cas 315-22-0, MONOCROTALINE | Articles data

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315-22-0

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Human intestinal bacteria mediate reduction of the N-oxides of isoline and monocrotaline to the corresponding parent alkaloids
The role of human intestinal bacteria in the biotransformation of pyrrolizidine alkaloid N-oxides was investigated. Two naturally-occurring hepatotoxic pyrrolizidine alkaloids, isoline and monocrotaline and their N-oxides were incubated with a human fecal suspension in an in vitro model, respectively. The metabolites were isolated and purified by chromatographic techniques and identified by the spectral analyses and the metabolic profiles were further analyzed by a specific TLC method. Human intestinal bacteria showed high reduction effects on the pyrrolizidine alkaloid N-oxides but not on the resultant tertiary alkaloids, suggesting that IB may play a partial role in the cyclic conversion between each pyrrolizidine alkaloid and its N-oxide in vivo. This evidence implied the potential risk of the pyrrolizidine alkaloid-containing Chinese medicinal herbs to human health when used in decoctions.
Tang, Jun,Wang, Zhengtao,Akao, Teruaki,Hattori, Masao
p. 2027 - 2030
(2013)
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Total synthesis of optically active monocrotaline, a carcinogenic pyrrolizidine alkaloid possessing an eleven-membered retronecine dilactone
A total synthesis of the natural enantiomer of monocrotaline (1), a representative of carcinogenic pyrrolizidine alkaloids having an 11-membered retronecine dilactone was achieved through regioselective coupling of (+)-retronecine (3) and the optically active protected necic acid 8, the latter being prepared enantioselectively from the meso-diester 11.
Niwa, Haruki,Ogawa, Takeshi,Okamoto, Osamu,Yamada, Kiyoyuki
p. 10531 - 10548
(2007/10/02)

TOTAL SYNTHESIS OF OPTICALLY ACTIVE MONOCROTALINE, A CARCINOGENIC PYRROLIZIDINE ALKALOID HAVING AN 11-MEMBERED DILACTONE
Monocrotaline (1), a representative of carcinogenic pyrrolizidine alkaloids with an 11-membered dilactone has been synthesized in optically active form by virtue of regioselective coupling of (+)-retronecine (2) and the protected necic acid 3, the latter being synthesized enantioselectively from the meso-diester 4.
Niwa, Haruki,Okamoto, Osamu,Yamada, Kiyoyuki
p. 5139 - 5142
(2007/10/02)

Synthesis of monocrotaline by nucleophilic macrolactonization
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Vedejs,Ahmad,Larsen,Westwood
p. 3937 - 3938
(2007/10/02)

Chemical Properties

Appearance/Colour :white to light tan powder
Melting Point: 204 °C
Boiling Point: 537.3 °C at 760 mmHg
Flash Point:278.7 °C
Density: 1.35 g/cm³
Solubility:Soluble in DMSO (up to 50 mg/ml with warming), in Ethanol (up to 10 mg/ml with warming) or in organic solvents such as Chloroform (up to 50 mg/ml)
Storage Temp.:2-8°C
Vapor Pressure: 8.74E-14mmHg at 25°C
Refractive Index: 1.5500 (estimate)
PKA: 12.21±0.60(Predicted)
Merck: 13,6274
BRN: 48732
PSA: 96.30000
LogP: -0.45470

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Chemical Properties

Appearance/Colour :white to light tan powder

Melting Point: 204 °C

Boiling Point: 537.3 °C at 760 mmHg

Flash Point:278.7 °C

Density: 1.35 g/cm³

Solubility:Soluble in DMSO (up to 50 mg/ml with warming), in Ethanol (up to 10 mg/ml with warming) or in organic solvents such as Chloroform (up to 50 mg/ml)

Storage Temp.:2-8°C

Vapor Pressure: 8.74E-14mmHg at 25°C

Refractive Index: 1.5500 (estimate)

PKA: 12.21±0.60(Predicted)

Merck: 13,6274

BRN: 48732

PSA: 96.30000

LogP: -0.45470

Global suppliers and manufacturers of 315-22-0total 105 suppliers on LookChem

Article Database

315-22-0

Articles about 315-22-0Total 4 be found

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Chemical Properties

Appearance/Colour :white to light tan powder

Melting Point: 204 °C

Boiling Point: 537.3 °C at 760 mmHg

Flash Point:278.7 °C

Density: 1.35 g/cm3

Solubility:Soluble in DMSO (up to 50 mg/ml with warming), in Ethanol (up to 10 mg/ml with warming) or in organic solvents such as Chloroform (up to 50 mg/ml)

Storage Temp.:2-8°C

Vapor Pressure: 8.74E-14mmHg at 25°C

Refractive Index: 1.5500 (estimate)

PKA: 12.21±0.60(Predicted)

Merck: 13,6274

BRN: 48732

PSA: 96.30000

LogP: -0.45470

Global suppliers and manufacturers of 315-22-0total 105 suppliers on LookChem

Density: 1.35 g/cm³