Tetramethoxyallylbenzene

Tetramethoxyallylbenzene
Names
IUPAC name
1,2,3,4-tetramethoxy-5-prop-2-enylbenzene
Preferred IUPAC name
1,2,3,4-Tetramethoxy-5-(prop-2-en-1-yl)benzene
Identifiers
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C13H18O4/c1-6-7-9-8-10(14-2)12(16-4)13(17-5)11(9)15-3/h6,8H,1,7H2,2-5H3 checkY
    Key: HRAXJWRHSUTMCS-UHFFFAOYSA-N checkY
Properties
C13H18O4
Molar mass 238.283 g·mol−1
Appearance Solid
Melting point 25 °C (77 °F; 298 K)
Boiling point 307 to 309 °C (585 to 588 °F; 580 to 582 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,3,4,5-Tetramethoxyallylbenzene also known as allyltetramethoxybenzene (or 1-allyl-2,3,4,5-tetramethoxybenzene), as well as methoxyelemicin, it is a phenylpropene, a natural organic compound found in the essential oils of several plant species, used as a precursor in the chemical synthesis of 2,3,4,5-tetramethoxyamphetamine.

Tetramethoxyallylbenzene is found in parsley essential oil at a concentration of 4%–13%, along with apiole and myristicin. The primary source is the leaf essential oil of the plant Polyalthia johnsonii, from which 79% of tetramethoxyallylbenzene was isolated along with elemicin. Tetramethoxyallylbenzene was detected in the essential oil of Heracleum persicum. It was found in varying amounts depending on the plant's development stage: it was detected at 0.7 ± 0.1% during the vegetative stage, reached a maximum of 3.0 ± 0.3% during the full flowering stage, and was found in trace amounts during the flower bud and early seed development stages.

See also

References

  1. ↑ Nouioura, Ghizlane; El Fadili, Mohamed; El Hachlafi, Naoufal; Abuelizz, Hatem A.; Elidrissi, Ahmed Elfallaki; Ferioun, Mohamed; Soulo, Najoua; Er-Rahmani, Sara; Lyoussi, Badiaa; Derwich, Elhoussine (2024). "Petroselinum crispum L., essential oil as promising source of bioactive compounds, antioxidant, antimicrobial activities: In vitro and in silico predictions". Heliyon. 10 (8) e29520. Bibcode:2024Heliy..1029520N. doi:10.1016/j.heliyon.2024.e29520. ISSN 2405-8440. PMC 11040043. PMID 38660278.
  2. ↑ Živković, Jelena; Petrović, Jovana; El Fadili, Mohamed; Pljevljakušić, Dejan; Lebrazi, Sara; Stojković, Dejan; Šavikin, Katarina; Fadil, Mouhcine (2026-02-12). "Optimizing Antibacterial Essential Oil Blends from Helichrysum plicatum, Petroselinum crispum, and Origanum vulgare for Dairy Preservation: Mixture Design and In Silico Analysis". Foods. 15 (4). Basel, Switzerland: 675. doi:10.3390/foods15040675. ISSN 2304-8158. PMC 12939056. PMID 41750865.
  3. ↑ Mahdi, Ismail; Imbimbo, Paola; Annaz, Hassan; Bakrim, Widad Ben; Sahri, Nihad; Alaoui, Asmae; Monti, Daria Maria; Sobeh, Mansour (2024). "Profiling of Petroselinum sativum (mill.) fuss phytoconstituents and assessment of their biocompatibility, antioxidant, anti-aging, wound healing, and antibacterial activities". Frontiers in Nutrition. 11 1338482. doi:10.3389/fnut.2024.1338482. ISSN 2296-861X. PMC 10948610. PMID 38505264.
  4. ↑ Fusani, Pietro; Biazzi, Elisa; Mella, Mariella; Doria, Filippo; Tava, Aldo (2025). "The flavonoids and oil composition of parsley [Petroselinum crispum (Mill) Nyman] fruits". Journal of Food Composition and Analysis. 140 107288. doi:10.1016/j.jfca.2025.107288. ISSN 0889-1575.
  5. ↑ Brophy, Joseph J.; Fookes, Christopher J.R.; House, Alan P.N. (1992). "The Leaf Essential Oil ofHaplostichanthus johnsoniiF. Muell". Journal of Essential Oil Research. 4 (3): 315–316. doi:10.1080/10412905.1992.9698072. ISSN 1041-2905.
  6. ↑ Hazrati, Saeid; Mollaei, Saeed; Rabbi Angourani, Hossein; Hosseini, Seyyed Jaber; Sedaghat, Mojde; Nicola, Silvana (2020). "How do essential oil composition and phenolic acid profile of Heracleum persicum fluctuate at different phenological stages?". Food Science & Nutrition. 8 (11): 6192–6206. doi:10.1002/fsn3.1916. ISSN 2048-7177. PMC 7684603. PMID 33282270.