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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:09:47 UTC

Update Date

2023-02-21 17:17:51 UTC

HMDB ID

HMDB0012915

Secondary Accession Numbers

HMDB12915

Metabolite Identification

Common Name

Coniferyl alcohol

Description

Coniferyl alcohol (CAS: 458-35-5), also known as coniferol, 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. Coniferyl alcohol is an organic compound. When copolymerized with related aromatic compounds, coniferyl alcohol forms lignin or lignans. Coniferyl alcohol is an intermediate in the biosynthesis of eugenol, stilbenoids, and coumarin. Outside of the human body, coniferyl alcohol has been detected, but not quantified in, several different foods, such as common sages, chestnuts, cereals and cereal products, gingers, and cashew nuts. This could make coniferyl alcohol a potential biomarker for the consumption of these foods. Gum benzoin contains a significant amount of coniferyl alcohol and its esters. Coniferyl alcohol is an organic compound. This colourless crystalline solid is a phytochemical, one of the monolignols. It is synthesized via the phenylpropanoid biochemical pathway.

Structure

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

HEADER    PROTEIN                                 21-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUL-20         0                                  
HETATM    1  C   UNK     0    8668.0348668.205   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.3688667.436   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8670.7028668.205   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8672.0368667.436   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8662.7078668.205   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8661.3718667.436   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8662.7078665.129   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8666.7068667.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.3738668.207   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8664.0398667.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.0398665.897   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.3728665.127   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.7068665.897   0.000  0.00  0.00           C+0
CONECT    1    2    8                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    6   10                                                       
CONECT    6    5                                                            
CONECT    7   11                                                            
CONECT    8    9   13    1                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11    5                                                  
CONECT   11   10   12    7                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-Coniferol	ChEBI
4-(3-Hydroxy-1-propenyl)-2-methoxyphenol	ChEBI
4-[(1E)-3-Hydroxy-1-propenyl]-2-methoxyphenol	ChEBI
trans-Coniferol	ChEBI
trans-Coniferyl alcohol	ChEBI
Coniferol	Kegg
(e) 3-(4-Hydroxy-3-methoxyphenyl)-2-propen-1-ol	HMDB
3-(4-Hydroxy-3-methoxyphenyl)-2-propen-1-ol	HMDB
3-(4-Hydroxy-3-methoxyphenyl)allyl alcohol	HMDB
4-((1E)-3-Hydroxy-1-propenyl)-2-methoxyphenol	HMDB
4-(3-Hydroxy-1-propenyl)-2-methoxy-phenol	HMDB
4-Hydroxy-3-methoxycinnamic alcohol	HMDB
4-Hydroxy-3-methoxycinnamyl alcohol	HMDB
4-[(1E)-3-Hydroxyprop-1-en-1-yl]-2-methoxyphenol	HMDB
Coniferyl-alcohol	HMDB
Coniferylic alcohol	HMDB
e-Coniferyl alcohol	HMDB
gamma-Hydroxyisoeugenol	HMDB
p-Hydroxy-m-methoxycinnamyl alcohol	HMDB
(e)-4-(3-Hydroxyprop-1-en-1-yl)-2-methoxyphenol	HMDB
(e)-Coniferyl alcohol	HMDB
3-(4-Hydroxy-3-methoxyphenyl)-2-propenol	HMDB
3-(p-Hydroxy-m-methoxyphenyl)-2-propen-1-ol	HMDB
4-(3-Hydroxy-1-propen-1-yl)-2-methoxyphenol	HMDB
4-[(1E)-3-Hydroxy-1-propen-1-yl]-2-methoxyphenol	HMDB
4-[(e)-3-Hydroxy-1-propenyl]-2-methoxyphenol	HMDB
trans-3-(4-Hydroxy-3-methoxyphenyl)-2-propen-1-ol	HMDB
Γ-hydroxyisoeugenol	HMDB
Coniferyl alcohol	ChEBI

Chemical Formula

C₁₀H₁₂O₃

Average Molecular Weight

180.2005

Monoisotopic Molecular Weight

180.07864425

IUPAC Name

4-[(1E)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenol

Traditional Name

coniferyl alcohol

CAS Registry Number

32811-40-8

SMILES

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

InChI Identifier

InChI=1S/C10H12O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h2-5,7,11-12H,6H2,1H3/b3-2+

InChI Key

JMFRWRFFLBVWSI-NSCUHMNNSA-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

Cinnamyl alcohol
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:17745 )
phenylpropanoid (CHEBI:17745 )
monomethoxybenzene (CHEBI:17745 )
Coniferyl alcohol derivatives (C00590 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	74 °C	Not Available
Boiling Point	332.00 to 333.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	17210 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.920 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	138.177	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000309

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.78 g/L	ALOGPS
logP	1.51	ALOGPS
logP	1.35	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	9.98	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.64 m³·mol⁻¹	ChemAxon
Polarizability	19.28 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	143.315	31661259
DarkChem	[M-H]-	141.701	31661259
DeepCCS	[M+H]+	141.027	30932474
DeepCCS	[M-H]-	137.288	30932474
DeepCCS	[M-2H]-	174.769	30932474
DeepCCS	[M+Na]+	150.308	30932474
AllCCS	[M+H]+	139.5	32859911
AllCCS	[M+H-H2O]+	135.2	32859911
AllCCS	[M+NH4]+	143.4	32859911
AllCCS	[M+Na]+	144.6	32859911
AllCCS	[M-H]-	139.2	32859911
AllCCS	[M+Na-2H]-	140.1	32859911
AllCCS	[M+HCOO]-	141.2	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.	3.81 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7728 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.53 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1452.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	291.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	120.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	169.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	86.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	379.5 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	329.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	113.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	855.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	320.2 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	889.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	242.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	311.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	424.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	229.0 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	50.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Coniferyl alcohol	COC1=C(O)C=CC(\C=C\CO)=C1	2874.7	Standard polar	33892256
Coniferyl alcohol	COC1=C(O)C=CC(\C=C\CO)=C1	1676.4	Standard non polar	33892256
Coniferyl alcohol	COC1=C(O)C=CC(\C=C\CO)=C1	1738.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Coniferyl alcohol,1TMS,isomer #1	COC1=CC(/C=C/CO)=CC=C1O[Si](C)(C)C	1802.1	Semi standard non polar	33892256
Coniferyl alcohol,1TMS,isomer #2	COC1=CC(/C=C/CO[Si](C)(C)C)=CC=C1O	1881.0	Semi standard non polar	33892256
Coniferyl alcohol,2TMS,isomer #1	COC1=CC(/C=C/CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1930.4	Semi standard non polar	33892256
Coniferyl alcohol,1TBDMS,isomer #1	COC1=CC(/C=C/CO)=CC=C1O[Si](C)(C)C(C)(C)C	2065.5	Semi standard non polar	33892256
Coniferyl alcohol,1TBDMS,isomer #2	COC1=CC(/C=C/CO[Si](C)(C)C(C)(C)C)=CC=C1O	2110.9	Semi standard non polar	33892256
Coniferyl alcohol,2TBDMS,isomer #1	COC1=CC(/C=C/CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2418.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Coniferyl alcohol GC-MS (2 TMS)	splash10-0udl-2892000000-8e09702bbe43408dea53	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Coniferyl alcohol GC-EI-TOF (Non-derivatized)	splash10-0udl-1971000000-58a2f40e1a35d994d8ce	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Coniferyl alcohol GC-MS (Non-derivatized)	splash10-0udl-2892000000-8e09702bbe43408dea53	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Coniferyl alcohol GC-EI-TOF (Non-derivatized)	splash10-0udi-1971000000-886be2fff2ae0775e29a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coniferyl alcohol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w3a-0900000000-c3f5aeffcba96abe41da	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coniferyl alcohol GC-MS (2 TMS) - 70eV, Positive	splash10-0kp0-8194000000-8bc8f9ae4a3bf62fa091	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coniferyl alcohol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coniferyl alcohol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0f80-9700000000-1f147bafa37d424b58e0	2015-03-01	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 - Coniferyl alcohol 10V, Positive-QTOF	splash10-03e9-0900000000-f6bbbda70bec57d54aae	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coniferyl alcohol 20V, Positive-QTOF	splash10-03ei-1900000000-3d071a468ccb93b13a93	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coniferyl alcohol 40V, Positive-QTOF	splash10-059i-7900000000-90868b3f0a488e617d4d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coniferyl alcohol 10V, Negative-QTOF	splash10-004i-0900000000-c729b8f0720bcdcdde7d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coniferyl alcohol 20V, Negative-QTOF	splash10-01t9-0900000000-4dbcd2c4d0c5f7bf5419	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coniferyl alcohol 40V, Negative-QTOF	splash10-052o-3900000000-4d122ceec54b7f8cab5d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coniferyl alcohol 10V, Negative-QTOF	splash10-004i-0900000000-074bf952f4105e8f10d2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coniferyl alcohol 20V, Negative-QTOF	splash10-00di-0900000000-494e5e2f6e97fd314483	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coniferyl alcohol 40V, Negative-QTOF	splash10-003r-2900000000-4533325c29a82a96f32b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coniferyl alcohol 10V, Positive-QTOF	splash10-001r-0900000000-e7b51828e724301da666	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coniferyl alcohol 20V, Positive-QTOF	splash10-001i-0900000000-73c4d6f6f4b8b6f0cbb0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coniferyl alcohol 40V, Positive-QTOF	splash10-0a4i-6900000000-70c7e7ed6d9cf3dbdcbf	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Coniferyl_alcohol

METLIN ID

Not Available

PubChem Compound

1549095

PDB ID

N7I

ChEBI ID

17745

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1231201

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Melchers LS, Regensburg-Tuink AJ, Schilperoort RA, Hooykaas PJ: Specificity of signal molecules in the activation of Agrobacterium virulence gene expression. Mol Microbiol. 1989 Jul;3(7):969-77. [PubMed:2796734 ]
Panossian A, Kocharian A, Matinian K, Amroyan E, Gabrielian E, Mayr C, Wagner H: Pharmacological activity of phenylpropanoids of the mistletoe, Viscum album L., host: Pyrus caucasica Fed. Phytomedicine. 1998 Mar;5(1):11-7. doi: 10.1016/S0944-7113(98)80053-6. [PubMed:23195693 ]

Enzymes

Enzyme Details

1. Peroxiredoxin-6

General function:: Involved in antioxidant activity
Specific function:: Involved in redox regulation of the cell. Can reduce H(2)O(2) and short chain organic, fatty acid, and phospholipid hydroperoxides. May play a role in the regulation of phospholipid turnover as well as in protection against oxidative injury.
Gene Name:: PRDX6
Uniprot ID:: P30041
Molecular weight:: 25034.715

Reactions

Coniferyl alcohol → Guaiacyl lignin	details

Showing metabocard for Coniferyl alcohol (HMDB0012915)

MOL for HMDB0012915 (Coniferyl alcohol)

3D MOL for HMDB0012915 (Coniferyl alcohol)

3D SDF for HMDB0012915 (Coniferyl alcohol)

3D-SDF for HMDB0012915 (Coniferyl alcohol)

PDB for HMDB0012915 (Coniferyl alcohol)

3D PDB for HMDB0012915 (Coniferyl alcohol)

SMILES for HMDB0012915 (Coniferyl alcohol)

INCHI for HMDB0012915 (Coniferyl alcohol)

Structure for HMDB0012915 (Coniferyl alcohol)

3D Structure for HMDB0012915 (Coniferyl alcohol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

Reactions