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邦克里克酸

CAS 11076-19-0C28H38O7MW 486.6

邦克里克酸(CAS 11076-19-0):分子式 C28H38O7、分子量 486.6。

产品概览

CAS号11076-19-0
分子式C28H38O7
分子量486.6
熔点50-60 °C
LogP5.7
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.

应用领域

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.。

技术档案

这个产品是什么

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)。

识别信息

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

常见问题

邦克里克酸 的 CAS 号是多少?

邦克里克酸 的 CAS 登记号为 11076-19-0。

邦克里克酸 的分子式与分子量是多少?

分子式 C28H38O7,分子量 486.6。

邦克里克酸 还有哪些别名?

别名/同义词:邦克里克酸、BONGKREKIC ACID。

邦克里克酸 的登记用途是什么?

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.。

PubChem 公开数据

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。

各数据库的登记标识

CAS Registry Number11076-19-0
PubChem CID6433556
Molecular formulaC28H38O7
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

计算分子描述符

Molecular Weight486.6
XLogP35.7
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count7
Rotatable Bond Count17
Exact Mass486.26175355
Monoisotopic Mass486.26175355
Topological Polar Surface Area121
Heavy Atom Count35

在册的理化数值

Melting Point50-60 °C

在册的记载用途

    Laboratory chemicals, synthesis of substances.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.

    同义词与商品名

    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,

    GHS 危害分类

    Reported hazard statementsH301 (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)

    公开数据库对它的描述

    BONGKREKIC ACID · CAS 11076-19-0 · C28H38O7. UNII L7V4I673D2. Melting Point: 50-60 °C.

    物理形态与操作说明

    数据来源:PubChem / Wikidata;与随货 COA 不一致时以 COA 为准。

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