Piperlongumine

• CAS: 20069-09-4
• Catalog Number: ACM20069094
• Category: Inhibitors
• Molecular Weight: 317.34
• Molecular Formula: C17H19NO5
• Description: Piperlongumine is a alkaloid, possesses ant-inflammatory, antibacterial, antiangiogenic, antioxidant, antitumor, and antidiabetic activities. Piperlongumine induces ROS, and induces apoptosis in cancer cell lines. Piperlongumine shows anti-cardiac fibrosis activity, suppresses myofibroblast transformation via suppression of the ERK1/2 signaling pathway. Piperlongumin could be used in the study of migrasome.
• Synonyms: 1-[(E)-3-(3,4,5-Trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
• InChI: InChI=1S/C17H19NO5/c1-21-13-10-12(11-14(22-2)17(13)23-3)7-8-16(20)18-9-5-4-6-15(18)19/h4,6-8,10-11H,5,9H2,1-3H3/b8-7+
• InChI Key: VABYUUZNAVQNPG-BQYQJAHWSA-N
• Melting Point: 124 °C
• Flash Point: 241.4°C
• Density: 1.223 g/cm³
• Solubility: water, 1030 mg/L @ 25 °C (est)
• Assay: 0.999
• Complexity: 473
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 0
• Exact Mass: 317.12632271
• Heavy Atom Count: 23
• Hydrogen Bond Acceptor Count: 5
• Hydrogen Bond Donor Count: 0
• Isomeric SMILES: COC1=CC(=CC(=C1OC)OC)/C=C/C(=O)N2CCC=CC2=O
• MDL Number: MFCD00075706
• Monoisotopic Mass: 317.12632271
• Packaging: 1 ton
• Physical State: Powder
• Rotatable Bond Count: 5
• Topological Polar Surface Area: 65.1 Ų

Custom Q&A

What is the chemical formula for PIPERLONGUMINE?

The chemical formula for PIPERLONGUMINE is C17H19NO5.

What is the molecular weight of PIPERLONGUMINE?

The molecular weight of PIPERLONGUMINE is 317.34.

At what temperature does PIPERLONGUMINE melt?

PIPERLONGUMINE melts at 124°C.

What is the solubility of PIPERLONGUMINE in DMSO?

PIPERLONGUMINE is soluble in DMSO at a concentration of ≥5mg/mL at 60°C.

How long is PIPERLONGUMINE stable for when stored as supplied?

PIPERLONGUMINE is stable for 2 years from the date of purchase when stored as supplied.

What is the main usage of PIPERLONGUMINE in terms of studying protein regulator of cytokinesis 1 (PRC1) expression?

PIPERLONGUMINE has been used to study the regulation of protein regulator of cytokinesis 1 (PRC1) expression.

What are some of the reported health benefits of PIPERLONGUMINE?

PIPERLONGUMINE has anti-cancer, anti-atherosclerotic, anxiolytic, antidiabetic, antidepressant, antibacterial, and anti-inflammatory properties.

How does PIPERLONGUMINE selectively target and kill cancer cells?

PIPERLONGUMINE selectively targets and kills cancer cells by inhibiting proteins known to regulate oxidative stress, particularly Glutathione S-transferase pi 1 (GSTP1).

What is the general description of PIPERLONGUMINE based on its properties?

PIPERLONGUMINE is an alkaloid extracted from Piper longum Linn, with various medicinal properties such as anti-cancer, anti-inflammatory, and anti-atherosclerotic effects.

What is the main target of PIPERLONGUMINE?

The main target of PIPERLONGUMINE is P450 (e.g. CYP17) and it has antifection properties.

Synthetic Use

Upstream Synthesis Route 1

• 6052-73-9

• 20069-09-4

Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 57, p. 344 - 361
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 14, p. 3925 - 3938

Upstream Synthesis Route 2

• 86-81-7

• 20069-09-4

Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 31, p. 7585 - 7593

Upstream Synthesis Route 3

• 6052-73-9
• 89652-63-1

• 20069-09-4

Reference: [1]Tetrahedron,1984,vol. 40,p. 171 - 176

Downstream Synthesis Route 1

• 20069-09-4

• 25173-72-2

Reference: [1] Phytochemistry (Elsevier), 1985, vol. 24, # 11, p. 2589 - 2592

Downstream Synthesis Route 2

• 20069-09-4

• 2466-36-6

Reference: [1]Phytochemistry,1985,vol. 24,p. 2589 - 2592
[2]RSC Advances,2018,vol. 8,p. 21407 - 21413

* For details of the synthesis route, please refer to the original source to ensure accuracy.