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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:48:03 UTC

Update Date

2023-02-21 17:21:38 UTC

HMDB ID

HMDB0032135

Secondary Accession Numbers

HMDB32135

Metabolite Identification

Common Name

2-Methoxy-4-propylphenol

Description

2-Methoxy-4-propylphenol 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 a sweet, allspice, and anise tasting compound. Based on a literature review very few articles have been published on 2-Methoxy-4-propylphenol.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 06-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-14         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   12                                                            
CONECT    3    1    4                                                       
CONECT    4    3    8                                                       
CONECT    5    6    8                                                       
CONECT    6    5    9                                                       
CONECT    7    8   10                                                       
CONECT    8    4    5    7                                                  
CONECT    9    6   10   11                                                  
CONECT   10    7    9   12                                                  
CONECT   11    9                                                            
CONECT   12    2   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

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

2785-87-7

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

Physiological effect

Health effect

Observation

Drowsiness (HMDB: HMDB0032135)
Skin irritation (HMDB: HMDB0032135)

Organoleptic effect

Odor

Taste

Sweet

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0032135)
Cell membrane (HMDB: HMDB0032135)

Route of exposure

Parenteral

Enteral

Ingestion (HMDB: HMDB0032135)

Source

Endogenous

Endogenous (HMDB: HMDB0032135)

Exogenous

Food

Food (HMDB: HMDB0032135)

Exogenous (HMDB: HMDB0032135)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0032135)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	125.00 to 126.00 °C. @ 14.00 mm Hg	The Good Scents Company Information System
Water Solubility	228 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.390	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.89 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.331	31661259
DarkChem	[M-H]-	135.831	31661259
DeepCCS	[M+H]+	140.182	30932474
DeepCCS	[M-H]-	136.353	30932474
DeepCCS	[M-2H]-	173.895	30932474
DeepCCS	[M+Na]+	149.434	30932474
AllCCS	[M+H]+	136.4	32859911
AllCCS	[M+H-H2O]+	131.9	32859911
AllCCS	[M+NH4]+	140.5	32859911
AllCCS	[M+Na]+	141.7	32859911
AllCCS	[M-H]-	138.4	32859911
AllCCS	[M+Na-2H]-	139.6	32859911
AllCCS	[M+HCOO]-	141.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.89 minutes	32390414
Predicted by Siyang on May 30, 2022	13.8867 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.57 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1891.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	432.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	175.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	265.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	286.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	666.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	609.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1276.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	469.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1288.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	389.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	436.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	400.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	307.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	26.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methoxy-4-propylphenol	CCCC1=CC(OC)=C(O)C=C1	2095.1	Standard polar	33892256
2-Methoxy-4-propylphenol	CCCC1=CC(OC)=C(O)C=C1	1335.4	Standard non polar	33892256
2-Methoxy-4-propylphenol	CCCC1=CC(OC)=C(O)C=C1	1377.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Methoxy-4-propylphenol,1TMS,isomer #1	CCCC1=CC=C(O[Si](C)(C)C)C(OC)=C1	1435.7	Semi standard non polar	33892256
2-Methoxy-4-propylphenol,1TBDMS,isomer #1	CCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1	1679.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-4-propylphenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f9i-2900000000-51ab1f04188439c1f663	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-4-propylphenol GC-MS (1 TMS) - 70eV, Positive	splash10-00di-8690000000-12ed44035d829a9f7ff4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-4-propylphenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-7900000000-972dcdcdab5502fe481a	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-propylphenol 10V, Positive-QTOF	splash10-014i-0900000000-646bc22bdc72fdc8df59	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-propylphenol 20V, Positive-QTOF	splash10-014i-2900000000-60aaf34920a151b1ce53	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-propylphenol 40V, Positive-QTOF	splash10-0f6x-9200000000-bb7502bb9a8701783095	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-propylphenol 10V, Negative-QTOF	splash10-014i-0900000000-397c386607b8c61e83b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-propylphenol 20V, Negative-QTOF	splash10-014i-0900000000-a72a438f24be53c7f640	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-propylphenol 40V, Negative-QTOF	splash10-05mn-4900000000-c92b92d205fe2182af19	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-propylphenol 10V, Negative-QTOF	splash10-014i-0900000000-349584a3f625d5b5807f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-propylphenol 20V, Negative-QTOF	splash10-014i-0900000000-93843d8e2b9d8bf8ec66	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-propylphenol 40V, Negative-QTOF	splash10-06dl-9600000000-470288177a1f018791d9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-propylphenol 10V, Positive-QTOF	splash10-014i-0900000000-516a0ffed3b219171b90	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-propylphenol 20V, Positive-QTOF	splash10-016v-5900000000-b4131d503f35ea146386	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-4-propylphenol 40V, Positive-QTOF	splash10-005c-9100000000-0fc7a6cb0cf0bac4a906	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1017131

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2-Methoxy-4-propylphenol (HMDB0032135)

MOL for HMDB0032135 (2-Methoxy-4-propylphenol)

3D MOL for HMDB0032135 (2-Methoxy-4-propylphenol)

3D SDF for HMDB0032135 (2-Methoxy-4-propylphenol)

3D-SDF for HMDB0032135 (2-Methoxy-4-propylphenol)

PDB for HMDB0032135 (2-Methoxy-4-propylphenol)

3D PDB for HMDB0032135 (2-Methoxy-4-propylphenol)

SMILES for HMDB0032135 (2-Methoxy-4-propylphenol)

INCHI for HMDB0032135 (2-Methoxy-4-propylphenol)

Structure for HMDB0032135 (2-Methoxy-4-propylphenol)

3D Structure for HMDB0032135 (2-Methoxy-4-propylphenol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra