Stachybotrin C
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| Category | Antibiotics |
| Catalog number | BBF-02955 |
| CAS | 150351-23-8 |
| Molecular Weight | 505.64 |
| Molecular Formula | C31H39NO5 |
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Description
It is a neuritogenic agent produced by the strain of Stachyborrys parvispora F4708. It promotes the enlargement of the neural sinus of P12 cells, and the effect of Stachybotrin C is obvious, but the effect of Parvisporin is weak.
Specification
| Synonyms | Pyrano[2,3-e]isoindol-7(2H)-one, 2-[(3E)-4,8-dimethyl-3,7-nonadien-1-yl]-3,4,8,9-tetrahydro-3,5-dihydroxy-8-[2-(4-hydroxyphenyl)ethyl]-2-methyl-, (2R,3R)-rel-; Pyrano[2,3-e]isoindol-7(2H)-one, 2-(4,8-dimethyl-3,7-nonadienyl)-3,4,8,9-tetrahydro-3,5-dihydroxy-8-[2-(4-hydroxyphenyl)ethyl]-2-methyl-, [2a(E),3a]-; Antibiotic NG 245 |
| IUPAC Name | (2R,3R)-2-[(3E)-4,8-dimethylnona-3,7-dienyl]-3,5-dihydroxy-8-[2-(4-hydroxyphenyl)ethyl]-2-methyl-4,9-dihydro-3H-pyrano[2,3-e]isoindol-7-one |
| Canonical SMILES | CC(=CCCC(=CCCC1(C(CC2=C(C=C3C(=C2O1)CN(C3=O)CCC4=CC=C(C=C4)O)O)O)C)C)C |
| InChI | InChI=1S/C31H39NO5/c1-20(2)7-5-8-21(3)9-6-15-31(4)28(35)18-25-27(34)17-24-26(29(25)37-31)19-32(30(24)36)16-14-22-10-12-23(33)13-11-22/h7,9-13,17,28,33-35H,5-6,8,14-16,18-19H2,1-4H3/b21-9+/t28-,31-/m1/s1 |
| InChI Key | VXPNPWUFHMIFJE-LCVDRPHOSA-N |
Properties
| Appearance | Pale Yellow to White Powder |
| Melting Point | 89-92°C |
| Solubility | Soluble in Methanol |
Reference Reading
1. Synthesis of stachybotrin C and all of its stereoisomers: structure revision
Maiwenn Jacolot, Mickael Jean, Naresh Tumma, Arnaud Bondon, Srivari Chandrasekhar, Pierre van de Weghe J Org Chem. 2013 Jul 19;78(14):7169-75. doi: 10.1021/jo401116r. Epub 2013 Jun 28.
We disclose the first total synthesis of stachybotrin C, a potent neuroprotective natural compound. All of the four stereoisomers have been prepared and fully characterized with the aim to attribute the absolute configuration of the two adjacent stereocenters of the stachybotrin C.
2. Confirmation of the absolute configuration of Stachybotrin C using single-crystal X-ray diffraction analysis of its 4-bromobenzyl ether derivative
Yu Kuroda, Keiko Hasegawa, Keiichi Noguchi, Kazuhiro Chiba, Keiji Hasumi, Yoshikazu Kitano J Antibiot (Tokyo). 2018 Jun;71(6):584-591. doi: 10.1038/s41429-018-0042-2. Epub 2018 Mar 19.
The absolute configuration of Stachybotrin C was confirmed in this study. After synthesizing the dimethyl ethers of Stachybotrin C, the C-8 epimer was analyzed by 1D NOESY. However, the stereochemistry determination was difficult through the NOE correlations. Instead, the di(4-bromobenzyl) ether of Stachybotrin C was derived and used for X-ray diffraction analysis, because its single crystal was easier to obtain than that of the original Stachybotrin C. The stereochemistry of Stachybotrin C was determined to be (8S, 9R). This derivatization approach may also be used to prepare single crystals of the analogues.
3. Synthesis of tricyclic pyrano[2,3-e]isoindolin-3-ones as the core structure of stachybotrin A, B, and C
Seiichi Inoue, Riyoung Kim, Yujiro Hoshino, Kiyoshi Honda Chem Commun (Camb). 2006 May 14;(18):1974-6. doi: 10.1039/b601433j. Epub 2006 Apr 3.
The substituted tricyclic pyrano[2,3-e]isoindolin-3-ones and , as the core structure of stachybotrin A, B, and C (), have been regioselectively synthesized for the first time by a short route which involved Mannich reaction and Claisen rearrangement.
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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 ╳
