Dillapiole (also spelled dillapiol) is an allylbenzene found in certain chemotypes of dill seed, but usually absent from common dill seed.

Dillapiole is an extremely potent natural inhibitor of CYP3A4 in vitro with an IC50 of 16.7 µM.[1] Another test determined an in vitro IC50 value of less than 0.5 µM. [8]

Dillapiole increased the potency of gedunin and 7-methoxygedunin in vivo in male mice. This increase in potency was believed to be caused by inhibition of CYP3A4. [7]

Dillapiole's ability to inhibit CYP3A4 appears to be untested in humans.

Natural Sources

Plant Origin Part Contents of Essential Oil
Apium nodiflorum Italy 70.8% [2]
Apium nodiflorum Portugal 22.5% [2]
Black caraway fruit 44.6% [3]
Dill CT dillapiole seeds 20%
Piper guineense Leaves 44.8% [4]
Piper aduncum North Brazil 35-90% [5], 45.9%[9]
Bunium Cylindricum (Boiss. et Hohen.) Drude Fruit 11% [6]

Chemical Properties

Synonyms: Dillapiol; Dillapiole; Dill apiole; Dill apiol; Apiole (dill)
PubChem Compound ID: 10231
Molecular Weight: 222.23716 [g/mol]
Molecular Formula: C12H14O4
XLogP3-AA: 2.7
H-Bond Donor: 0
H-Bond Acceptor: 4
IUPAC Name: 4,5-dimethoxy-6-prop-2-enyl-1,3-benzodioxole
InChI: InChI=1S/C12H14O4/c1-4-5-8-6-9-11(16-7-15-9)12(14-3)10(8)13-2/h4,6H,1,5,7H2,2-3H3
Canonical SMILES: COC1=C(C2=C(C=C1CC=C)OCO2)OC

See Also

1. Tepy Usia, Hiroshi Iwata, Akira Hiratsuka, Tadashi Watabe, Shigetoshi Kadota, and Yasuhiro Tezuka;
Sesquiterpenes and Flavonol Glycosides from Zingiber aromaticum and Their CYP3A4 and CYP2D6 Inhibitory Activities;Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, 2630-Sugitani, Toyama 930-0194, Japan.; J. Nat. Prod., 2004, 67 (7), pp 1079–1083; DOI: 10.1021/np030556a; Publication Date (Web): June 17, 2004 (Download Attached PDF Document)
2. Maxia A, Falconieri D, Piras A, Porcedda S, Marongiu B, Frau MA, Gonçalves MJ, Cabral C, Cavaleiro C, Salgueiro L.;
Chemical composition and antifungal activity of essential oils and supercritical CO2 extracts of Apium nodiflorum (L.) Lag; Mycopathologia. 2012 Jul;174(1):61-7. doi: 10.1007/s11046-011-9519-2. Epub 2012 Jan 12.
3. Kapoor IP, Singh B, Singh G, De Heluani CS, De Lampasona MP, Catalan CA.;
Chemistry and antioxidant activity of essential oil and oleoresins of black caraway (Carum bulbocastanum) fruits: Part 69. Chemistry Department, D.D.U. Gorakhpur University, Gorakhpur-273009, India.; J Sci Food Agric. 2010 Feb;90(3):385-90. doi: 10.1002/jsfa.3824.
ESSENTIAL OILS FROM FOUR PIPER SPECIES Phytochemistry Vol. 49, No. 7, pp. 2019±2023, 1998; PII: S0031-9422(98)00391-4
5. de Almeida RR, Souto RN, Bastos CN, da Silva MH, Maia JG.;
Chemical variation in Piper aduncum and biological properties of its dillapiole-rich essential oil; Chem Biodivers. 2009 Sep;6(9):1427-34. doi: 10.1002/cbdv.200800212
6. Shakhnoza S. Azimova, Anna I. Glushenkova, Valentina I. Vinogradova;
Lipids, Lipophilic Components and Essential Oils from Plant Sources; Yunusov Institute of Plant Substances, Tashkent, Uzbekistan; Springer, 2012; ISBN 0857293230, 9780857293237
7. Phytochemical discovery of antifeedant, antimicrobial and antirnalarial principles
Semir Omar; University of Ottawa; 2000; (Download Attached PDF Document)
8. Phytomedicine. 2000 Jul;7(4):273-82.
An in vitro evaluation of human cytochrome P450 3A4 inhibition by selected commercial herbal extracts and tinctures. Budzinski JW, Foster BC, Vandenhoek S, Arnason JT; Ottawa-Carleton Institute of Biology, University of Ottawa, Ontario, Canada. PubMed PMID: 10969720
9. Environ Toxicol Pharmacol. 2009 Jan;27(1):39-48. doi: 10.1016/j.etap.2008.08.002. Epub 2008 Aug 19.
Bioactivities of Piper aduncum L. and Piper obliquum Ruiz & Pavon (Piperaceae) essential oils from Eastern Ecuador. Guerrini A, Sacchetti G, Rossi D, Paganetto G, Muzzoli M, Andreotti E, Tognolini M, Maldonado ME, Bruni R.; Dip. di Biologia ed Evoluzione, Sez. Risorse Agrotecnologiche e Farmaceutiche AgriUnife, Università degli Studi di Ferrara, Italy. PubMed PMID: 21783920
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