Altenuene
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| Category | Mycotoxins |
| Catalog number | BBF-04104 |
| CAS | 29752-43-0 |
| Molecular Weight | 292.29 |
| Molecular Formula | C15H16O6 |
| Purity | >95% |
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Description
(-)-Altenuene is a toxin isolated from the fungus Alternaria tenuis. It has antioxidant activity and inhibits cholinesterases.
Specification
| Related CAS | 29752-43-0 |
| Synonyms | (2R,3R,4aR)-2,3,4,4a-Tetrahydro-2,3,7-trihydroxy-9-methoxy-4a-methyl-6H-dibenzo[b,d]pyran-6-one |
| Storage | Store at -20°C |
| IUPAC Name | (2R,3R,4aR)-2,3,7-trihydroxy-9-methoxy-4a-methyl-3,4-dihydro-2H-benzo[c]chromen-6-one |
| Canonical SMILES | CC12CC(C(C=C1C3=CC(=CC(=C3C(=O)O2)O)OC)O)O |
| InChI | InChI=1S/C15H16O6/c1-15-6-12(18)10(16)5-9(15)8-3-7(20-2)4-11(17)13(8)14(19)21-15/h3-5,10,12,16-18H,6H2,1-2H3/t10-,12-,15-/m1/s1 |
| InChI Key | MMHTXEATDNFMMY-WBIUFABUSA-N |
| Source | From Alternaria sp. |
Properties
| Appearance | Solid Powder |
| Boiling Point | 609.4±55.0°C at 760 mmHg |
| Melting Point | 158-161°C |
| Density | 1.5±0.1 g/cm3 |
| Solubility | Soluble in Acetone |
Reference Reading
1. Synthesis of Altenuene Backbones through Iodine(III)-Participated Umpolung Diesterification and Insights into the General [1,5]-H Shift in para-Dearomatization of Phenols via Quantum Chemical Calculations
Dan Luo, Liangzhen Hu, Tianyong Gao, Xiaohui Zhang, Yan Xiong J Org Chem. 2022 Apr 15;87(8):5065-5075. doi: 10.1021/acs.joc.1c02915. Epub 2022 Apr 4.
Through PhI(OAc)2-oxidized dearomatization and diesterification of 3'-hydroxy-[1,1'-biphenyl]-2-carboxylic acids, a series of polycyclic compounds possessing an altenuene backbone were obtained in moderate to good yields. The Umpolung diesterification reaction was completed under mild reaction conditions without an additional nucleophilic reagent. This work offers a concise method for the synthesis of diverse natural altenuene analogues. The mechanism was proposed, and the [1,5]-H shift was studied in isomerization from the ketone-form structure to a phenol employing computational studies.
2. Critical Assessment of Mycotoxins in Beverages and Their Control Measures
Md Shofiul Azam, Shafi Ahmed, Md Nahidul Islam, Pulak Maitra, Md Mahmudul Islam, Dianzhen Yu Toxins (Basel). 2021 Apr 30;13(5):323. doi: 10.3390/toxins13050323.
Mycotoxins are secondary metabolites of filamentous fungi that contaminate food products such as fruits, vegetables, cereals, beverages, and other agricultural commodities. Their occurrence in the food chain, especially in beverages, can pose a serious risk to human health, due to their toxicity, even at low concentrations. Mycotoxins, such as aflatoxins (AFs), ochratoxin A (OTA), patulin (PAT), fumonisins (FBs), trichothecenes (TCs), zearalenone (ZEN), and the alternaria toxins including alternariol, altenuene, and alternariol methyl ether have largely been identified in fruits and their derived products, such as beverages and drinks. The presence of mycotoxins in beverages is of high concern in some cases due to their levels being higher than the limits set by regulations. This review aims to summarize the toxicity of the major mycotoxins that occur in beverages, the methods available for their detection and quantification, and the strategies for their control. In addition, some novel techniques for controlling mycotoxins in the postharvest stage are highlighted.
3. First Synthesis of (-)-Altenuene-D3 Suitable as Internal Standard for Isotope Dilution Mass Spectrometry
Michael A Sebald, Julian Gebauer, Thomas Sommerfeld, Matthias Koch Molecules. 2019 Dec 12;24(24):4563. doi: 10.3390/molecules24244563.
Metabolites from Alternaria fungi exhibit a variety of biological properties such as phytotoxic, cytotoxic, or antimicrobial activity. Optimization of a literature procedure culminated in an efficient total synthesis of (-)-altenuene as well as a stable isotope-labeled derivative suitable for implementation in a LC-MS/MS method for mycotoxin analysis.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
