lasiocarpine
lasiocarpine Basic information
- Product Name:
- lasiocarpine
- Synonyms:
-
- lasiocarpine
- 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)]-
- (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-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
- Aids002693
- Aids-002693
- Nsc30625
- Lasiocarpin
- CAS:
- 303-34-4
- MF:
- C21H33NO7
- MW:
- 411.49
- Mol File:
- 303-34-4.mol
lasiocarpine Chemical Properties
- 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)
- Water Solubility
- 6.754g/L(temperature not stated)
- Stability:
- Stable, but is readily hydrolyzed in basic solution and readily oxidized by oxidizing agents. Reacts slowly with atmospheric oxygen.
- LogP
- 1.280
- IARC
- 2B (Vol. 10, Sup 7) 1987
- EPA Substance Registry System
- Lasiocarpine (303-34-4)
Safety Information
- RIDADR
- 1544
- HazardClass
- 6.1(b)
- PackingGroup
- III
- Hazardous Substances Data
- 303-34-4(Hazardous Substances Data)
lasiocarpine Usage And Synthesis
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
Chemical Properties
colourless to beige crystalline solid
Uses
Lasiocarpine is a hepatotoxic and carcinogenic food contaminant.
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.
References
Men'shikov., Ber., 65,974 (1932)
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lasiocarpine(303-34-4)Related Product Information
- VERATRIDINE
- Xanthiazone
- menisdaurin
- daurisoline
- L-Hyoscyamine
- Daurinoline
- VERATRINE
- 2-[2-(Methylamino)benzoyl]-3,4-dihydro-β-carboline-1(2H)-one
- Xanthiside
- veratramine
- lasiocarpine
- ALLYL 2-ETHYLBUTYRATE
- ETHOXYPYRROLIDINE(S-3-)
- symphytine
- HELIOTRIDINE
- (S)-3-METHOXYPYRROLIDINE
- 2,3,5,7A-TETRAHYDRO-1H-PYRROLIZINE