| Identification | Back Directory | [Name]
lasiocarpine | [CAS]
303-34-4 | [Synonyms]
Nsc30625
Aids002693
Aids-002693
Lasiocarpin
lasiocarpine
2-Methyl-2-butenoic acid 7-[[2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy]methyl]-2,3,5,7A-tetrahydro-1H-pyrrolizin-1-yl ester
(Z)-2-Methyl-2-butenoic acid (1S)-7-[[[(2R)-2,3-dihydroxy-2-[(S)-1-methoxyethyl]-3-methylbutanoyl]oxy]methyl]-2,3,5,7aβ-tetrahydro-1H-pyrrolizin-1-yl ester
2-Butenoic acid, 2-methyl-, 7[[(2,3-dihydroxy-2-(1-methoxyethyl)-3-methyl-1-oxobutoxy] methyl]-2,3,5,7a-tetrahydro-1H-prrolizin-1-yl ester, [1S-[1alpha(Z), 7(2S*, 3R*), 7aalpha)]- | [Molecular Formula]
C21H33NO7 | [MDL Number]
MFCD31631257 | [MOL File]
303-34-4.mol | [Molecular Weight]
411.492 |
| Chemical Properties | Back Directory | [Appearance]
colourless to beige crystalline solid | [Melting point ]
96.5-97.0℃ | [alpha ]
D -4° (10% alc) | [Boiling point ]
531.2°C (rough estimate) | [density ]
1.21±0.1 g/cm3 (20 ºC 760 Torr) | [refractive index ]
1.5614 (estimate) | [pka]
11.99±0.29(Predicted) | [Stability:]
Stable, but is readily hydrolyzed in basic solution and readily oxidized by oxidizing agents. Reacts slowly with atmospheric oxygen. | [Water Solubility ]
6.754g/L(temperature not stated) | [LogP]
1.280 | [IARC]
2B (Vol. 10, Sup 7) 1987 | [EPA Substance Registry System]
Lasiocarpine (303-34-4) |
| Hazard Information | Back Directory | [Chemical Properties]
colourless to beige crystalline solid | [General Description]
Colorless plates or beige crystalline solid. | [Air & Water Reactions]
Decomposes slowly on standing in air at room temperature. Insoluble in water. | [Reactivity Profile]
lasiocarpine is readily hydrolyzed by alkali. Reacts readily with oxidizing agents. Reacts slowly with atmospheric oxygen . | [Health Hazard]
ACUTE/CHRONIC HAZARDS: When heated to decomposition lasiocarpine emits toxic fumes of nitrogen oxides. | [Fire Hazard]
Flash point data for lasiocarpine are not available; however, lasiocarpine is probably combustible. | [Description]
A hepatotoxic alkaloid found in Heliotropiurn lasiocarpurn, the base forms
colourless leaflets from petroleum ether and has [α]20D - 4° (EtOH). It is readily
soluble in C6H6 or EtOH but only slightly so in H20. On alkaline hydrolysis it
furnishes angelic acid and heliotridine, C8H1302N, m.p. 116.5-118°C, forming
a hydrochloride, m.p. 122-4°C and the benzoyl derivative hydrochloride, m.p.
180°C. On catalytic hydrogenation it yields a base, C13H230 2N, b.p. 123-5°Cj
8 mm; [α]D + 3.8° (EtOH), yielding a crystalline picrate, m.p. 157 _9°C, and
lasiocarpic acid, C8H160 S, m.p. 95-7°C; [α]D + 10.6° (EtOH). The structure is
therefore angelyllasiocarpylheliotridine, both hydroxyls in heliotridine being
es terifie d | [Uses]
Lasiocarpine is a hepatotoxic and carcinogenic food contaminant. | [References]
Men'shikov., Ber., 65,974 (1932) |
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