Butalactin
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| Category | Antibiotics |
| Catalog number | BBF-00190 |
| CAS | 132605-69-7 |
| Molecular Weight | 242.22 |
| Molecular Formula | C11H14O6 |
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Description
Butalactin is a new butanolide antibiotic produced by Streptomyces sp. HIL Y-8636923. It has weak anti-Gram-positive and negative bacteria activity.
Specification
| IUPAC Name | (3R,4S)-3-hydroxy-4-(hydroxymethyl)-3-[(E)-3-(3-methyloxiran-2-yl)prop-2-enoyl]oxolan-2-one |
| Canonical SMILES | CC1C(O1)C=CC(=O)C2(C(COC2=O)CO)O |
| InChI | InChI=1S/C11H14O6/c1-6-8(17-6)2-3-9(13)11(15)7(4-12)5-16-10(11)14/h2-3,6-8,12,15H,4-5H2,1H3/b3-2+/t6?,7-,8?,11+/m0/s1 |
| InChI Key | NDWZCKPIOWDQOR-YIVRGOCWSA-N |
Properties
| Appearance | Oil |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 485°C at 760 mmHg |
| Density | 1.373 g/cm3 |
| Solubility | Soluble in Water, methanol, acetonitrile, chloroform |
Reference Reading
1. Butalactin, a new butanolide antibiotic. Taxonomy, fermentation, isolation and biological activity
C M Franco, U P Borde, E K Vijayakumar, S Chatterjee, J Blumbach, B N Ganguli J Antibiot (Tokyo). 1991 Feb;44(2):225-31. doi: 10.7164/antibiotics.44.225.
Butalactin, [2-(4',5'-epoxy-hex-2'(E)-en)oyl-2-hydroxy-3-hydroxymethyl-2, 3-(Z)-butanolide] is a new antibiotic produced by Streptomyces sp. HIL Y-86,36923. Taxonomically, the producing organism most closely resembles Streptomyces corchorusii. The strain also produces cineromycin B. Though butalactin is structurally related to 'signal molecules' such as A-factor, the anthracycline inducing factors and the virginiae butanolides, it does not show inducing activity for antibiotic production or aerial mycelium formation in the indicator strain. Butalactin possesses a weak antibiotic activity against Gram-positive and Gram-negative bacteria.
2. Stereoselective synthesis and structure of butalactin and lactone II isolated from Streptomyces species
Toshihiko Ueki, Takamasa Kinoshita Org Biomol Chem. 2004 Oct 7;2(19):2777-85. doi: 10.1039/B407820A. Epub 2004 Aug 23.
Butalactin (1a) and lactone II (2a) have been synthesized starting from (S)-malic acid and sorbic acid by a straightforward route. The absolute stereochemistry of 1a and 2a was unambiguously established by this synthesis.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
