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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:38 UTC

Update Date

2023-02-21 17:22:25 UTC

HMDB ID

HMDB0032586

Secondary Accession Numbers

HMDB32586

Metabolite Identification

Common Name

3-(4-Methoxyphenyl)-2-propen-1-ol

Description

3-(4-Methoxyphenyl)-2-propen-1-ol, also known as 4-methoxycinnamyl alcohol or 3'-hydroxyanethole, belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety. Based on a literature review a significant number of articles have been published on 3-(4-Methoxyphenyl)-2-propen-1-ol.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   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   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2    3    8                                                       
CONECT    3    2    9                                                       
CONECT    4    6    9                                                       
CONECT    5    7    9                                                       
CONECT    6    4   10                                                       
CONECT    7    5   10                                                       
CONECT    8    2   11                                                       
CONECT    9    3    4    5                                                  
CONECT   10    6    7   12                                                  
CONECT   11    8                                                            
CONECT   12    1   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(e)-3-(4-Methoxyphenyl)-2-propen-1-ol	HMDB
2-Propen-1-ol, 3-(4-methoxyphenyl)- (9ci)	HMDB
3'-Hydroxyanethole	HMDB
3-(4-Methoxyphenyl)-(e)-2-propen-1-ol	HMDB
3-(p-Methoxyphenyl)-2-propen-1-ol	HMDB
4-Methoxycinnamyl alcohol	HMDB
Ghl.PD_Mitscher_leg0.196	HMDB
p-Methoxycinnamyl alcohol	HMDB
trans-4-Methoxycinnamyl alcohol	HMDB

Chemical Formula

C₁₀H₁₂O₂

Average Molecular Weight

164.2011

Monoisotopic Molecular Weight

164.083729628

IUPAC Name

(2E)-3-(4-methoxyphenyl)prop-2-en-1-ol

Traditional Name

(2E)-3-(4-methoxyphenyl)prop-2-en-1-ol

CAS Registry Number

53484-50-7

SMILES

COC1=CC=C(\C=C\CO)C=C1

InChI Identifier

InChI=1S/C10H12O2/c1-12-10-6-4-9(5-7-10)3-2-8-11/h2-7,11H,8H2,1H3/b3-2+

InChI Key

NYICIIFSBJOBKE-NSCUHMNNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamyl alcohols

Sub Class

Not Available

Direct Parent

Cinnamyl alcohols

Alternative Parents

Substituents

Cinnamyl alcohol
Anisole
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ether
Primary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenylpropanoid (CHEBI:86916 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032586)
Cytoplasm (HMDB: HMDB0032586)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032586)

Source

Endogenous

Endogenous (HMDB: HMDB0032586)

Plant

Plant (HMDB: HMDB0032586)

Exogenous

Food

Food (HMDB: HMDB0032586)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	76 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4822 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.91 g/L	ALOGPS
logP	2.08	ALOGPS
logP	1.66	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	15.62	ChemAxon
pKa (Strongest Basic)	-2.5	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	49.66 m³·mol⁻¹	ChemAxon
Polarizability	18.5 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]+	140.079	31661259
DarkChem	[M-H]-	138.353	31661259
DeepCCS	[M+H]+	137.23	30932474
DeepCCS	[M-H]-	133.558	30932474
DeepCCS	[M-2H]-	171.123	30932474
DeepCCS	[M+Na]+	146.661	30932474
AllCCS	[M+H]+	135.4	32859911
AllCCS	[M+H-H2O]+	130.9	32859911
AllCCS	[M+NH4]+	139.5	32859911
AllCCS	[M+Na]+	140.7	32859911
AllCCS	[M-H]-	137.2	32859911
AllCCS	[M+Na-2H]-	138.3	32859911
AllCCS	[M+HCOO]-	139.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-(4-Methoxyphenyl)-2-propen-1-ol	COC1=CC=C(\C=C\CO)C=C1	2451.9	Standard polar	33892256
3-(4-Methoxyphenyl)-2-propen-1-ol	COC1=CC=C(\C=C\CO)C=C1	1489.8	Standard non polar	33892256
3-(4-Methoxyphenyl)-2-propen-1-ol	COC1=CC=C(\C=C\CO)C=C1	1579.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-(4-Methoxyphenyl)-2-propen-1-ol,1TMS,isomer #1	COC1=CC=C(/C=C/CO[Si](C)(C)C)C=C1	1698.2	Semi standard non polar	33892256
3-(4-Methoxyphenyl)-2-propen-1-ol,1TBDMS,isomer #1	COC1=CC=C(/C=C/CO[Si](C)(C)C(C)(C)C)C=C1	1940.4	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 - 3-(4-Methoxyphenyl)-2-propen-1-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-008a-1900000000-cf94f621e793212b3d2d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(4-Methoxyphenyl)-2-propen-1-ol GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9630000000-d6e51997744161741c8f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(4-Methoxyphenyl)-2-propen-1-ol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(4-Methoxyphenyl)-2-propen-1-ol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methoxyphenyl)-2-propen-1-ol 10V, Positive-QTOF	splash10-00kb-0900000000-b254e737b0ea81d3ae6c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methoxyphenyl)-2-propen-1-ol 20V, Positive-QTOF	splash10-0002-1900000000-4ea1ce55f2742ffcea1e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methoxyphenyl)-2-propen-1-ol 40V, Positive-QTOF	splash10-100s-5900000000-81a8325c4ee7fa6a7573	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methoxyphenyl)-2-propen-1-ol 10V, Negative-QTOF	splash10-03di-0900000000-a88a819488e615a07a78	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methoxyphenyl)-2-propen-1-ol 20V, Negative-QTOF	splash10-03dj-0900000000-91d717282adc3237de78	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methoxyphenyl)-2-propen-1-ol 40V, Negative-QTOF	splash10-0691-3900000000-bf2e6bbbda48f363d797	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methoxyphenyl)-2-propen-1-ol 10V, Positive-QTOF	splash10-00xr-0900000000-434668d361e68e057301	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methoxyphenyl)-2-propen-1-ol 20V, Positive-QTOF	splash10-00yj-2900000000-02ea281558b74834e6c9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methoxyphenyl)-2-propen-1-ol 40V, Positive-QTOF	splash10-02dl-8900000000-8b42ebbb43185bf8d516	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methoxyphenyl)-2-propen-1-ol 10V, Negative-QTOF	splash10-01ot-0900000000-5cabc72ed586e3285650	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methoxyphenyl)-2-propen-1-ol 20V, Negative-QTOF	splash10-03xu-2900000000-6497851215971771cc33	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methoxyphenyl)-2-propen-1-ol 40V, Negative-QTOF	splash10-014i-0900000000-123b1d71f0ed667e65af	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB010523

KNApSAcK ID

Not Available

Chemspider ID

4473596

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5314180

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1462601

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 3-(4-Methoxyphenyl)-2-propen-1-ol (HMDB0032586)

MOL for HMDB0032586 (3-(4-Methoxyphenyl)-2-propen-1-ol)

3D MOL for HMDB0032586 (3-(4-Methoxyphenyl)-2-propen-1-ol)

3D SDF for HMDB0032586 (3-(4-Methoxyphenyl)-2-propen-1-ol)

3D-SDF for HMDB0032586 (3-(4-Methoxyphenyl)-2-propen-1-ol)

PDB for HMDB0032586 (3-(4-Methoxyphenyl)-2-propen-1-ol)

3D PDB for HMDB0032586 (3-(4-Methoxyphenyl)-2-propen-1-ol)

SMILES for HMDB0032586 (3-(4-Methoxyphenyl)-2-propen-1-ol)

INCHI for HMDB0032586 (3-(4-Methoxyphenyl)-2-propen-1-ol)

Structure for HMDB0032586 (3-(4-Methoxyphenyl)-2-propen-1-ol)

3D Structure for HMDB0032586 (3-(4-Methoxyphenyl)-2-propen-1-ol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra