ESTRAGOLE (CED0006475)

Record Information
Version1.0
Creation Date2016-05-19 02:03:24 UTC
Update Date2026-08-17 23:42:33 UTC
Accession NumberCHEM005535
Identification
Common NameESTRAGOLE
ClassSmall Molecule
Description
Estragole is an organic compound with the chemical formula C10H12O and an average molecular weight of 148.20 g/mol. ESTRAGOLE belongs to the anisoles, a subclass of phenol ethers within the organic compounds. In industrial applications, it is utilized as a fragrance, as well as a flavouring and nutrient. The compound is found in or released from 31 recorded sources across multiple sectors. Within the energy, oil and gas sector, it is used in lubricants, while the healthcare, pharmaceuticals and veterinary products sector utilizes it in medical devices. In textiles, leather and furnishings, it is associated with carpets, rugs, and synthetic textiles. It is present in food, food processing and cookware through food contact materials, food packaging, food preservation, and the preparation of vinegar. Household cleaning and consumer products include bleaching agents, perfumes within detergents and soaps, pipe accessories, cigar cigarettes, other smoking requisites, and three additional sources. Electrical and electronic equipment sources include batteries, capacitors, printed circuit boards, cell phones, wires and cables, and seven others. Additionally, it is found in three other sectors. Regarding plastics, estragole is present in polyethylene terephthalate and is released in polypropylene and low-density polyethylene. Recorded exposure routes for the compound include oral, inhalation, and touch.
Contaminant Type
  • PFAS
  • Phytotoxin
Chemical Structure
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 Mass148.202 g/mol
Monoisotopic Mass148.089 g/mol
CAS Registry Number140-67-0
IUPAC Name1-methoxy-4-(prop-2-en-1-yl)benzene
Traditional Nametarragon
SMILESCOC1=CC=C(CC=C)C=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.075 g/LALOGPS
logP3.23ALOGPS
logP2.91ChemAxon
logS-3.3ALOGPS
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
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0002-6900000000-8e0b04a96054353ba4d2Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0002-5900000000-926e28a4944e333f20a8Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0002-3900000000-fcf899888322560675f8Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0002-6900000000-8e0b04a96054353ba4d2Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0002-5900000000-926e28a4944e333f20a8Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0002-3900000000-fcf899888322560675f8Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-05cs-3900000000-15f67266c369bb73d449Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-9300000000-ed4cfbbd9e08d2cee0adNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0900000000-3765ce70f44412b9c202Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-e86d0a9f461d702ad87dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0900000000-6115b055d0ac87df694eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-2900000000-8be4c2f5dd1b59c563a8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uyl-9800000000-da4984de313826c7d325Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0900000000-590e344336c3b35d9738Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0900000000-85e1e245e010ba27ce2aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-3900000000-c9c3734a65e1844d7276Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dj-1900000000-3370bab5911072db0adfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dm-5900000000-2c944ec1b9ce38d95a4eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9100000000-23d4baf27aa3941828a2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0900000000-c2f74e33d816bec66aa0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0900000000-7512c83d9a8de7a2b2bbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a59-2900000000-fe719bda7b98ff0571f7Not AvailableView Spectrum
MSMS Spectrumsplash10-0002-6900000000-67d45b594760b36935dfNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1366.0Log mg/kg[770:2400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
10InsecticidesAgriculture & land managementNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
233BrushesPersonal care & cosmeticsNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
494Food contact materialsFood, food processing & cookwareNot Available
496FencingBuilding & ConstructionNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
663Sanitary EquipmentWastewater, sanitation & biosolidsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Cannabinoid receptor 2 structureClick to view 3D structureCannabinoid receptor 2P34972HumansPredicted (SEA)28.7264
Click to view 3D structureInward rectifier potassium channel 2P35561Mus musculusPredicted (SEA)2.56902
Polyunsaturated fatty acid 5-lipoxygenase structureClick to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP09917HumansPredicted (SEA)36.3556
Click to view 3D structureProstaglandin G/H synthase 1P05979Ovis ariesPredicted (SEA)14.1686
Click to view 3D structureProstaglandin G/H synthase 2P79208Ovis ariesPredicted (SEA)4.20386
Click to view 3D structureAryl hydrocarbon receptorO02747Oryctolagus cuniculusPredicted (SEA)3.58106
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)205.211
Cannabinoid receptor 1 structureClick to view 3D structureCannabinoid receptor 1P21554HumansPredicted (SEA)75.5916
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)322.841
Cytochrome P450 1B1 structureClick to view 3D structureCytochrome P450 1B1Q16678HumansPredicted (SEA)43.1285
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)253.633
Cytochrome P450 1A1 structureClick to view 3D structureCytochrome P450 1A1P04798HumansPredicted (SEA)41.3379
Click to view 3D structureTransient receptor potential cation channel subfamily A member 1Q6RI86Rattus norvegicusPredicted (SEA)14.2464
Transient receptor potential cation channel subfamily V member 1 structureClick to view 3D structureTransient receptor potential cation channel subfamily V member 1Q8NER1HumansPredicted (SEA)62.0458
Prostaglandin G/H synthase 2 structureClick to view 3D structureProstaglandin G/H synthase 2P35354HumansPredicted (SEA)122.457
Click to view 3D structure5-hydroxytryptamine receptor 2BP30994Rattus norvegicusPredicted (SEA)24.8339
Click to view 3D structureSigma non-opioid intracellular receptor 1Q60492Cavia porcellusPredicted (SEA)289.132
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)256.591
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)652.376
Click to view 3D structureAmine oxidase [flavin-containing] AP21396Rattus norvegicusPredicted (SEA)55.2729
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)583.091
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)824.89
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)387.767
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)130.164
Histone deacetylase 8 structureClick to view 3D structureHistone deacetylase 8Q9BY41HumansPredicted (SEA)471.066
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0034121
FooDB IDFDB012392
Phenol Explorer ID649
KNApSAcK IDC00002740
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID13850247
ChEBI IDNot Available
PubChem Compound ID8815
Kegg Compound IDC10452
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
21. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.