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

Lasiocarpine is a hepatotoxic alkaloid found in Heliotropium lasiocarpum, which forms colorless leaflets from petroleum ether and has a specific rotation of [α]20D 4° (EtOH). It is readily soluble in benzene (C6H6) or ethanol (EtOH) but only slightly soluble in water (H2O). Its chemical structure is angelyllasiocarpylheliotridine, with both hydroxyls in heliotridine being esterified. Lasiocarpine is a colorless to beige crystalline solid.

Uses

Lasiocarpine is a hepatotoxic and carcinogenic food contaminant. Due to its toxic properties, it is not used for any beneficial applications in industries. However, understanding its chemical properties and potential effects on health can help in developing methods to detect and mitigate its presence in food products, ensuring safety and quality control.

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