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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:32:46 UTC

Update Date

2023-02-21 17:28:30 UTC

HMDB ID

HMDB0040933

Secondary Accession Numbers

HMDB40933

Metabolite Identification

Common Name

4-Chloro-3,5-dimethoxybenzyl alcohol

Description

4-Chloro-3,5-dimethoxybenzyl alcohol belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups. 4-Chloro-3,5-dimethoxybenzyl alcohol has been detected, but not quantified in, a few different foods, such as common mushrooms (Agaricus bisporus), mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make 4-chloro-3,5-dimethoxybenzyl alcohol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Chloro-3,5-dimethoxybenzyl alcohol.

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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   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 Cl   UNK     0       1.334  -2.310   0.000  0.00  0.00          Cl+0
HETATM   11  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   13                                                            
CONECT    3    6    7                                                       
CONECT    4    6    8                                                       
CONECT    5    6   11                                                       
CONECT    6    3    4    5                                                  
CONECT    7    3    9   12                                                  
CONECT    8    4    9   13                                                  
CONECT    9    7    8   10                                                  
CONECT   10    9                                                            
CONECT   11    5                                                            
CONECT   12    1    7                                                       
CONECT   13    2    8                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₉H₁₁ClO₃

Average Molecular Weight

202.635

Monoisotopic Molecular Weight

202.039671925

IUPAC Name

(4-chloro-3,5-dimethoxyphenyl)methanol

Traditional Name

(4-chloro-3,5-dimethoxyphenyl)methanol

CAS Registry Number

152570-76-8

SMILES

COC1=CC(CO)=CC(OC)=C1Cl

InChI Identifier

InChI=1S/C9H11ClO3/c1-12-7-3-6(5-11)4-8(13-2)9(7)10/h3-4,11H,5H2,1-2H3

InChI Key

NEORIYMPRMFPGM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Methoxybenzenes

Direct Parent

Dimethoxybenzenes

Alternative Parents

Substituents

M-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Anisole
Phenol ether
Benzyl alcohol
Alkyl aryl ether
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Ether
Alcohol
Organohalogen compound
Organochloride
Organooxygen compound
Primary alcohol
Aromatic alcohol
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040933)
Cytoplasm (HMDB: HMDB0040933)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040933)

Source

Exogenous

Food

Food (HMDB: HMDB0040933)

Plant (HMDB: HMDB0040933)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040933)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	83 - 85 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3392 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	1.25 g/L	ALOGPS
logP	1.94	ALOGPS
logP	1.49	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	14.84	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	50.61 m³·mol⁻¹	ChemAxon
Polarizability	19.87 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
DeepCCS	[M+H]+	145.25	30932474
DeepCCS	[M-H]-	142.516	30932474
DeepCCS	[M-2H]-	178.894	30932474
DeepCCS	[M+Na]+	154.431	30932474
AllCCS	[M+H]+	141.7	32859911
AllCCS	[M+H-H2O]+	137.6	32859911
AllCCS	[M+NH4]+	145.6	32859911
AllCCS	[M+Na]+	146.7	32859911
AllCCS	[M-H]-	139.7	32859911
AllCCS	[M+Na-2H]-	140.7	32859911
AllCCS	[M+HCOO]-	141.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Chloro-3,5-dimethoxybenzyl alcohol	COC1=CC(CO)=CC(OC)=C1Cl	2765.6	Standard polar	33892256
4-Chloro-3,5-dimethoxybenzyl alcohol	COC1=CC(CO)=CC(OC)=C1Cl	1594.9	Standard non polar	33892256
4-Chloro-3,5-dimethoxybenzyl alcohol	COC1=CC(CO)=CC(OC)=C1Cl	1785.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Chloro-3,5-dimethoxybenzyl alcohol,1TMS,isomer #1	COC1=CC(CO[Si](C)(C)C)=CC(OC)=C1Cl	1735.9	Semi standard non polar	33892256
4-Chloro-3,5-dimethoxybenzyl alcohol,1TBDMS,isomer #1	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC(OC)=C1Cl	1965.4	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 - 4-Chloro-3,5-dimethoxybenzyl alcohol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-2910000000-0c1b6b28fb9da5f67820	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Chloro-3,5-dimethoxybenzyl alcohol GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-9360000000-e7ff7ded8185f413de40	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Chloro-3,5-dimethoxybenzyl alcohol 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 - 4-Chloro-3,5-dimethoxybenzyl alcohol 10V, Positive-QTOF	splash10-0udr-0980000000-705285b32e7e4f24671b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzyl alcohol 20V, Positive-QTOF	splash10-000i-0920000000-4106bc201cf1b70c5a46	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzyl alcohol 40V, Positive-QTOF	splash10-0a4r-4900000000-e8157b38378db9e395e0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzyl alcohol 10V, Negative-QTOF	splash10-0udi-0190000000-5da74bed4a9cf0eca11e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzyl alcohol 20V, Negative-QTOF	splash10-0uk9-0960000000-327738e06c153f9186f0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzyl alcohol 40V, Negative-QTOF	splash10-0a59-9800000000-1f5eef7d517f4b3f32a3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzyl alcohol 10V, Negative-QTOF	splash10-0udi-0090000000-6a71d942e1747e4bde30	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzyl alcohol 20V, Negative-QTOF	splash10-0v59-2930000000-4b1a22539ecd1bd51e82	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzyl alcohol 40V, Negative-QTOF	splash10-053r-9100000000-2db3dec1cc40b68f6144	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzyl alcohol 10V, Positive-QTOF	splash10-0udi-0190000000-15fa4f71e0aaf1278fa7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzyl alcohol 20V, Positive-QTOF	splash10-0f79-0920000000-32b24ed18c918d1ae8c1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzyl alcohol 40V, Positive-QTOF	splash10-0a6u-9400000000-c2783d20c4e2fd971fb4	2021-09-24	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

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

FDB020774

KNApSAcK ID

C00055064

Chemspider ID

30777525

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

84777014

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1887861

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 4-Chloro-3,5-dimethoxybenzyl alcohol (HMDB0040933)

MOL for HMDB0040933 (4-Chloro-3,5-dimethoxybenzyl alcohol)

3D MOL for HMDB0040933 (4-Chloro-3,5-dimethoxybenzyl alcohol)

3D SDF for HMDB0040933 (4-Chloro-3,5-dimethoxybenzyl alcohol)

3D-SDF for HMDB0040933 (4-Chloro-3,5-dimethoxybenzyl alcohol)

PDB for HMDB0040933 (4-Chloro-3,5-dimethoxybenzyl alcohol)

3D PDB for HMDB0040933 (4-Chloro-3,5-dimethoxybenzyl alcohol)

SMILES for HMDB0040933 (4-Chloro-3,5-dimethoxybenzyl alcohol)

INCHI for HMDB0040933 (4-Chloro-3,5-dimethoxybenzyl alcohol)

Structure for HMDB0040933 (4-Chloro-3,5-dimethoxybenzyl alcohol)

3D Structure for HMDB0040933 (4-Chloro-3,5-dimethoxybenzyl alcohol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra