Alliacol A
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| Category | Antibiotics |
| Catalog number | BBF-00421 |
| CAS | 79232-29-4 |
| Molecular Weight | 264.32 |
| Molecular Formula | C15H20O4 |
| Purity | 95% |
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Description
It is produced by the strain of Marasmium alliaceus. It has weak antibacterial and fungal activity and strong inhibition of DNA synthesis of Ehrlician ascites cancer cells (2-5 ㎍/mL). The reaction with cysteine to form an admixture greatly reduced the biological activity.
Specification
| Synonyms | DTXSID80229590; 8H-Oxireno[1,7a]indeno[3a,4-b]furan-6(2H)-one,hexahydro-4a-hydroxy-2,9,9-trimethyl-5-methylene-, (1aR,2R,4aS,7aS,9aR)-; Alliacolide II |
| IUPAC Name | (1S,5S,8R,9R,11R)-5-hydroxy-8,12,12-trimethyl-4-methylidene-2,10-dioxatetracyclo[7.4.0.01,5.09,11]tridecan-3-one |
| Canonical SMILES | CC1CCC2(C(=C)C(=O)OC23C14C(O4)C(C3)(C)C)O |
| InChI | InChI=1S/C15H20O4/c1-8-5-6-13(17)9(2)10(16)18-14(13)7-12(3,4)11-15(8,14)19-11/h8,11,17H,2,5-7H2,1,3-4H3/t8-,11-,13+,14+,15-/m1/s1 |
| InChI Key | VLJBPLOIFLPLAP-AUCBNHOYSA-N |
Properties
| Antibiotic Activity Spectrum | fungi; neoplastics (Tumor) |
| Boiling Point | 451.9 °C at 760 mmHg |
| Melting Point | 155.5-156 °C |
| Density | 1.280 g/cm3 |
| Solubility | Soluble in Chloroform, Methanol |
Reference Reading
1. Anodic cyclization reactions: the total synthesis of alliacol a
John Mihelcic, Kevin D Moeller J Am Chem Soc. 2003 Jan 8;125(1):36-7. doi: 10.1021/ja029064v.
An anodic cyclization-Friedel Crafts alkylation strategy has been used to rapidly assemble the core ring system of alliacol A and to complete a formal total synthesis of the natural product. The anodic cyclization reaction was used to effect the coupling of a nucleophilic furan ring to the normally nucleophilic carbon of a silyl enol ether. The substrate for this initial cyclization reaction contained all of the carbons needed for completing the total synthesis. The electrolysis proceeded in high yield and could be accomplished with the use of a 6 V lantern battery.
2. Antibiotics from basidiomycetes. XIII. The alliacols A and B from Marasmius alliaceus (Jacq. ex Fr.) Fr
T Anke, W H Watson, B M Giannetti, W Steglich J Antibiot (Tokyo). 1981 Oct;34(10):1271-7. doi: 10.7164/antibiotics.34.1271.
Two antimicrobial and cytotoxic metabolites were isolated from fermentation broth of Marasmius alliaceus. The structures of the two crystalline antibiotics, alliacols A (6) and B (1) were elucidated by spectroscopic methods and chemical correlation with alliacolide (3). The alliacols show weak antibacterial and antifungal activity. Both antibiotics strongly inhibit DNA synthesis in cells of the ascitic form of Ehrlich carcinoma at concentrations of 2 approximately 5 microgram/ml. Both alliacols A and B react with cysteine to form adducts with strongly reduced biological activities.
3. Oxidative cyclizations: the asymmetric synthesis of (-)-alliacol A
John Mihelcic, Kevin D Moeller J Am Chem Soc. 2004 Jul 28;126(29):9106-11. doi: 10.1021/ja048085h.
A tandem anodic coupling-Friedel-Crafts alkylation strategy has been used to rapidly complete the asymmetric synthesis of alliacol A. The anodic oxidation reaction allowed for the generation of a new bond between two nucleophiles. In the synthesis, the absolute stereochemistry of the final natural product is set relative to a methyl group that is incorporated early in the sequence using an asymmetric Michael 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 ╳
