methyl esters of 2,3-seco-2-ethoxycarbonyl- 18
βH
-olean-12-ene-2,3,30-trioic acid and 2,3-anhydro-11-oxo-18
βH
-olean-9,12-diene-2,3,30-trioic acid.</description><identifier>ISSN: 0009-3130</identifier><identifier>EISSN: 1573-8388</identifier><identifier>DOI: 10.1007/s10600-024-04407-2</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>acids ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Esters ; Hydrogen peroxide ; Organic Chemistry ; ozonolysis ; Plant Sciences</subject><ispartof>Chemistry of natural compounds, 2024-07, Vol.60 (4), p.657-661</ispartof><rights>Springer Science+Business Media, LLC, part of Springer Nature 2024. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c233t-ba6b3aff10acdf3f7a12f9071efb75a8b3a781a5cc34d2208e76729e3a4414273</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s10600-024-04407-2$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s10600-024-04407-2$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27903,27904,41467,42536,51297</link.rule.ids></links><search><creatorcontrib>Karimova, E. R.</creatorcontrib><creatorcontrib>Baltina, L. A.</creatorcontrib><creatorcontrib>Nugumanov, T. R.</creatorcontrib><creatorcontrib>Medvedeva, N. I.</creatorcontrib><creatorcontrib>Spirikhin, L. V.</creatorcontrib><creatorcontrib>Kukovinets, O. S.</creatorcontrib><title>Synthesis of New A-Seco-Derivatives of Methyl Glycyrrhetinate</title><title>Chemistry of natural compounds</title><addtitle>Chem Nat Compd</addtitle><description>New A-seco-derivatives of methyl glycyrrhetinate (MeGLC) were synthesized. Cleavage of ring A of the 2-hydroxymethylene-3-oxo-derivative of MeGLC by H
2
O
2
(30%) in the presence of NaOMe (28%) in MeOH led to the 2,3-seco-2,3-diacid, which was isolated as the dimethyl ester. Ozonolysis of the 2-hydroxymethylene-3-oxo-derivative of MeGLC produced for the first time the methyl esters of 2,3-seco-2-ethoxycarbonyl- 18
βH
-olean-12-ene-2,3,30-trioic acid and 2,3-anhydro-11-oxo-18
βH
-olean-9,12-diene-2,3,30-trioic acid.</description><subject>acids</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Esters</subject><subject>Hydrogen peroxide</subject><subject>Organic Chemistry</subject><subject>ozonolysis</subject><subject>Plant Sciences</subject><issn>0009-3130</issn><issn>1573-8388</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp9kLFOwzAQhi0EEqXwAkyVWFgMZ18SOwNDVaAgFRgKs-WmZ5oqTYqdFuXtMS0SEgPT6XTf_-v0MXYu4EoAqOsgIAPgIBMOSQKKywPWE6lCrlHrQ9YDgJyjQDhmJyEs46qzTPfYzbSr2wWFMgwaN3imz8GQT6lo-C35cmvbcku7yxO1i64ajKuu6LxfUFvWtqVTduRsFejsZ_bZ2_3d6-iBT17Gj6PhhBcSseUzm83QOifAFnOHTlkhXQ5KkJup1Op4VFrYtCgwmUsJmlSmZE5ok0QkUmGfXe5717752FBozaoMBVWVranZBIMiRaVQ6jSiF3_QZbPxdfzOIOQ6UhnmkZJ7qvBNCJ6cWftyZX1nBJhvo2Zv1ESjZmfUyBjCfShEuH4n_1v9T-oLw_R3gg</recordid><startdate>20240701</startdate><enddate>20240701</enddate><creator>Karimova, E. R.</creator><creator>Baltina, L. A.</creator><creator>Nugumanov, T. R.</creator><creator>Medvedeva, N. I.</creator><creator>Spirikhin, L. V.</creator><creator>Kukovinets, O. S.</creator><general>Springer US</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7S9</scope><scope>L.6</scope></search><sort><creationdate>20240701</creationdate><title>Synthesis of New A-Seco-Derivatives of Methyl Glycyrrhetinate</title><author>Karimova, E. R. ; Baltina, L. A. ; Nugumanov, T. R. ; Medvedeva, N. I. ; Spirikhin, L. V. ; Kukovinets, O. S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c233t-ba6b3aff10acdf3f7a12f9071efb75a8b3a781a5cc34d2208e76729e3a4414273</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>acids</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Esters</topic><topic>Hydrogen peroxide</topic><topic>Organic Chemistry</topic><topic>ozonolysis</topic><topic>Plant Sciences</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Karimova, E. R.</creatorcontrib><creatorcontrib>Baltina, L. A.</creatorcontrib><creatorcontrib>Nugumanov, T. R.</creatorcontrib><creatorcontrib>Medvedeva, N. I.</creatorcontrib><creatorcontrib>Spirikhin, L. V.</creatorcontrib><creatorcontrib>Kukovinets, O. S.</creatorcontrib><collection>CrossRef</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Chemistry of natural compounds</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Karimova, E. R.</au><au>Baltina, L. A.</au><au>Nugumanov, T. R.</au><au>Medvedeva, N. I.</au><au>Spirikhin, L. V.</au><au>Kukovinets, O. S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of New A-Seco-Derivatives of Methyl Glycyrrhetinate</atitle><jtitle>Chemistry of natural compounds</jtitle><stitle>Chem Nat Compd</stitle><date>2024-07-01</date><risdate>2024</risdate><volume>60</volume><issue>4</issue><spage>657</spage><epage>661</epage><pages>657-661</pages><issn>0009-3130</issn><eissn>1573-8388</eissn><abstract>New A-seco-derivatives of methyl glycyrrhetinate (MeGLC) were synthesized. Cleavage of ring A of the 2-hydroxymethylene-3-oxo-derivative of MeGLC by H
2
O
2
(30%) in the presence of NaOMe (28%) in MeOH led to the 2,3-seco-2,3-diacid, which was isolated as the dimethyl ester. Ozonolysis of the 2-hydroxymethylene-3-oxo-derivative of MeGLC produced for the first time the methyl esters of 2,3-seco-2-ethoxycarbonyl- 18
βH
-olean-12-ene-2,3,30-trioic acid and 2,3-anhydro-11-oxo-18
βH
-olean-9,12-diene-2,3,30-trioic acid.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s10600-024-04407-2</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0009-3130 |
| ispartof | Chemistry of natural compounds, 2024-07, Vol.60 (4), p.657-661 |
| issn | 0009-3130 1573-8388 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_3153773285 |
| source | Springer Online Journals |
| subjects | acids Chemistry Chemistry and Materials Science Chemistry/Food Science Esters Hydrogen peroxide Organic Chemistry ozonolysis Plant Sciences |
| title | Synthesis of New A-Seco-Derivatives of Methyl Glycyrrhetinate |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-27T20%3A24%3A25IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20New%20A-Seco-Derivatives%20of%20Methyl%20Glycyrrhetinate&rft.jtitle=Chemistry%20of%20natural%20compounds&rft.au=Karimova,%20E.%20R.&rft.date=2024-07-01&rft.volume=60&rft.issue=4&rft.spage=657&rft.epage=661&rft.pages=657-661&rft.issn=0009-3130&rft.eissn=1573-8388&rft_id=info:doi/10.1007/s10600-024-04407-2&rft_dat=%3Cproquest_cross%3E3153773285%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=3098773639&rft_id=info:pmid/&rfr_iscdi=true |