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Record Information
StatusDetected but not Quantified
Creation Date2012-09-11 18:55:00 UTC
Update Date2019-07-23 06:15:14 UTC
Secondary Accession Numbers
  • HMDB34121
Metabolite Identification
Common Name1-Methoxy-4-(2-propenyl)benzene
Description1-Methoxy-4-(2-propenyl)benzene, also known as methylchavicol or estragol, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. 1-Methoxy-4-(2-propenyl)benzene is an extremely weak basic (essentially neutral) compound (based on its pKa). 1-Methoxy-4-(2-propenyl)benzene is a sweet, alcohol, and anise tasting compound. Outside of the human body, 1-Methoxy-4-(2-propenyl)benzene is found, on average, in the highest concentration within a few different foods, such as anises, fennels, and sweet basils and in a lower concentration in cumins, tarragons, and parsley. 1-Methoxy-4-(2-propenyl)benzene has also been detected, but not quantified in, several different foods, such as citrus, chinese cinnamons, caraway, fats and oils, and cloves. This could make 1-methoxy-4-(2-propenyl)benzene a potential biomarker for the consumption of these foods. 1-Methoxy-4-(2-propenyl)benzene, with regard to humans, has been linked to the inborn metabolic disorder celiac disease.
1-Methoxy-4-(2-propenyl)benzene, 9ciHMDB
Benzene, 1-methoxy, 4-prop-2-enylHMDB
BENZENE,1-allyl,4-methoxy methylchavicolHMDB
Chavicol methyl etherHMDB
Chavicyl methyl etherHMDB
Estragol (methylchavicol)HMDB
Ether, p-allylphenyl methylHMDB
Methyl chavicolHMDB
Methyl chavicoleHMDB
Methyl chavicole (estragole)HMDB
p-Allylphenyl methyl etherHMDB
Para-allylanisole (estragole)HMDB
Chemical FormulaC10H12O
Average Molecular Weight148.2017
Monoisotopic Molecular Weight148.088815006
IUPAC Name1-methoxy-4-(prop-2-en-1-yl)benzene
Traditional Nametarragon
CAS Registry Number140-67-0
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
Alternative Parents
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

Route of exposure:


Biological location:


Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.18 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.075 g/LALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.81 m³·mol⁻¹ChemAxon
Polarizability16.95 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-6900000000-8e0b04a96054353ba4d2Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-5900000000-926e28a4944e333f20a8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-3900000000-fcf899888322560675f8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-6900000000-8e0b04a96054353ba4d2Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-5900000000-926e28a4944e333f20a8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-3900000000-fcf899888322560675f8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05cs-3900000000-15f67266c369bb73d449Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-9300000000-ed4cfbbd9e08d2cee0adSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0900000000-3765ce70f44412b9c202Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0900000000-e86d0a9f461d702ad87dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-6115b055d0ac87df694eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-2900000000-8be4c2f5dd1b59c563a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uyl-9800000000-da4984de313826c7d325Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-590e344336c3b35d9738Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-85e1e245e010ba27ce2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-3900000000-c9c3734a65e1844d7276Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-6900000000-67d45b594760b36935dfSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Normal Concentrations
FecesDetected but not Quantified Adult (>18 years old)Both
FecesDetected but not Quantified Children (1-13 years old)Not Specified
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
FecesDetected but not Quantified Children (1-13 years old)Not Specified
Treated celiac disease
Associated Disorders and Diseases
Disease References
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound ID649
FooDB IDFDB012392
KNApSAcK IDC00002740
Chemspider ID13850247
KEGG Compound IDC10452
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8815
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chizzola R: Composition of the essential oils from Anthriscus cerefolium var. trichocarpa and A. caucalis growing wild in the urban area of Vienna (Austria). Nat Prod Commun. 2011 Aug;6(8):1147-50. [PubMed:21922923 ]
  2. Gang DR, Wang J, Dudareva N, Nam KH, Simon JE, Lewinsohn E, Pichersky E: An investigation of the storage and biosynthesis of phenylpropenes in sweet basil. Plant Physiol. 2001 Feb;125(2):539-55. [PubMed:11161012 ]
  3. Caballero-Gallardo K, Olivero-Verbel J, Stashenko EE: Repellent activity of essential oils and some of their individual constituents against Tribolium castaneum herbst. J Agric Food Chem. 2011 Mar 9;59(5):1690-6. doi: 10.1021/jf103937p. Epub 2011 Feb 3. [PubMed:21291237 ]
  4. Orav A, Raal A, Arak E: Essential oil composition of Pimpinella anisum L. fruits from various European countries. Nat Prod Res. 2008 Feb 15;22(3):227-32. doi: 10.1080/14786410701424667. [PubMed:18266152 ]
  5. Deschamps C, Simon JE: Phenylpropanoid biosynthesis in leaves and glandular trichomes of basil (Ocimum basilicum L.). Methods Mol Biol. 2010;643:263-73. doi: 10.1007/978-1-60761-723-5_18. [PubMed:20552457 ]
  6. Teissedre PL, Waterhouse AL: Inhibition of oxidation of human low-density lipoproteins by phenolic substances in different essential oils varieties. J Agric Food Chem. 2000 Sep;48(9):3801-5. [PubMed:10995274 ]
  7. Nesslany F, Parent-Massin D, Marzin D: Risk assessment of consumption of methylchavicol and tarragon: the genotoxic potential in vivo and in vitro. Mutat Res. 2010 Feb;696(1):1-9. doi: 10.1016/j.mrgentox.2009.11.003. Epub 2009 Nov 11. [PubMed:19913108 ]
  8. Yang D, Wang F, Su J, Zeng L: [Chemical composition of essential oil in stems, leaves and flowers of Agastache rugosa]. Zhong Yao Cai. 2000 Mar;23(3):149-51. [PubMed:12575134 ]
  9. Zheljazkov VD, Cantrell CL, Tekwani B, Khan SI: Content, composition, and bioactivity of the essential oils of three basil genotypes as a function of harvesting. J Agric Food Chem. 2008 Jan 23;56(2):380-5. Epub 2007 Dec 21. [PubMed:18095647 ]
  10. Rodrigues VM, Rosa PT, Marques MO, Petenate AJ, Meireles MA: Supercritical extraction of essential oil from aniseed (Pimpinella anisum L) using CO2: solubility, kinetics, and composition data. J Agric Food Chem. 2003 Mar 12;51(6):1518-23. [PubMed:12617576 ]
  11. Bidri M, Conti M, Franetich JF, Tefit M, Mazier D, Arock M, Vouldoukis I: Fresh aromatic herbs containing methylchavicol did not exhibit the pro-oxidative effects of pure methylchavicol on a human hepatoma cell line, HepG2. Ann Pharm Fr. 2012 Sep;70(5):256-63. doi: 10.1016/j.pharma.2012.06.005. Epub 2012 Sep 3. [PubMed:23020916 ]
  12. Du Z, Clery RA, Hammond CJ: Volatiles from leaves and rhizomes of Fragrant Acorus spp. (Acoraceae). Chem Biodivers. 2008 Jun;5(6):887-95. doi: 10.1002/cbdv.200890102. [PubMed:18618386 ]
  13. Gang DR, Lavid N, Zubieta C, Chen F, Beuerle T, Lewinsohn E, Noel JP, Pichersky E: Characterization of phenylpropene O-methyltransferases from sweet basil: facile change of substrate specificity and convergent evolution within a plant O-methyltransferase family. Plant Cell. 2002 Feb;14(2):505-19. [PubMed:11884690 ]
  14. Kalantari H, Galehdari H, Zaree Z, Gesztelyi R, Varga B, Haines D, Bombicz M, Tosaki A, Juhasz B: Toxicological and mutagenic analysis of Artemisia dracunculus (tarragon) extract. Food Chem Toxicol. 2013 Jan;51:26-32. doi: 10.1016/j.fct.2012.07.052. Epub 2012 Aug 4. [PubMed:23010670 ]
  15. Martini MG, Bizzo HR, Moreira Dde L, Neufeld PM, Miranda SN, Alviano CS, Alviano DS, Leitao SG: Chemical composition and antimicrobial activities of the essential oils from Ocimum selloi and Hesperozygis myrtoides. Nat Prod Commun. 2011 Jul;6(7):1027-30. [PubMed:21834250 ]
  16. Vassao DG, Gang DR, Koeduka T, Jackson B, Pichersky E, Davin LB, Lewis NG: Chavicol formation in sweet basil (Ocimum basilicum): cleavage of an esterified C9 hydroxyl group with NAD(P)H-dependent reduction. Org Biomol Chem. 2006 Jul 21;4(14):2733-44. Epub 2006 Jun 9. [PubMed:16826298 ]
  17. Nascimento JC, Barbosa LC, Paula VF, David JM, Fontana R, Silva LA, Franca RS: Chemical composition and antimicrobial activity of essential oils of Ocimum canum Sims. and Ocimum selloi Benth. An Acad Bras Cienc. 2011 Sep;83(3):787-99. [PubMed:21969960 ]
  18. Yousif AN, Scaman CH, Durance TD, Girard B: Flavor volatiles and physical properties of vacuum-microwave- and air-dried sweet basil (Ocimum basilicum L.). J Agric Food Chem. 1999 Nov;47(11):4777-81. [PubMed:10552889 ]
  19. Lopez SB, Lopez ML, Aragon LM, Tereschuk ML, Slanis AC, Feresin GE, Zygadlo JA, Tapia AA: Composition and anti-insect activity of essential oils from Tagetes L. species (Asteraceae, Helenieae) on Ceratitis capitata Wiedemann and Triatoma infestans Klug. J Agric Food Chem. 2011 May 25;59(10):5286-92. doi: 10.1021/jf104966b. Epub 2011 Apr 15. [PubMed:21469658 ]
  20. Hamm S, Bleton J, Connan J, Tchapla A: A chemical investigation by headspace SPME and GC-MS of volatile and semi-volatile terpenes in various olibanum samples. Phytochemistry. 2005 Jun;66(12):1499-514. [PubMed:15922374 ]
  21. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .