Cannabis Compound Database: Showing Compound Card for 2-Methoxy-4-propylphenol (CDB006385)

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Record Information

Version

1.0

Created at

2021-01-13 17:43:52 UTC

Updated at

2021-01-13 17:43:54 UTC

CannabisDB ID

CDB006385

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

2-Methoxy-4-propylphenol

Description

2-Methoxy-4-propylphenol, also known as dihydroeugenol, 4-propyl-2-methoxyphenol or 4-propylguaiacol, 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. 2-Methoxy-4-propylphenol is one of several structural isomers of propylmethoxyphenol wherein the propyl and methoxy groups are substituted at different positions of phenol. 2-Methoxy-4-propylphenol exists as a clear, colorless liquid that is water soluble. It has a spicey, sharp, sweet, allspice odor and a spicy peppery or clove like taste. 2-Methoxy-4-propylphenol is found naturally in a number of foods including beer, brandy, gruyere cheese, fish, pork, rum, sherry, tea and whiskey. It is also found in Bordeaux windes liquid smoke, karanda fruit and oregano. 2-Methoxy-4-propylphenol is widely used as a food additive and a perfuming agent in cosmetics and household products. It is used to enhance the profile of smoke flavors, clove, spicy nuances for cinnamon and pepper, vanilla, and fruit nuances. Traces (0.5-1%) can be found in many consumer products such as candles, detergent, shampoo, softeners and soap. 2-Methoxy-4-propylphenol is also used as a pheromone for the Northern corn rootworm. It has also been shown to have anti-oxidant effects and inhibits lipid peroxidation and scanvenges superoxide and hydroxyl radicals (PMID: 11045452 ). Propylmethoxyphenols are found in marijuana (cannabis) smoke. 2-Methoxy-4-propylphenol is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(4-Hydroxy-3-methoxyphenyl)propane	HMDB
1-(4-Hydroxy-3-methoxyphenyl)propane	HMDB
1-Propyl-3-methoxy-4-hydroxybenzene	HMDB
2-Methoxy-4-(1-propyl)phenol	HMDB
2-Methoxy-4-N-propylphenol	HMDB
2-Methoxy-4-propyl-phenol	HMDB
2-Methoxy-4-propylphenol (P-propylguaiacol)	HMDB
2-Methoxy-4-propylphenol, 9ci	HMDB
4-Hydroxy-3-methoxypropylbenzene	HMDB
4-Propyl-2-methoxyphenol	HMDB
4-Propyl-2-methoxyphenol (4-propylguaiacol)	HMDB
4-Propyl-guaiacol	HMDB
4-Propyl-O-methoxyphenol	HMDB
4-Propylguaiacol	HMDB
5-Propyl-O-hydroxyanisole	HMDB
Cerulignol	HMDB
Coerulignol	HMDB
Dihydroeugenol	HMDB
Eugenol dihydro	HMDB
Guaiacylpropane	HMDB
P-N-Propylguaiacol	HMDB
P-Propylguaiacol	HMDB
Phenol, 4-propyl, 2-methoxy	HMDB
Propylguaiacol	HMDB

Chemical Formula

C₁₀H₁₄O₂

Average Molecular Weight

166.217

Monoisotopic Molecular Weight

166.099379692

IUPAC Name

2-methoxy-4-propylphenol

Traditional Name

phenol, 2-methoxy-4-propyl-

CAS Registry Number

Not Available

SMILES

CCCC1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C10H14O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h5-7,11H,3-4H2,1-2H3

InChI Key

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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.87	ALOGPS
logP	2.91	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	10.29	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.75 m³·mol⁻¹	ChemAxon
Polarizability	18.78 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-000i-7900000000-972dcdcdab5502fe481a	2014-09-20	View Spectrum
Predicted GC-MS	2-Methoxy-4-propylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0f9i-2900000000-51ab1f04188439c1f663	Spectrum
Predicted GC-MS	2-Methoxy-4-propylphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-8690000000-12ed44035d829a9f7ff4	Spectrum
Predicted GC-MS	2-Methoxy-4-propylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-646bc22bdc72fdc8df59	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-2900000000-60aaf34920a151b1ce53	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6x-9200000000-bb7502bb9a8701783095	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-397c386607b8c61e83b4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-a72a438f24be53c7f640	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mn-4900000000-c92b92d205fe2182af19	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-349584a3f625d5b5807f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-93843d8e2b9d8bf8ec66	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06dl-9600000000-470288177a1f018791d9	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-516a0ffed3b219171b90	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-016v-5900000000-b4131d503f35ea146386	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-005c-9100000000-0fc7a6cb0cf0bac4a906	2021-09-22	View Spectrum

NMR

Type	Description		View

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0032135

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008859

KNApSAcK ID

Not Available

Chemspider ID

16763

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

17739

PDB ID

Not Available

ChEBI ID

Not Available

References

General References

Ogata M, Hoshi M, Urano S, Endo T: Antioxidant activity of eugenol and related monomeric and dimeric compounds. Chem Pharm Bull (Tokyo). 2000 Oct;48(10):1467-9. doi: 10.1248/cpb.48.1467. [PubMed:11045452 ]

Showing Compound Card for 2-Methoxy-4-propylphenol (CDB006385)

Structure for CDB006385 (2-Methoxy-4-propylphenol)