F1839-I
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Others |
| Catalog number | BBF-04384 |
| CAS | 159096-49-8 |
| Molecular Weight | 372.50 |
| Molecular Formula | C23H32O4 |
| Purity | ≥98% |
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Description
F1839-I is produced from Stachybotrys sp.
Specification
| Synonyms | Antibiotic F1839-I; (2R,2'R,4'aS,6'R,8'aS)-2',4-dihydroxy-1',1',4'a,6,6'-pentamethyl-spiro[3H-benzofuran-2,5'-decalin]-7-carbaldehyde; Spiro[benzofuran-2(3H),1'(2'H)-naphthalene]-7-carboxaldehyde, 3',4',4'a,5',6',7',8',8'a-octahydro-4,6'-dihydroxy-2',5',5',6,8'a-pentamethyl-, (1'R,2'R,4'aS,6R,8'aS)- |
| Storage | Store at 2-8°C protect from light |
| IUPAC Name | (3R,4aS,7R,8R,8aS)-3,4'-dihydroxy-4,4,6',7,8a-pentamethylspiro[2,3,4a,5,6,7-hexahydro-1H-naphthalene-8,2'-3H-1-benzofuran]-7'-carbaldehyde |
| Canonical SMILES | CC1CCC2C(C(CCC2(C13CC4=C(C=C(C(=C4O3)C=O)C)O)C)O)(C)C |
| InChI | InChI=1S/C23H32O4/c1-13-10-17(25)15-11-23(27-20(15)16(13)12-24)14(2)6-7-18-21(3,4)19(26)8-9-22(18,23)5/h10,12,14,18-19,25-26H,6-9,11H2,1-5H3/t14-,18+,19-,22+,23-/m1/s1 |
| InChI Key | UOIBNKXNAPXQNY-JEWZMFNGSA-N |
Properties
| Appearance | Amorphous Powder |
| Boiling Point | 523.6±50.0°C (Predicted) |
| Density | 1.19±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol |
Reference Reading
1. Discovery of Cymopolyphenols A-F From a Marine Mesophotic Zone Aaptos Sponge-Associated Fungus Cymostachys sp. NBUF082
Tingting Wang, Jing Zhou, Jiabin Zou, Yutong Shi, Wenli Zhou, Peng Shao, Tianze Yu, Wei Cui, Xiaohui Li, Xingxin Wu, Jing Ye, Xiaojun Yan, C Benjamin Naman, J Enrico H Lazaro, Shan He Front Microbiol. 2021 Feb 22;12:638610. doi: 10.3389/fmicb.2021.638610. eCollection 2021.
Mesophotic coral ecosystems (MCEs) have complex but understudied biodiversity, especially for natural products discovery. Untargeted metabolomics research on 80 extracts prepared from marine sponge-associated fungi, half from shallow reefs (<30 m) and half from MCEs (30-150 m), facilitated prioritization for further study a Cymostachys fungus from a 103 m deep Aaptos sponge. LC-MS target-directed isolation yielded a series of new compounds, cymopolyphenols A-F (1-6), and two known phenylspirodrimanes, F1839-I (7) and stachybotrylactone (8). This is the first report of natural products from the recently described genus, Cymostachys. Compounds 1-6 and 8 contain a dihydroisobenzofuran moiety, and 4-6 are low-order polymers of 1 with novel scaffolds. The structures of the compounds were established by spectroscopic and spectrometric data interpretation, with further support from X-ray crystallography studies of 3 and 4. Compound 3 undergoes facile racemization in solution and was found to crystalize as a racemic mixture. Compound 5 was also obtained in racemic form, and after chiral chromatography, both separated enantiomers racemized in solution by a presumed keto-enol tautomerization. Compounds 1 and 3-6 were found to be weakly antimicrobial (MIC 16-64 μg/ml) in vitro against several Gram-positive and Gram-negative human or aquatic pathogens, compound 5 was shown to chelate iron in vitro at 10 μM, and 8 activated plant disease resistance in vivo in a transgenic model organism.
2. Enantiospecific total syntheses of meroterpenoids (-)-F1839-I and (-)-corallidictyals B and D
Dattatraya H Dethe, Balu D Dherange, Saghir Ali, Mahesh M Parsutkar Org Biomol Chem. 2016 Dec 20;15(1):65-68. doi: 10.1039/c6ob02322c.
Enantiospecific total syntheses of spiromeroterpenoid natural products (-)-F1839-I and (-)-corallidictyals B and D were achieved using the environmentally benign and highly atom economical Lewis acid catalysed Friedel-Crafts reaction and a highly regio- and stereoselective spirocyclic C-O bond formation reaction.
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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 ╳
