| Revision as of 23:36, 3 January 2025 editInnerstream (talk | contribs)Autopatrolled, Extended confirmed users4,071 edits new page | Latest revision as of 22:00, 7 January 2025 edit undoGraeme Bartlett (talk | contribs)Administrators249,755 edits more ids | ||
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| | Section1 = {{Chembox Identifiers | | Section1 = {{Chembox Identifiers | ||
| | CASNo = 522-53-2 | | CASNo = 522-53-2 | ||
| | ChEBI = 93548 | |||
| | ChEMBL = 551842 | |||
| | ChemSpiderID = 65927 | |||
| | PubChem = 73157 | | PubChem = 73157 | ||
| | SMILES = CCCCCC1=C(C(=CC2=C1OC3=CC(=CC(=C3C(=O)O2)C(=O)CCCC)OC)O)C(=O)O | | SMILES = CCCCCC1=C(C(=CC2=C1OC3=CC(=CC(=C3C(=O)O2)C(=O)CCCC)OC)O)C(=O)O | ||
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| | Density = | | Density = | ||
| | MeltingPtC = 196-198 | | MeltingPtC = 196-198 | ||
| | MeltingPt_ref = <ref>{{cite journal | doi = 10.1016/j.bmcl.2009.03.170 | title = Antimitotic activity of lobaric acid and a new benzofuran, sakisacaulon a from Stereocaulon sasakii | date = 2009 | last1 = Morita | first1 = Hiroshi | last2 = Tsuchiya | first2 = Tomoe | last3 = Kishibe | first3 = Koji | last4 = Noya | first4 = Sayaka | last5 = Shiro | first5 = Motoo | last6 = Hirasawa | first6 = Yusuke | journal = Bioorganic & Medicinal Chemistry Letters | volume = 19 | issue = 13 | pages = 3679–3681 | pmid = 19481447 }}</ref> | |||
| | MeltingPt_ref = <ref>{{cite journal | doi = 10.1016/j.bmcl.2009.03.170 }}</ref> | |||
| | BoilingPt = | | BoilingPt = | ||
| | Solubility = | | Solubility = | ||
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| }} | }} | ||
| '''Lobaric acid''' is a chemical compound with the molecular formula {{chem2|C25H28O8}}. It has been found in the Antarctic ] '']''<ref>{{Cite journal | doi = 10.3390/md15030028 }}</ref> and a variety of other lichens. It is a member of the ] class of compounds. | '''Lobaric acid''' is a chemical compound with the molecular formula {{chem2|C25H28O8}}. It has been found in the Antarctic ] '']''<ref>{{Cite journal | doi = 10.3390/md15030028 | doi-access = free | title = Secondary Metabolites from Polar Organisms | date = 2017 | last1 = Tian | first1 = Yuan | last2 = Li | first2 = Yan-Ling | last3 = Zhao | first3 = Feng-Chun | journal = Marine Drugs | volume = 15 | issue = 3 | page = 28 | pmid = 28241505 | pmc = 5367009 }}</ref> and a variety of other lichens. It is a member of the ] class of compounds. | ||
| The first ] of lobaric acid was reported in 2018 by researchers at the ] and ]. The synthesis was accomplished in 14 total steps, starting with 4-bromophthalic anhydride. Key steps included an ] to connect the two main ]s, followed by a seven-membered lactonization reaction to form the final structure. The synthetic route also allowed access to several derivatives of lobaric acid, including methyllobarin, lobarin, and lobarstin, which showed significant ] 1B (]) ] activities.<ref>{{Cite journal | doi = 10.1021/acs.jnatprod.8b00227 | title = Total Syntheses of Lobaric Acid and Its Derivatives from the Antarctic Lichen ''Stereocaulon alpinum'' | date = 2018 | last1 = Kim | first1 = Tai Kyoung | last2 = Kim | first2 = Joung Eun | last3 = Youn | first3 = Ui Joung | last4 = Han | first4 = Se Jong | last5 = Kim | first5 = Il-Chan | last6 = Cho | first6 = Cheon-Gyu | last7 = Yim | first7 = Joung Han | journal = Journal of Natural Products | volume = 81 | issue = 6 | pages = 1460–1467 | pmid = 29878768 }}</ref> | |||
| A laboratory synthesis of lobaric acid has been reported.<ref>{{Cite journal | doi = 110.1021/acs.jnatprod.8b00227 }}</ref> | |||
| ==References== | ==References== | ||
| {{reflist}} | {{reflist}} | ||
| {{organic-compound-stub}} | |||
| ] | ] | ||
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| ] | ] | ||
| ] | ] | ||
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Latest revision as of 22:00, 7 January 2025
| |
| Names | |
|---|---|
| IUPAC name 3-Hydroxy-9-methoxy-6-oxo-7-pentanoyl-1-pentylbenzobenzodioxepine-2-carboxylic acid | |
| Other names Lobraric acid; stereocaulic acid | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| PubChem CID | |
| CompTox Dashboard (EPA) | |
InChI
| |
SMILES
| |
| Properties | |
| Chemical formula | C25H28O8 |
| Molar mass | 456.491 g·mol |
| Melting point | 196–198 °C (385–388 °F; 469–471 K) |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references | |
Lobaric acid is a chemical compound with the molecular formula C25H28O8. It has been found in the Antarctic lichen Stereocaulon alpinum and a variety of other lichens. It is a member of the depsidone class of compounds.
The first total synthesis of lobaric acid was reported in 2018 by researchers at the Korea Polar Research Institute and Hanyang University. The synthesis was accomplished in 14 total steps, starting with 4-bromophthalic anhydride. Key steps included an Ullmann aryl ether coupling reaction to connect the two main aromatic rings, followed by a seven-membered lactonization reaction to form the final structure. The synthetic route also allowed access to several derivatives of lobaric acid, including methyllobarin, lobarin, and lobarstin, which showed significant protein tyrosine phosphatase 1B (PTP1B) inhibitory activities.
References
- Morita, Hiroshi; Tsuchiya, Tomoe; Kishibe, Koji; Noya, Sayaka; Shiro, Motoo; Hirasawa, Yusuke (2009). "Antimitotic activity of lobaric acid and a new benzofuran, sakisacaulon a from Stereocaulon sasakii". Bioorganic & Medicinal Chemistry Letters. 19 (13): 3679–3681. doi:10.1016/j.bmcl.2009.03.170. PMID 19481447.
- Tian, Yuan; Li, Yan-Ling; Zhao, Feng-Chun (2017). "Secondary Metabolites from Polar Organisms". Marine Drugs. 15 (3): 28. doi:10.3390/md15030028. PMC 5367009. PMID 28241505.
- Kim, Tai Kyoung; Kim, Joung Eun; Youn, Ui Joung; Han, Se Jong; Kim, Il-Chan; Cho, Cheon-Gyu; Yim, Joung Han (2018). "Total Syntheses of Lobaric Acid and Its Derivatives from the Antarctic Lichen Stereocaulon alpinum". Journal of Natural Products. 81 (6): 1460–1467. doi:10.1021/acs.jnatprod.8b00227. PMID 29878768.