Alliacolide
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| Category | Antibiotics |
| Catalog number | BBF-03734 |
| CAS | 66389-08-0 |
| Molecular Weight | 266.33 |
| Molecular Formula | C15H22O4 |
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Description
It is produced by the strain of Marasmius alliaceus (Basidiomycetes). It inhibits the activity of Ehrlician ascites cancer cells.
Specification
| Synonyms | Alliacolide-1; 8H-Oxireno[1,4-b]furan-6(2H)-one, hexahydro-4a-hydroxy-2,5,9,9-tetramethyl-, [2R-(1aR*,2alpha,4abeta,5alpha,7aS*,9aalpha)]-; (1aR,2R,4aS,5S,7aS,9aR)-4a-hydroxy-2,5,9,9-tetramethylhexahydro-8H-oxireno[2',3':1,7a]indeno[3a,4-b]furan-6(2H)-one |
| IUPAC Name | (1S,4S,5S,8R,9R,11R)-5-hydroxy-4,8,12,12-tetramethyl-2,10-dioxatetracyclo[7.4.0.01,5.09,11]tridecan-3-one |
| Canonical SMILES | CC1CCC2(C(C(=O)OC23C14C(O4)C(C3)(C)C)C)O |
| InChI | InChI=1S/C15H22O4/c1-8-5-6-13(17)9(2)10(16)18-14(13)7-12(3,4)11-15(8,14)19-11/h8-9,11,17H,5-7H2,1-4H3/t8-,9-,11-,13+,14+,15-/m1/s1 |
| InChI Key | LLRILYDNXOIONB-PMKYJIPRSA-N |
Properties
| Appearance | White Crystal |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 434.1°C at 760 mmHg |
| Melting Point | 192-194°C |
| Density | 1.26 g/cm3 |
| Solubility | Soluble in Chloroform |
Reference Reading
1. 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.
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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 ╳
