CAS 83327-19-9

(-)-Lariciresinol

Description:

(-)-Lariciresinol is a naturally occurring lignan, a type of polyphenolic compound found in various plants, particularly in the seeds of flax and in certain types of wood. It is characterized by its chiral nature, existing as a specific enantiomer with biological activity. The compound has a molecular formula that reflects its complex structure, which includes multiple hydroxyl groups contributing to its solubility in polar solvents. (-)-Lariciresinol is known for its antioxidant properties, which may provide health benefits by neutralizing free radicals in the body. Additionally, it has been studied for its potential anti-cancer and anti-inflammatory effects, making it of interest in pharmacological research. The compound's CAS number, 83327-19-9, is a unique identifier that facilitates its identification in scientific literature and databases. Overall, (-)-Lariciresinol exemplifies the diverse roles that natural products can play in both ecology and human health.

Formula: C₂₀H₂₄O₆

InChI: InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3/t14-,15-,20+/m1/s1

InChI key: InChIKey=MHXCIKYXNYCMHY-SXGZJXTBSA-N

SMILES: C(O)[C@H]1[C@@H](OC[C@H]1CC2=CC(OC)=C(O)C=C2)C3=CC(OC)=C(O)C=C3

Synonyms:

• (2R,3S,4S)-Tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-furanmethanol
• 3-Furanmethanol, tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-, (2R,3S,4S)-
• (-)-Lariciresinol
• 3-Furanmethanol, tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-, [2R-(2α,3β,4β)]-

(-)-Lariciresinol

CAS: 83327-19-9

Lariciresinol is a natural compound that has been shown to have antioxidative properties and inhibit the growth of cancer cells in vitro. It has also been shown to reduce the metastatic potential of colorectal cancer cells by inhibiting fatty acid synthesis. Lariciresinol has synergistic effects when combined with other natural compounds, such as resveratrol, for example. This compound inhibits the proliferation of cancer cells by inducing apoptosis through a multivariate logistic regression analysis. The mechanism of lariciresinol-mediated apoptosis includes inhibition of transcriptional regulation and mitochondrial membrane potential, which leads to an increase in reactive oxygen species (ROS) and reactive nitrogen species (RNS). Lariciresinol also inhibits bacterial growth by binding to DNA gyrase and topoisomerase IV and interfering with transcription through RNA polymerase.

Formula: C₂₀H₂₄O₆

Purity: Min. 95%

Molecular weight: 360.4 g/mol

Ref: 3D-IDA32719