Brefeldin C
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| Category | Antibiotics |
| Catalog number | BBF-00587 |
| CAS | 73899-78-2 |
| Molecular Weight | 264.36 |
| Molecular Formula | C16H24O3 |
| Purity | 95% |
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Description
Brefeldin is an antibiotic produced by Penicillum brefeldianum S-464, Pen. cyaneum S-ll, Pen. decumbens, Pen. simplicissimum S-545, etc.
Specification
| Synonyms | (1S,2Z,7S,10Z,12R,13R)-12-hydroxy-7-methyl-8-oxabicyclo[11.3.0]hexadeca-2,10-dien-9-one; 4H-Cyclopent(f)oxacyclotridecin-4-one, 1,6,7,8,9,11a,12,13,14,14a-decahydro-1-hydroxy-6-methyl-, (1R-(1R*,2E,6S*,10E,11aS*,14aR*))- |
| IUPAC Name | (1R,2R,3Z,7S,11Z,13S)-2-hydroxy-7-methyl-6-oxabicyclo[11.3.0]hexadeca-3,11-dien-5-one |
| Canonical SMILES | CC1CCCC=CC2CCCC2C(C=CC(=O)O1)O |
| InChI | InChI=1S/C16H24O3/c1-12-6-3-2-4-7-13-8-5-9-14(13)15(17)10-11-16(18)19-12/h4,7,10-15,17H,2-3,5-6,8-9H2,1H3/b7-4-,11-10-/t12-,13+,14+,15+/m0/s1 |
| InChI Key | DDFOHHVPBOQQDW-QHGHZAPRSA-N |
Properties
| Boiling Point | 445.4ºC at 760 mmHg |
| Melting Point | 163-166°C |
| Density | 1.032g/cm3 |
Reference Reading
1.Macrolide biosynthesis: stereochemistry of the hydroxylation of brefeldin C.
Gonzalez de la Parra M1, Hutchinson CR. J Antibiot (Tokyo). 1987 Aug;40(8):1170-4.
Brefeldin C (2) is the penultimate intermediate in the biosynthetic pathway to brefeldin A (1). Using stereospecifically 2H-labeled forms of 2, the hydroxylation of 2 to 1 is shown to involve stereospecific removal of the 7 pro-S hydrogen from 2.
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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 ╳
