Pannarin
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| Category | Others |
| Catalog number | BBF-05453 |
| CAS | 55609-84-2 |
| Molecular Weight | 362.76 |
| Molecular Formula | C18H15ClO6 |
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Description
It is a lichen metabolite isolated from several Psoroma species.
Specification
| Synonyms | 8-chloro-9-hydroxy-3-methoxy-1,4,7-trimethyl-6-oxobenzo[b][1,4]benzodioxepine-10-carbaldehyde; Pannarine; NSC 646008; 11H-Dibenzo(b,e)(1,4)dioxepin-4-carboxaldehyde, 2-chloro-3-hydroxy-8-methoxy-1,6,9-trimethyl-11-oxo- |
| IUPAC Name | 2-chloro-3-hydroxy-8-methoxy-1,6,9-trimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepine-4-carbaldehyde |
| Canonical SMILES | CC1=CC(=C(C2=C1OC3=C(C(=C(C(=C3C(=O)O2)C)Cl)O)C=O)C)OC |
| InChI | InChI=1S/C18H15ClO6/c1-7-5-11(23-4)8(2)16-15(7)24-17-10(6-20)14(21)13(19)9(3)12(17)18(22)25-16/h5-6,21H,1-4H3 |
| InChI Key | LVGKNESDSKGROR-UHFFFAOYSA-N |
Properties
| Boiling Point | 563.8°C at 760 mmHg |
| Density | 1.41 g/cm3 |
Reference Reading
1. A radical shift in the taxonomy of Lepraria s.l.: molecular and morphological studies shed new light on the evolution of asexuality and lichen growth form diversification
James C Lendemer, Brendan P Hodkinson Mycologia. 2013 Jul-Aug;105(4):994-1018. doi: 10.3852/12-338. Epub 2013 May 26.
A combination of molecular phylogenetic analyses of ITS and mtSSU sequences, morphological and chemical analyses were used to investigate the lineages nominally included in the sterile lichen genus Lepraria. A core group (Lepraria s. str.) was resolved as sister to Stereocaulon. Species producing the secondary compounds argopsin, pannarin and usnic acid were found to belong to other lineages of lichen-forming ascomycetes. Study of Leprocaulon revealed that all species, except the type, likely represent members of Lepraria s. str. that have evolved a fruticose growth form. The correct name for the type species of Leprocaulon is shown to be L. quisquiliare, not L. microscopicum, and the genus is redefined to include several species previously placed in Lepraria. Leprocaulon quisquiliare is also shown to comprise two morphologically convergent species. The name is lectotypified and epitypified on material from the type region (Germany) and its application restricted to Old World populations. New World populations of L. quisquiliare are described as L. americanum. Leprocaulon, in its revised sense, is recognized in a new family (Leprocaulaceae) and order (Leprocaulales) sister to the Caliciales and including the genus Halecania. A new genus of Pilocarpaceae, Nelsenium, is introduced to accommodate Lepraria usnica. The status of Lepraria ecorticata is discussed in the context of usnic acid-producing Lecanora species. These nomenclatural novelties are proposed: (i) transfers from Leprocaulon to Lepraria: Lepraria albicans comb. nov., L. arbuscula comb. nov., L. congestum comb. nov., L. gracilescens comb. nov., L. pseudoarbuscula comb. nov., L. subalbicans comb. nov., L. tenellum comb. nov.; (ii) transfers from Lepraria to Leprocaulon: Leprocaulon adhaerens comb. nov., L. coriense, L. santamonicae comb. nov., L. terricola comb. nov. and L. textum comb. nov.; (iii) new taxa: Leprocaulales ord. nov., Leprocaulaceae fam. nov., Nelsenium gen. nov., Leprocaulon americanum sp. nov. and L. knudsenii sp. nov.
2. UV-protectant metabolites from lichens and their symbiotic partners
Khanh-Hung Nguyen, Marylène Chollet-Krugler, Nicolas Gouault, Sophie Tomasi Nat Prod Rep. 2013 Dec;30(12):1490-508. doi: 10.1039/c3np70064j.
Lichens are structurally complex symbiotic organisms that are exposed to a wide variety of external conditions (extreme temperatures, desiccation, UV radiation, etc.). These poikilohydric organisms have developed various mechanisms of photoprotection, such as light scattering, radiation screening, thermal dissipation, activation of antioxidant defense and macromolecules and membrane repair. These unique organisms produce a vast array of compounds, with more than 1000 secondary metabolites known. An important protective mechanism of lichens is the production of UV screening compounds, such as phenolic compounds (depsidones, depsides, diphenyl ethers), anthraquinones, xanthones or shikimic acid derivatives (calycin, mycosporines, scytonemin). Due to the harmful effects of the UVA wavelengths of sunlight, the search for new sunscreens remains important. We herein propose a review that focuses on the UV protectants from lichens and their symbiotic partners (lichenized fungi, green alga, cyanobacteria). In fact, lichens produce unique and/or efficient UV filters such as depsidones (lobaric acid, pannarin, etc.), depsides (atranorin, gyrophoric acid, etc.), diphenyl ethers (epiphorellic acids, buellin), bisxanthones (secalonic acids, etc.), mycosporines and MAAs, scytonemin along with classical pigments (melanin, carotenoids). We propose to classify these compounds with regard to their chemical structures and review the physicochemical properties that act as UV filters. While the most abundant lichen polyfunctionalized aromatic compounds, belonging to orsellinic derivatives, are UVB screens, these organisms produce strong UVA filters, e.g., calycin (pulvinic acid derivatives), bisxanthones (secalonic acids), scytonemin or mycosporines and MAAs with the latter ones exhibiting attractive properties as photoprotectants.
3. Two new Rinodina lichens from South Korea, with an updated key to the species of Rinodina in the far eastern Asia
Beeyoung Gun Lee, Jae-Seoun Hur MycoKeys. 2022 Feb 23;87:159-182. doi: 10.3897/mycokeys.87.71524. eCollection 2022.
Rinodinasalicis Lee & Hur and Rinodinazeorina Lee & Hur are described as new lichen-forming fungi from forested wetlands or a humid forest in South Korea. Rinodinasalicis is distinguishable from Rinodinaexcrescens Vain., the most similar species, by its olive-gray thallus with smaller areoles without having blastidia, contiguous apothecia, non-pruinose discs, paler disc color, wider ascospores in the Pachysporaria-type II, and the absence of secondary metabolites. Rinodinazeorina differs from Rinodinahypobadia Sheard by areolate and brownish thallus, non-pruinose apothecia, colorless and wider parathecium, narrower paraphyses with non-pigmented and unswollen tips, longer and narrower ascospores with angular to globose lumina, and the absence of pannarin. Molecular analyses employing internal transcribed spacer (ITS) sequences strongly support the two new species to be unique in the genus Rinodina. An updated key is provided to assist in the identification of all 63 taxa in Rinodina of the far eastern Asia.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
