CAS 20307-83-9

(-)-β-Sesquiphellandrene

Description:

(-)-β-Sesquiphellandrene is a naturally occurring sesquiterpene, characterized by its complex structure and unique properties. It is primarily found in various essential oils and contributes to the aroma of certain plants. This compound is known for its hydrophobic nature, making it insoluble in water but soluble in organic solvents. Its molecular structure features multiple rings and double bonds, which are typical of sesquiterpenes, contributing to its reactivity and potential biological activity. (-)-β-Sesquiphellandrene exhibits a characteristic odor, often described as woody or earthy, and is used in the fragrance industry. Additionally, it may possess antimicrobial and insecticidal properties, making it of interest in agricultural applications. The compound's stereochemistry, indicated by the prefix "(-)", denotes its specific optical activity, which can influence its interactions in biological systems. Overall, (-)-β-Sesquiphellandrene is a significant compound in both natural product chemistry and industrial applications, reflecting the diverse roles of terpenes in nature and commerce.

Formula: C₁₅H₂₄

InChI: InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,10,14-15H,3,5,7,9,11H2,1-2,4H3/t14-,15+/m0/s1

InChI key: InChIKey=PHWISBHSBNDZDX-LSDHHAIUSA-N

SMILES: [C@@H](CCC=C(C)C)(C)[C@]1(CCC(=C)C=C1)[H]

Synonyms:

• β-Sesquiphellandrene
• Cyclohexene, 3-[(1S)-1,5-dimethyl-4-hexenyl]-6-methylene-, (3R)-
• Cyclohexene, 3-(1,5-dimethyl-4-hexenyl)-6-methylene-, [S-(R*,S*)]-
• 2-Heptene, 2-methyl-6-(4-methylene-2-cyclohexen-1-yl)-, (1′R,6S)-(-)-
• Cyclohexene, 3-[(1S)-1,5-dimethyl-4-hexen-1-yl]-6-methylene-, (3R)-

(−)-β-Sesquiphellandrene

CAS: 20307-83-9

Formula: C₁₅H₂₄

Color and Shape: Liquid

Molecular weight: 204.3511

Ref: IN-DA0028O6

(−)-β-Sesquiphellandrene

CAS: 20307-83-9

(–)-β-Sesquiphellandrene, a sesquiterpene identified in Z. officinale, exhibits antiviral and anticancer properties. It effectively inhibits rhinovirus IB virus replication in a plaque reduction assay with an IC50 of 0.44 µM. Additionally, at a concentration of 10 µM, it demonstrates cytotoxicity to HCT116 cells.

Formula: C₁₅H₂₄

Color and Shape: Solid

Molecular weight: 204.35

Ref: TM-TN7506

(-)-β-Sesquiphellandrene

CAS: 20307-83-9

Formula: C₁₅H₂₄

Molecular weight: 204.36

Ref: 4Z-T-290011

(-)-β-Sesquiphellandrene

Controlled Product

CAS: 20307-83-9

Applications (-)-β-Sesquiphellandrene are found in Tanacetum vulgare plants. It is also an essential leaf and flower oils in Heracleum species.
References Clancy, M. V., et al.: Sci. Rep., 6, 38087 (2016); Usjak, L., et al.: Food Funct., 8, 278-290 (2017);

Formula: C₁₅H₂₄

Color and Shape: Colourless

Molecular weight: 204.35

Ref: TR-S280655

(-)-β-Sesquiphellandrene-d2,13C

Controlled Product

CAS: 20307-83-9

Formula: CC₁₄D₂H₂₂

Color and Shape: Neat

Molecular weight: 207.356

Ref: TR-S280657