Lasiocarpine N-oxide

Catalog Number	ACM127300
CAS Number	127-30-0
Synonyms	(1S)-1β-[(Z)-2-Methyl-2-butenoyloxy]-2,3,5,7aβ-tetrahydro-7-[[[(2R)-2,3-dihydroxy-2-[(S)-1-methoxyethyl]-3-methylbutanoyl]oxy]methyl]-1H-pyrrolizine 4-oxide
Molecular Weight	427.5
InChI	InChI=1S/C21H33NO8/c1-7-13(2)18(23)30-16-9-11-22(27)10-8-15(17(16)22)12-29-19(24)21(26,14(3)28-6)20(4,5)25/h7-8,14,16-17,25-26H,9-12H2,1-6H3/b13-7-/t14-,16-,17+,21-,22/m0/s1
InChI Key	AABILZKQMVKFHP-LRBDFNDQSA-N
Melting Point	134-135 °C
Purity	95%+
Complexity	745
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	4
Exact Mass	427.22061701
Heavy Atom Count	30
Hydrogen Bond Acceptor Count	8
Hydrogen Bond Donor Count	2
Isomeric SMILES	C/C=C(/C)\C(=O)O[C@H]1CC[N+]2([C@@H]1C(=CC2)COC(=O)[C@@]([C@H](C)OC)(C(C)(C)O)O)[O-]
Monoisotopic Mass	427.22061701
PhysicalState	Powder
Rotatable Bond Count	10
Topological Polar Surface Area	120 Ų

Case Study

Application of Lasiocarpine N-oxide in the Determination of N-Oxides of Pyrrolizidine Alkaloids

Cao, Yu, et al. Phytochemical analysis, 2008, 19(6), 526-533.

This work highlights the analytical importance of N-oxides in the safety assessment of pyrrolizidine alkaloid-containing herbs. Model pyrrolizidine alkaloids involved include senecionine and lasiocarpine and their N-oxides.
Quantitative method with lasiocarpine and lasiocarpine-N-oxide
· Due to the unavailability of authentic standards for the alkaloids detected, this study quantifies the results in terms of "equivalents of lasiocarpine (3)" for the pyrrolizidine alkaloids, and "equivalents of lasiocarpine-N-oxide (3-NO)" for the N-oxides.
· Calibration curves were created for lasiocarpine (y = 1.1x2 + 8.1x, r2 = 0.9999) and lasiocarpine-N-oxide (y = 0.4x2 + 4.7x, R2 = 1) using six data points ranging from 0.5 to 25 μg/mL.
· Initially, the pyrrolizidine alkaloids or their N-oxides were analyzed in reconstructed ion chromatograms to identify their specific molecular ion adduct (MH+). The obtained peak area was normalized by dividing it by the area of the internal standard, heliotrine (2), in the sample.
· The alkaloid levels were then determined from the calibration curves. While an extensive optimization and validation were not performed due to the study's scope, the HPLC-ESI ion trap MS method's limit of detection and limit of quantitation were estimated by analyzing dilutions (1, 0.5, 0.25, 0.1, 0.05, and 0.0125 μg/mL) of senecionine, lasiocarpine, and lasiocarpine-N-oxide in methanol.

Custom Q&A

What is the chemical formula of lasiocarpine N-oxide?

The chemical formula of lasiocarpine N-oxide is C21H33NO8.

What is the molecular weight of lasiocarpine N-oxide?

The molecular weight of lasiocarpine N-oxide is 427.48862.

At what temperature does lasiocarpine N-oxide melt?

Lasiocarpine N-oxide melts at 134-5°C.

What is the hazardous classification of lasiocarpine N-oxide?

Lasiocarpine N-oxide is classified as HazardClass 6.1(b).

What is the toxicity level of lasiocarpine N-oxide in rats?

The LD50 (lethal dose 50%) value for lasiocarpine N-oxide in rats, intraperitoneal route, is 181mg/kg.

What natural source contains lasiocarpine N-oxide?

The seeds of Heliotropium europaeum have been shown to contain lasiocarpine N-oxide.

What can lasiocarpine N-oxide be reduced to?

Lasiocarpine N-oxide can be reduced to Lasiocarpine.

How has mass spectrometry been used to detect lasiocarpine N-oxide?

Lasiocarpine N-oxide has been found to be higher in varied tea bags, herbal drugs, and honey by mass spectrometry.

What is one of the references for information on lasiocarpine N-oxide?

One of the references for information on lasiocarpine N-oxide is a publication by Culvenor, Drummond, and Price in the Austral. J. Chem in 1954.

What are some of the reported uses of lasiocarpine N-oxide?

Lasiocarpine N-oxide is a natural compound found in varied tea bags, herbal drugs, and honey, as reported by mass spectrometry.

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