Retrorsine N-oxide – CAS 15503-86-3

Abstract

Retrorsine N-oxide (CAS 15503-86-3) is the oxidized form of a pyrrolizidine alkaloid (PA) isolated from the Senecio genus. Retrorsine N-oxide can be present in honey made from the nectar of the plant and has become a compound of interest for monitoring Pyrrolizidine alkaloid (PA) content in honey and related products.

PAs are secondary metabolites in plants; about half of these alkaloids exhibit toxicity and carcinogenicity. Pyrrolizidine alkaloids poison grazing animals and domestic livestock through contaminated plants or feed. These alkaloids then poison humans through contaminated food (e.g., grains, honey, and milk), herbal medicine, and supplements. The plant is also toxic to livestock, and considered and undesirable wildflower.

Find the entire collection of pyrrolizidine alkaloids here.

Compound Details

CAS

15503-86-3

Molecular Weight

367.4

Chemical Formula

C18H25NO7

IUPAC

(1R,4Z,6R,7S,14S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

Synonyms

Retrorsine oxide
Retrorsine N-oxide

SMILES

CC=C1CC(C(C(=O)OCC2=CC[N+]3(C2C(CC3)OC1=O)[O-])(CO)O)C

Purity

95%+

Storage Temperature

Below -18 degrees C

Storage Conditions

Dry, freezer

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Products are sold as laboratory reference materials, to be used for diagnostic and in vivo testing. The samples are not certified for veterinary or human use. 

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Product information is from published literature. Due to the nature of scientific experimentation, results or specific product application may vary (e.g., selectivity, detector response). If you have questions about the product, its application, and associated analytics, please contact our technical support team.

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