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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:55:00 UTC
Update Date2021-10-13 06:38:54 UTC
HMDB IDHMDB0034121
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 a sweet, alcohol, and anise tasting compound. 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.
Structure
Data?1563862514
Synonyms
ValueSource
MethylchavicolKegg
4-AllylanisoleMeSH
Methyl chavicolMeSH
p-AllylanisoleMeSH
1-Allyl-4-methoxybenzeneHMDB
1-Methoxy-4-(2-propen-1-yl)-benzeneHMDB
1-Methoxy-4-(2-propen-1-yl)benzeneHMDB
1-Methoxy-4-(2-propenyl)-benzeneHMDB
1-Methoxy-4-(2-propenyl)benzene, 9ciHMDB
1-Methoxy-4-prop-2-enylbenzeneHMDB
3-(p-Methoxyphenyl)propeneHMDB
4-Allyl-1-methoxybenzeneHMDB
4-AllylmethoxybenzeneHMDB
4-MethoxyallylbenzeneHMDB
Benzene, 1-methoxy, 4-prop-2-enylHMDB
BENZENE,1-allyl,4-methoxy methylchavicolHMDB
Chavicol methyl etherHMDB
Chavicyl methyl etherHMDB
EsdragolHMDB
EsdragoleHMDB
EsdragonHMDB
EstragolHMDB
Estragol (methylchavicol)HMDB
EstragoleHMDB
Ether, P-allylphenyl methylHMDB
FEMA 2411HMDB
IsoanetholeHMDB
IsoanthetholeHMDB
Methyl chavicoleHMDB
Methyl chavicole (estragole)HMDB
Methyl-chavicolHMDB
O-Methyl-chavicolHMDB
P-Allyl-anisoleHMDB
P-AllylmethoxybenzeneHMDB
p-Allylphenyl methyl etherHMDB
p-MethoxyallylbenzeneHMDB
Para-allylanisole (estragole)HMDB
TarragonHMDB
TerragonHMDB
1-Methoxy-4-(2-propenyl)benzeneKEGG
3-(4-Methoxyphenyl)-1-propenePhytoBank
3-(4-Methoxyphenyl)propenePhytoBank
3-(p-Methoxyphenyl)-1-propenePhytoBank
EsteragolPhytoBank
EstragenolePhytoBank
O-MethylchavicolPhytoBank
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
SMILES
COC1=CC=C(CC=C)C=C1
InChI Identifier
InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H3
InChI KeyZFMSMUAANRJZFM-UHFFFAOYSA-N
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
Substituents
  • 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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point215.00 to 216.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.18 mg/mL at 25 °CNot Available
LogP3.151 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.075 g/LALOGPS
logP10(3.23) g/LALOGPS
logP10(2.91) g/LChemAxon
logS10(-3.3) 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.46431661259
DarkChem[M-H]-133.46431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-Methoxy-4-(2-propenyl)benzeneCOC1=CC=C(CC=C)C=C11705.8Standard polar33892256
1-Methoxy-4-(2-propenyl)benzeneCOC1=CC=C(CC=C)C=C11188.7Standard non polar33892256
1-Methoxy-4-(2-propenyl)benzeneCOC1=CC=C(CC=C)C=C11195.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene EI-B (Non-derivatized)splash10-0002-6900000000-8e0b04a96054353ba4d22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene EI-B (Non-derivatized)splash10-0002-5900000000-926e28a4944e333f20a82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene EI-B (Non-derivatized)splash10-0002-3900000000-fcf899888322560675f82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene EI-B (Non-derivatized)splash10-0002-6900000000-8e0b04a96054353ba4d22018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene EI-B (Non-derivatized)splash10-0002-5900000000-926e28a4944e333f20a82018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene EI-B (Non-derivatized)splash10-0002-3900000000-fcf899888322560675f82018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene GC-MS (Non-derivatized) - 70eV, Positivesplash10-05cs-3900000000-15f67266c369bb73d4492017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-6900000000-67d45b594760b36935df2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene Linear Ion Trap , negative-QTOFsplash10-03di-9300000000-ed4cfbbd9e08d2cee0ad2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene Linear Ion Trap , positive-QTOFsplash10-0002-0900000000-3765ce70f44412b9c2022017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene Linear Ion Trap , positive-QTOFsplash10-014i-0900000000-e86d0a9f461d702ad87d2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene 10V, Positive-QTOFsplash10-0002-0900000000-6115b055d0ac87df694e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene 20V, Positive-QTOFsplash10-0002-2900000000-8be4c2f5dd1b59c563a82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene 40V, Positive-QTOFsplash10-0uyl-9800000000-da4984de313826c7d3252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene 10V, Negative-QTOFsplash10-0002-0900000000-590e344336c3b35d97382016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene 20V, Negative-QTOFsplash10-0002-0900000000-85e1e245e010ba27ce2a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene 40V, Negative-QTOFsplash10-001i-3900000000-c9c3734a65e1844d72762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene 10V, Positive-QTOFsplash10-00dj-1900000000-3370bab5911072db0adf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene 20V, Positive-QTOFsplash10-00dm-5900000000-2c944ec1b9ce38d95a4e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene 40V, Positive-QTOFsplash10-004i-9100000000-23d4baf27aa3941828a22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene 10V, Negative-QTOFsplash10-0002-0900000000-c2f74e33d816bec66aa02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene 20V, Negative-QTOFsplash10-0002-0900000000-7512c83d9a8de7a2b2bb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methoxy-4-(2-propenyl)benzene 40V, Negative-QTOFsplash10-0a59-2900000000-fe719bda7b98ff0571f72021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specified
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specified
Treated celiac disease
details
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
MarkerDB IDNot Available
Good Scents IDrw1013251
References
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.. .