lasiocarpine

lasiocarpine Structure
CAS No.
303-34-4
Chemical Name:
lasiocarpine
Synonyms
Nsc30625;AI3-51770;Aids002693;Aids-002693;Lasiocarpin;lasiocarpine;(-)-Lasiocarpine;7-Angelyleuropine;Europine 7-angelate;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
CBNumber:
CB7875229
Molecular Formula:
C21H33NO7
Molecular Weight:
411.49
MOL File:
303-34-4.mol
MSDS File:
SDS
Modify Date:
2023/5/25 18:01:18

lasiocarpine 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

Risk and Safety Statements

Symbol(GHS) 
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P264-P270-P301+P310-P321-P330-P405-P501
RIDADR  1544
HazardClass  6.1(b)
PackingGroup  III

lasiocarpine Chemical Properties,Uses,Production

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)

lasiocarpine Preparation Products And Raw materials

Raw materials

Preparation Products

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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 2-Butenoic acid, 2-methyl-, (1S,7aR)-7-[[(2R)-2,3-dihydroxy-2-[(1R)-1-methoxyethyl]-3-methyl-1-oxobutoxy]methyl]-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester, (2Z)- (-)-Lasiocarpine 7-Angelyleuropine AI3-51770 Europine 7-angelate 2-Butenoic acid,2-methyl-,(1S,7aR)-7-[[(2R)-2,3-dihydroxy-2-[(1S)-1-methoxyethyl]-3-methyl-1-oxobutoxy]methyl]-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-ylester, (2Z)- 303-34-4 C21H33NO7