303-34-4

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 NO: 303-34-4
• Molecular Formula: C21H33NO7
• Molecular Weight: 411.492
• Mol File: 303-34-4.mol
• Article Data: 0

Chemical Properties

• Melting Point: 96.5-97.0℃
• Boiling Point: 531.2°C (rough estimate)
• Flash Point: 268.1°C
• Appearance: colourless to beige crystalline solid
• Density: 1.21±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0mmHg at 25°C
• 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 oxy
• CAS DataBase Reference: lasiocarpine(CAS DataBase Reference)
• NIST Chemistry Reference: lasiocarpine(303-34-4)
• EPA Substance Registry System: lasiocarpine(303-34-4)

Safety Data

• RIDADR: 1544
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 303-34-4(Hazardous Substances Data)

Usage

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)

InChI:InChI=1/C21H33NO7/c1-7-13(2)18(23)29-16-9-11-22-10-8-15(17(16)22)12-28-19(24)21(26,14(3)27-6)20(4,5)25/h7-8,14,16-17,25-26H,9-12H2,1-6H3/b13-7-/t14-,16-,17+,21?/m0/s1