CAS 303-33-3
:(+)-Heliotrine
Description:
(+)-Heliotrine, with the CAS number 303-33-3, is a naturally occurring alkaloid primarily derived from plants in the Heliotropium genus. This compound is characterized by its bicyclic structure, which includes a pyrrolidine ring fused to a cyclopentane ring. It exhibits a chiral center, resulting in its designation as the (+) enantiomer, which is known for its specific optical activity. (+)-Heliotrine is recognized for its potential biological activities, including antimicrobial and cytotoxic properties, making it of interest in pharmacological research. The compound is typically found in trace amounts in various plant species and can be extracted through methods such as steam distillation or solvent extraction. Its solubility is generally higher in organic solvents than in water, which is common for many alkaloids. Due to its structural features, (+)-Heliotrine may also participate in various chemical reactions, contributing to its utility in synthetic organic chemistry. However, it is important to handle this compound with care, as some alkaloids can exhibit toxic effects at certain concentrations.
Formula:C16H27NO5
InChI:InChI=1S/C16H27NO5/c1-10(2)16(20,11(3)21-4)15(19)22-9-12-5-7-17-8-6-13(18)14(12)17/h5,10-11,13-14,18,20H,6-9H2,1-4H3/t11-,13+,14-,16+/m1/s1
InChI key:InChIKey=LMFKRLGHEKVMNT-UJDVCPFMSA-N
SMILES:C(OC([C@@]([C@H](OC)C)([C@@H](C)C)O)=O)C=1[C@]2(N(CC1)CC[C@@H]2O)[H]
Synonyms:- (+)-Heliotrine
- (1-Hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl 2-hydroxy-2-isopropyl-3-methoxybutanoate
- (1-Hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl-2-hydroxy-2-isopropyl-3-methoxybutanoat
- 2-Hydroxy-2-isopropyl-3-méthoxybutanoate de (1-hydroxy-2,3,5,7a-tétrahydro-1H-pyrrolizin-7-yl)méthyle
- 7S-Heliotrine
- Butanoic acid, 2-hydroxy-2-(1-methoxyethyl)-3-methyl-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, [1S-[1α,7[R*(S*)],7aα]]-
- Butanoic acid, 2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methyl-, [(1S,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl ester, (2S)-
- butanoic acid, 2-hydroxy-3-methoxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester
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Found 10 products.
Butanoic acid, 2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methyl-, [(1S,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl ester, (2S)-
CAS:Formula:C16H27NO5Molecular weight:313.3893Heliotrine 100 µg/mL in Water
CAS:Controlled ProductFormula:C16H27NO5Color and Shape:Single SolutionMolecular weight:313.3893Heliotrine
CAS:Heliotrine leads to apoptosis of the human hepatoma cell line HepaRG.Formula:C16H27NO5Purity:98%Color and Shape:SolidMolecular weight:313.39Heliotrine
CAS:Natural alkaloidFormula:C16H27NO5Purity:≥ 85.0 % (HPLC)Color and Shape:PowderMolecular weight:313.4Heliotrine-D7 Hydrochloride Salt
CAS:Controlled ProductFormula:C16H20D7NO5·HClColor and Shape:NeatMolecular weight:316.4087S-Heliotrine
CAS:7S-Heliotrine is a naturally occurring pyrrolizidine alkaloid, which is derived predominantly from plants of the Boraginaceae family, such as Heliotropium species. This compound's mode of action involves bioactivation by cytochrome P450 enzymes to form highly reactive metabolites, which subsequently bind to cellular macromolecules, leading to cytotoxicity and potential genotoxicity. The primary impact of these reactive species is hepatotoxicity, as they can induce liver damage and veno-occlusive disease. As such, 7S-Heliotrine is often used as a model compound in research studies investigating mechanisms of alkaloid-induced liver injury, as well as contributing to broader studies on chemical carcinogenesis and genotoxic stress responses. Understanding its effects is critical in assessing the risks associated with dietary or medicinal exposure to pyrrolizidine alkaloid-containing plants.Formula:C16H27NO5Purity:Min. 95%Color and Shape:PowderMolecular weight:313.39 g/mol
![Butanoic acid, 2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methyl-, [(1S,7aR)-2,3,5,7a-tetrahydro-1-hydrox…](/_next/image/?url=https%3A%2Fstatic.cymitquimica.com%2Fproducts%2FIN%2Fthumb%2FDA002ZJX.jpg&w=3840&q=75)
