邦克里克酸(CAS 11076-19-0):分子式 C28H38O7、分子量 486.6。
| CAS号 | 11076-19-0 |
|---|---|
| 分子式 | C28H38O7 |
| 分子量 | 486.6 |
| 熔点 | 50-60 °C |
| LogP | 5.7 |
| 应用领域 | Uses: Laboratory chemicals、synthesis of substances.、Methods of Manufacturing: Bongkrekic (or bongkrek) acid、produced in fermented coconut by a pathovar of the bacterium Burkholderia gladioli、is a more potent respiratory toxin than cyanide. Its first total synthesis was reported by E. J. Corey and A. Tramontano in 1984、and M. Shindo and co-workers described improved syntheses in 2004 and 2009. Most recently、S. V. Ley used three stereospecific palladium cross-coupling reactions to accomplish an even better synthesis.、General Manufacturing Information: An antibiotic produced by Pseudomonas cocovenenans. It is an inhibitor of mitochondrial ADP、ATP translocases. Specifically、it blocks adenine nucleotide efflux from mitochondria by enhancing membrane binding.、Natural product、Anti-Bacterial Agent、Anti-Infective Agent、Drug、Therapeutic Agent、Tempe bongkrek is an Indonesian food made by fermentation of coconut presscake or coconut milk residue Rhizopus oligosporus. Consumption of tempe bongkrek is associated with a food-borne human intoxication and significant numbers of deaths annually. The bacterium Burkholderia cocovenenans、which is the causative organism、produces two toxins、toxoflavin and bongkrekic acid (also commonly referred to as bongkrek acid). The reasons why these poisonings occur only in a very limited number of foods and only in isolated regions of the world are unclear. Our preliminary experiments in defined media and coconut investigated several compositional and environmental factors and suggested that lipid type and、or concentration were important. The effect of lipid concentration and fatty acid type on the production of bongkrekic acid by B. cocovenenans was examined by adding different amounts of coconut fat or individual free fatty acids to defatted and sterilized Rich Coconut Media (dRCM). The dRCM with added lipid was inoculated with B. cocovenenans、incubated at 30 degrees C for 5 days and the amount of bongkrekic acid formed quantified by HPLC. Coconut fat concentrations of 10% (dry basis) or less did not result in detectable amounts of bongkrekic acid even though the B. cocovenenans grew to high levels. Forty and 50% coconut fat resulted in as much as 1.4 mg、g bonkrekic acid (dry weight) at the same level of growth. Of eight saturated fatty acids tested、only lauric (12:0)、myristic (14:0)、and palmitic (16:0) acids stimulated the production of detectable amounts of toxin. When four 18-carbon free fatty acids with different degrees of saturation were compared、significant amounts of bongkrekic acid (2.62 mg、g dry weight) were produced only with oleic acid (18:1). These data indicate that the concentration and type of lipid in the substrate is critical for bongkrekic acid formation. This may explain why bongkrekic acid intoxication is limited to certain foods. Outbreaks associated with foods containing less than 20% fat may be a result of toxoflavin formation and not bongkrekic acid formation.、One of two toxic antibiotic principles produced by Pseudomonas cocovenenans on partially defatted coconut、the other being toxoflavin、q.v. Name derived from "bongkrek"、a molded coconut product from Indonesia which becomes highly poisonous when P. cocovenenans outgrows the mold. |
登记用途:Uses: Laboratory chemicals、synthesis of substances.、Methods of Manufacturing: Bongkrekic (or bongkrek) acid、produced in fermented coconut by a pathovar of the bacterium Burkholderia gladioli、is a more potent respiratory toxin than cyanide. Its first total synthesis was reported by E. J. Corey and A. Tramontano in 1984、and M. Shindo and co-workers described improved syntheses in 2004 and 2009. Most recently、S. V. Ley used three stereospecific palladium cross-coupling reactions to accomplish an even better synthesis.、General Manufacturing Information: An antibiotic produced by Pseudomonas cocovenenans. It is an inhibitor of mitochondrial ADP、ATP translocases. Specifically、it blocks adenine nucleotide efflux from mitochondria by enhancing membrane binding.、Natural product、Anti-Bacterial Agent、Anti-Infective Agent、Drug、Therapeutic Agent、Tempe bongkrek is an Indonesian food made by fermentation of coconut presscake or coconut milk residue Rhizopus oligosporus. Consumption of tempe bongkrek is associated with a food-borne human intoxication and significant numbers of deaths annually. The bacterium Burkholderia cocovenenans、which is the causative organism、produces two toxins、toxoflavin and bongkrekic acid (also commonly referred to as bongkrek acid). The reasons why these poisonings occur only in a very limited number of foods and only in isolated regions of the world are unclear. Our preliminary experiments in defined media and coconut investigated several compositional and environmental factors and suggested that lipid type and、or concentration were important. The effect of lipid concentration and fatty acid type on the production of bongkrekic acid by B. cocovenenans was examined by adding different amounts of coconut fat or individual free fatty acids to defatted and sterilized Rich Coconut Media (dRCM). The dRCM with added lipid was inoculated with B. cocovenenans、incubated at 30 degrees C for 5 days and the amount of bongkrekic acid formed quantified by HPLC. Coconut fat concentrations of 10% (dry basis) or less did not result in detectable amounts of bongkrekic acid even though the B. cocovenenans grew to high levels. Forty and 50% coconut fat resulted in as much as 1.4 mg、g bonkrekic acid (dry weight) at the same level of growth. Of eight saturated fatty acids tested、only lauric (12:0)、myristic (14:0)、and palmitic (16:0) acids stimulated the production of detectable amounts of toxin. When four 18-carbon free fatty acids with different degrees of saturation were compared、significant amounts of bongkrekic acid (2.62 mg、g dry weight) were produced only with oleic acid (18:1). These data indicate that the concentration and type of lipid in the substrate is critical for bongkrekic acid formation. This may explain why bongkrekic acid intoxication is limited to certain foods. Outbreaks associated with foods containing less than 20% fat may be a result of toxoflavin formation and not bongkrekic acid formation.、One of two toxic antibiotic principles produced by Pseudomonas cocovenenans on partially defatted coconut、the other being toxoflavin、q.v. Name derived from "bongkrek"、a molded coconut product from Indonesia which becomes highly poisonous when P. cocovenenans outgrows the mold.。
邦克里克酸 是一种化工化合物,登记 CAS 号为 11076-19-0,分子式 C28H38O7(分子量 486.6)。
登记 CAS 号:11076-19-0
其分子式 C28H38O7 由 28 个碳、38 个氢、7 个氧 组成。
别名/同义词:邦克里克酸 · BONGKREKIC ACID
邦克里克酸 的 CAS 登记号为 11076-19-0。
分子式 C28H38O7,分子量 486.6。
别名/同义词:邦克里克酸、BONGKREKIC ACID。
登记用途:Uses: Laboratory chemicals、synthesis of substances.、Methods of Manufacturing: Bongkrekic (or bongkrek) acid、produced in fermented coconut by a pathovar of the bacterium Burkholderia gladioli、is a more potent respiratory toxin than cyanide. Its first total synthesis was reported by E. J. Corey and A. Tramontano in 1984、and M. Shindo and co-workers described improved syntheses in 2004 and 2009. Most recently、S. V. Ley used three stereospecific palladium cross-coupling reactions to accomplish an even better synthesis.、General Manufacturing Information: An antibiotic produced by Pseudomonas cocovenenans. It is an inhibitor of mitochondrial ADP、ATP translocases. Specifically、it blocks adenine nucleotide efflux from mitochondria by enhancing membrane binding.、Natural product、Anti-Bacterial Agent、Anti-Infective Agent、Drug、Therapeutic Agent、Tempe bongkrek is an Indonesian food made by fermentation of coconut presscake or coconut milk residue Rhizopus oligosporus. Consumption of tempe bongkrek is associated with a food-borne human intoxication and significant numbers of deaths annually. The bacterium Burkholderia cocovenenans、which is the causative organism、produces two toxins、toxoflavin and bongkrekic acid (also commonly referred to as bongkrek acid). The reasons why these poisonings occur only in a very limited number of foods and only in isolated regions of the world are unclear. Our preliminary experiments in defined media and coconut investigated several compositional and environmental factors and suggested that lipid type and、or concentration were important. The effect of lipid concentration and fatty acid type on the production of bongkrekic acid by B. cocovenenans was examined by adding different amounts of coconut fat or individual free fatty acids to defatted and sterilized Rich Coconut Media (dRCM). The dRCM with added lipid was inoculated with B. cocovenenans、incubated at 30 degrees C for 5 days and the amount of bongkrekic acid formed quantified by HPLC. Coconut fat concentrations of 10% (dry basis) or less did not result in detectable amounts of bongkrekic acid even though the B. cocovenenans grew to high levels. Forty and 50% coconut fat resulted in as much as 1.4 mg、g bonkrekic acid (dry weight) at the same level of growth. Of eight saturated fatty acids tested、only lauric (12:0)、myristic (14:0)、and palmitic (16:0) acids stimulated the production of detectable amounts of toxin. When four 18-carbon free fatty acids with different degrees of saturation were compared、significant amounts of bongkrekic acid (2.62 mg、g dry weight) were produced only with oleic acid (18:1). These data indicate that the concentration and type of lipid in the substrate is critical for bongkrekic acid formation. This may explain why bongkrekic acid intoxication is limited to certain foods. Outbreaks associated with foods containing less than 20% fat may be a result of toxoflavin formation and not bongkrekic acid formation.、One of two toxic antibiotic principles produced by Pseudomonas cocovenenans on partially defatted coconut、the other being toxoflavin、q.v. Name derived from "bongkrek"、a molded coconut product from Indonesia which becomes highly poisonous when P. cocovenenans outgrows the mold.。
邦克里克酸(CAS 11076-19-0)的独立参考数据,整理自公开化学数据库。
| CAS Registry Number | 11076-19-0 |
|---|---|
| PubChem CID | 6433556 |
| Molecular formula | C28H38O7 |
| IUPAC name | (2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)-20-(carboxymethyl)-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid |
| UNII (FDA) | L7V4I673D2 |
| Molecular Weight | 486.6 |
|---|---|
| XLogP3 | 5.7 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 17 |
| Exact Mass | 486.26175355 |
| Monoisotopic Mass | 486.26175355 |
| Topological Polar Surface Area | 121 |
| Heavy Atom Count | 35 |
| Melting Point | 50-60 °C |
|---|
BONGKREKIC ACID; 11076-19-0; Bongkrek acid; L7V4I673D2; (-)-BONGKREKIC ACID; CHEBI:77742; DTXSID00894840; 3-Carboxymethyl-17-methoxy-6,18,21-trimethyldocosa-2,4,8,12,14,18,20-heptaenedioic acid; RefChem:569813; DTXCID301324402; 998-673-7; Flavotoxin A; Bongkrekate; Bongkreksaure; UNII-L7V4I673D2; Isobongkrekic acid,
| Reported hazard statements | H301 (100%) |
|---|
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
BONGKREKIC ACID · CAS 11076-19-0 · C28H38O7. UNII L7V4I673D2. Melting Point: 50-60 °C.
数据来源:PubChem / Wikidata;与随货 COA 不一致时以 COA 为准。
English page: BONGKREKIC ACID