6209-65-0

Basic information

• Product Name: Heliotrine, 4-oxide
• Synonyms: Heliotrine, 4-oxide;heliotrine N-oxide;Heliotrin-N-oxid
• CAS NO: 6209-65-0
• Molecular Formula: C16H27NO6
• Molecular Weight: 329.39
• Mol File: 6209-65-0.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• PKA: 12.08±0.29(Predicted)
• CAS DataBase Reference: Heliotrine, 4-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Heliotrine, 4-oxide(6209-65-0)
• EPA Substance Registry System: Heliotrine, 4-oxide(6209-65-0)

Safety Data

• Hazardous Substances Data: 6209-65-0(Hazardous Substances Data)

Usage

Description

Heliotrine, 4-oxide is a derivative of Heliotrine (H235110), a monoester pyrrolizidine alkaloid that can be found in the seeds of Heliotropium indicum, one of the most widely used herbs in India. It is known for its mutagenic activity and ganglion blocking activity.

Uses

Used in Pharmaceutical Industry:
Heliotrine, 4-oxide is used as a pharmaceutical compound for its mutagenic and ganglion blocking properties. These characteristics make it a potential candidate for the development of new drugs targeting specific biological pathways.
Used in Research Applications:
Heliotrine, 4-oxide is used as a research tool for studying the effects of mutagenic and ganglion blocking activities on various biological systems. This can contribute to the understanding of certain diseases and the development of targeted therapies.
Used in Traditional Medicine:
Heliotrine, 4-oxide is used in traditional medicine, particularly in India, where the herb Heliotropium indicum has been widely utilized. Its presence in the seeds of the plant may contribute to the herb's overall therapeutic effects.

InChI:InChI=1/C16H27NO6/c1-10(2)16(20,11(3)22-4)15(19)23-9-12-5-7-17(21)8-6-13(18)14(12)17/h5,10-11,13-14,18,20H,6-9H2,1-4H3/t11?,13-,14-,16?,17?/m0/s1

Upstream product

• 303-33-3 Heliotrine 

Relevant articles and documents

Characteristic ion clusters as determinants for the identification of pyrrolizidine alkaloid N-oxides in pyrrolizidine alkaloid-containing natural products using HPLC-MS analysis

Pyrrolizidine alkaloid (PA)-containing plants are widely distributed in the world. PAs are hepatotoxic, affecting livestock and humans. PA N-oxides are often present together with PAs in plants and also exhibit hepatotoxicity but with less potency. HPLC-MS is generally used to analyze PA-containing herbs, although PA references are unavailable in most cases. However, to date, without reference standards, HPLC-MS methodology cannot distinguish PA N-oxides from PAs because they both produce the same characteristic ions in mass spectra. In the present study, the mass spectra of 10 PA N-oxides and the corresponding PAs were systemically investigated using HPLC-MS to define the characteristic mass fragment ions specific to PAs and PA N-oxides. Mass spectra of toxic retronecine-type PA N-oxides exhibited two characteristic ion clusters at m/z 118-120 and 136-138. These ion clusters were produced by three unique fragmentation pathways of PA N-oxides and were not found in their corresponding PAs. Similarly, the nontoxic platynecine-type PA N-oxides also fragmented via three similar pathways to form two characteristic ion clusters at m/z 120-122 and 138-140. Further application of using these characteristic ion clusters allowed successful and rapid identification of PAs and PA N-oxides in two PA-containing herbal plants. Our results demonstrated, for the first time, that these characteristic ion clusters are unique determinants to discriminate PA N-oxides from PAs even without the availability of reference samples. Our findings provide a novel and specific method to differentiate PA N-oxides from PAs in PA-containing natural products, which is crucial for the assessment of their intoxication.