2-Methoxy-4-propylphenol (T3D3230)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-07-30 17:56:36 UTC
Update Date2014-12-24 20:26:01 UTC
Accession NumberT3D3230
Identification
Common Name2-Methoxy-4-propylphenol
ClassSmall Molecule
Description2-Methoxy-4-propylphenol is a flavouring ingredient 2-Methoxy-4-propylphenol belongs to the family of Methoxyphenols and Derivatives. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
Compound Type
  • Ether
  • Food Toxin
  • Fragrance Toxin
  • Household Toxin
  • Lachrymator
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
(4-Hydroxy-3-methoxyphenyl)propane
1-(4-Hydroxy-3-methoxyphenyl)propane
1-Propyl-3-methoxy-4-hydroxybenzene
2-Methoxy-4-(1-propyl)phenol
2-Methoxy-4-N-propylphenol
2-Methoxy-4-propyl-Phenol
2-Methoxy-4-propylphenol (p-propylguaiacol)
2-Methoxy-4-propylphenol, 9CI
4-Hydroxy-3-methoxypropylbenzene
4-Propyl-2-methoxyphenol
4-Propyl-2-methoxyphenol (4-propylguaiacol)
4-Propyl-Guaiacol
4-Propyl-O-methoxyphenol
4-Propylguaiacol
5-Propyl-O-hydroxyanisole
Cerulignol
Coerulignol
Dihydroeugenol
Eugenol dihydro
Guaiacylpropane
P-N-Propylguaiacol
P-Propylguaiacol
Phenol, 4-propyl, 2-methoxy
Propylguaiacol
Chemical FormulaC10H14O2
Average Molecular Mass166.217 g/mol
Monoisotopic Mass166.099 g/mol
CAS Registry Number2785-87-7
IUPAC Name2-methoxy-4-propylphenol
Traditional Namephenol, 2-methoxy-4-propyl-
SMILESCCCC1=CC(OC)=C(O)C=C1
InChI IdentifierInChI=1S/C10H14O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h5-7,11H,3-4H2,1-2H3
InChI KeyInChIKey=PXIKRTCSSLJURC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenylpropane
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless clear liquid (3).
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.89 g/LALOGPS
logP2.87ALOGPS
logP2.91ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.75 m³·mol⁻¹ChemAxon
Polarizability18.78 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f9i-2900000000-51ab1f04188439c1f6632016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-8690000000-12ed44035d829a9f7ff42017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-646bc22bdc72fdc8df592016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-60aaf34920a151b1ce532016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9200000000-bb7502bb9a87017830952016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-397c386607b8c61e83b42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-a72a438f24be53c7f6402016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mn-4900000000-c92b92d205fe2182af192016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-349584a3f625d5b5807f2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-93843d8e2b9d8bf8ec662021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06dl-9600000000-470288177a1f018791d92021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-516a0ffed3b219171b902021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016v-5900000000-b4131d503f35ea1463862021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-005c-9100000000-0fc7a6cb0cf0bac4a9062021-09-22View Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-7900000000-972dcdcdab5502fe481a2014-09-20View Spectrum
Toxicity Profile
Route of ExposureDermal (3, 1) ; eye contact (3, 1) ; inhalation (3, 1) ; oral (3, 1)
Mechanism of ToxicityDihydroeugenol may cause allergic contact dermatitis via two different mechanisms: The poison ivy and the phenolic radical mechanisms (1).
MetabolismNot Available
Toxicity ValuesLD50: 2000.00 mg/kg (Oral, Mouse) (3) LD50: 2600.00 mg/kg (Oral, Rat) (3) LD50: 310.00 mg/kg (Dermal, Rabbit) (3)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (5)
Uses/SourcesUsed as flavoring and fragrance ingredient (3).
Minimum Risk LevelNot Available
Health EffectsDermatitis (1).
SymptomsChoking, drowsiness, and respiratory disruptions after inhalation; irritation, and reddening of the eyes; skin irritation; queasiness, and stomach aches following ingestion(3).
TreatmentTreat symptomatically and supportively. Do not induce vomiting. (4)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB32135
PubChem Compound ID17739
ChEMBL IDNot Available
ChemSpider ID16763
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDCPD-10489
CTD IDNot Available
Stitch IDDihydroeugenol
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3230.pdf
General References
  1. Barratt MD, Basketter DA: Possible origin of the skin sensitization potential of isoeugenol and related compounds. (I). Preliminary studies of potential reaction mechanisms. Contact Dermatitis. 1992 Aug;27(2):98-104. [1395636 ]
  2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  3. The Good Scents Company (2009). Material Safety Data Sheet for Dihydroeugenol. [Link]
  4. Quest International (1999). Material Safety Data Sheet for Dihydroeugenol. [Link]
  5. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Transient receptor potential cation channel subfamily A member 1
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]