trans-4-Hydroxymellein
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| Category | Others |
| Catalog number | BBF-05546 |
| CAS | 70287-70-6 |
| Molecular Weight | 194.18 |
| Molecular Formula | C10H10O4 |
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Description
It is produced by the strain of Apiospora camptospora and marine-derived Microsphaeropsis sp. H5-50. It is the constituent of Moringa oleifera (horseradish tree) and Septoria nodorum.
Specification
| Related CAS | 60132-20-9 ((3S,4S)-form) 32885-83-9 ((3R,4R)-form) |
| Synonyms | 1H-2-Benzopyran-1-one, 3,4-dihydro-4,8-dihydroxy-3-methyl-, (3R,4S)-; (3R,4S)-hydroxymellein; (3R,4S)-4,8-dihydroxy-3-methylisochroman-1-one; 1H-2-Benzopyran-1-one, 3,4-dihydro-4,8-dihydroxy-3-methyl-, (3R-trans)-; (-)-trans-4-hydroxymellein |
| IUPAC Name | (3R,4S)-4,8-dihydroxy-3-methyl-3,4-dihydroisochromen-1-one |
| Canonical SMILES | CC1C(C2=C(C(=CC=C2)O)C(=O)O1)O |
| InChI | InChI=1S/C10H10O4/c1-5-9(12)6-3-2-4-7(11)8(6)10(13)14-5/h2-5,9,11-12H,1H3/t5-,9-/m1/s1 |
| InChI Key | STSOHAOGZMLWFR-MLUIRONXSA-N |
Properties
| Appearance | Solid |
| Boiling Point | 427.2±45.0°C at 760 mmHg |
| Melting Point | 131-132°C |
| Density | 1.4±0.1 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Cytotoxic activity of fungal strains isolated from the ascidian Eudistoma vannamei
Tasso G C Montenegro, Felipe A R Rodrigues, Paula C Jimenez, Alysson L Angelim, Vânia M M Melo, Edson Rodrigues Filho, Maria da Conceição F de Oliveira, Letícia V Costa-Lotufo Chem Biodivers. 2012 Oct;9(10):2203-9. doi: 10.1002/cbdv.201100366.
The cytotoxic activity at 50 μg/ml of extracts obtained from eleven fungal strains associated to Eudistoma vannamei, an endemic ascidian from Northeast Brazil, against two cell lines, i.e., the HCT-8 (colon cancer) and the MDA-MB-435 (melanoma) cell lines, was investigated. The most promising extract (EV10) was obtained from a fungus identified as Aspergillus sp. by molecular analysis and was selected for bioassay-guided isolation of its active principals. Large-scale fermentation of EV10 in potato-dextrose broth followed by chromatographic purification of the active extract from the liquid medium allowed the isolation of the isocoumarins mellein, cis-4-hydroxymellein, and trans-4-hydroxymellein, besides penicillic acid. All isolated compounds were tested for their cytotoxicity against the tumor cell lines MDA-MB-435 and HCT-8 and revealed penicillic acid as the only cytotoxic compound (cell growth inhibitions >95%).
2. Two new antimicrobial metabolites from the endophytic fungus, Seimatosporium sp
Hidayat Hussain, Karsten Krohn, Barbara Schulz, Siegfried Draeger, Mamona Nazir, Muhammad Saleem Nat Prod Commun. 2012 Mar;7(3):293-4.
Two new acaranoic acids, named seimatoporic acid A and B (1, and 2), together with six known compounds, R-(-)-mellein (3), cis-4-hydroxymellein (4), trans-4-hydroxymellein (5), 4R-hydroxy-5-methylmellein (6), (-)-5-hydroxymethylmellein (7), and ergosterol (8) were isolated from an endophytic fungus, Seimatosporium sp, by a bioassay-guided procedure. The structures of the new compounds have been assigned from analysis of the 1H and 13C NMR spectra, DEPT, and by 2D COSY, HMQC, HMBC and NOESY experiments. A mixture of compounds 1 and 2 showed strong antifungal activity against Botrytis cinerea, Septoria tritici, and Pyricularia oryzae.
3. A new dihydrobenzofuran derivative from the endophytic fungus Botryosphaeria mamane PSU-M76
Wipapan Pongcharoen, Vatcharin Rukachaisirikul, Souwalak Phongpaichit, Jariya Sakayaroj Chem Pharm Bull (Tokyo). 2007 Sep;55(9):1404-5. doi: 10.1248/cpb.55.1404.
One new dihydrobenzofuran derivative, botryomaman (1), was isolated from the broth extract of the endophytic fungus Botryosphaeria mamane PSU-M76 along with six known compounds, 2,4-dimethoxy-6-pentylphenol, (R)-(-)-mellein, primin, cis-4-hydroxymellein, trans-4-hydroxymellein and 4,5-dihydroxy-2-hexenoic acid. The structures were assigned by spectroscopic methods. All compounds were tested for antibacterial activity against Staphylococcus aureus ATCC 25923 and methicillin-resistant S. aureus SK1. Primin showed the best activity against both strains with equal MIC values of 8 microg/ml.
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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 ╳
