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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:32:43 UTC

Update Date

2023-02-21 17:28:29 UTC

HMDB ID

HMDB0040932

Secondary Accession Numbers

HMDB40932

Metabolite Identification

Common Name

4-Chloro-3,5-dimethoxybenzaldehyde

Description

4-Chloro-3,5-dimethoxybenzaldehyde 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-dimethoxybenzaldehyde 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-dimethoxybenzaldehyde 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-dimethoxybenzaldehyde.

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

C₉H₉ClO₃

Average Molecular Weight

200.619

Monoisotopic Molecular Weight

200.024021861

IUPAC Name

4-chloro-3,5-dimethoxybenzaldehyde

Traditional Name

4-chloro-3,5-dimethoxybenzaldehyde

CAS Registry Number

56518-48-0

SMILES

COC1=CC(C=O)=CC(OC)=C1Cl

InChI Identifier

InChI=1S/C9H9ClO3/c1-12-7-3-6(5-11)4-8(13-2)9(7)10/h3-5H,1-2H3

InChI Key

GTEZQOCVTNORJP-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
Benzaldehyde
Phenol ether
Benzoyl
Alkyl aryl ether
Aryl-aldehyde
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Ether
Organochloride
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aldehyde
Organic oxide
Organohalogen 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: HMDB0040932)
Cytoplasm (HMDB: HMDB0040932)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040932)

Source

Exogenous

Exogenous (HMDB: HMDB0040932)

Food

Food (HMDB: HMDB0040932)

Plant (HMDB: HMDB0040932)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040932)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	165 - 167 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	308.1 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	0.23 g/L	ALOGPS
logP	2.3	ALOGPS
logP	1.97	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	50.37 m³·mol⁻¹	ChemAxon
Polarizability	18.93 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]+	139.719	30932474
DeepCCS	[M-H]-	136.986	30932474
DeepCCS	[M-2H]-	173.12	30932474
DeepCCS	[M+Na]+	148.658	30932474
AllCCS	[M+H]+	140.6	32859911
AllCCS	[M+H-H2O]+	136.5	32859911
AllCCS	[M+NH4]+	144.5	32859911
AllCCS	[M+Na]+	145.6	32859911
AllCCS	[M-H]-	137.3	32859911
AllCCS	[M+Na-2H]-	138.2	32859911
AllCCS	[M+HCOO]-	139.2	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.	5.23 minutes	32390414
Predicted by Siyang on May 30, 2022	15.2804 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.81 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1843.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	530.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	185.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	345.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	151.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	553.7 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	754.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	232.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1231.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	434.2 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	1443.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	428.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	449.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	616.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	554.3 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	128.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Chloro-3,5-dimethoxybenzaldehyde	COC1=CC(C=O)=CC(OC)=C1Cl	2458.6	Standard polar	33892256
4-Chloro-3,5-dimethoxybenzaldehyde	COC1=CC(C=O)=CC(OC)=C1Cl	1562.5	Standard non polar	33892256
4-Chloro-3,5-dimethoxybenzaldehyde	COC1=CC(C=O)=CC(OC)=C1Cl	1641.3	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-dimethoxybenzaldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uk9-2940000000-2aa2e882636698e93c58	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Chloro-3,5-dimethoxybenzaldehyde 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-dimethoxybenzaldehyde 10V, Positive-QTOF	splash10-0udi-0190000000-612ce76d08898eedc1a4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzaldehyde 20V, Positive-QTOF	splash10-0udi-0290000000-feb2034dfd2e24f50140	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzaldehyde 40V, Positive-QTOF	splash10-05wf-3900000000-202c71b8045c43fb16d4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzaldehyde 10V, Negative-QTOF	splash10-0002-0900000000-25c26560ec745a4e237f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzaldehyde 20V, Negative-QTOF	splash10-0002-0900000000-4f9c9442772a36a100c9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzaldehyde 40V, Negative-QTOF	splash10-0pis-9400000000-dd5425ae26955781f894	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzaldehyde 10V, Negative-QTOF	splash10-0002-0900000000-1f67dc27e639003cdbc6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzaldehyde 20V, Negative-QTOF	splash10-0002-0900000000-0a81244448abf4ec30f1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzaldehyde 40V, Negative-QTOF	splash10-00lr-9300000000-3e88f3921224ea5c466c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzaldehyde 10V, Positive-QTOF	splash10-0udi-0190000000-49d303b6a5bc7fb03020	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzaldehyde 20V, Positive-QTOF	splash10-0udi-0980000000-0cd3092bee541e93b2da	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Chloro-3,5-dimethoxybenzaldehyde 40V, Positive-QTOF	splash10-07f4-9400000000-904dddf9beb86393a8d6	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+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

FDB020773

KNApSAcK ID

C00054790

Chemspider ID

13460886

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12398450

PDB ID

Not Available

ChEBI ID

169519

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1887851

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-dimethoxybenzaldehyde (HMDB0040932)

MOL for HMDB0040932 (4-Chloro-3,5-dimethoxybenzaldehyde)

3D MOL for HMDB0040932 (4-Chloro-3,5-dimethoxybenzaldehyde)

3D SDF for HMDB0040932 (4-Chloro-3,5-dimethoxybenzaldehyde)

3D-SDF for HMDB0040932 (4-Chloro-3,5-dimethoxybenzaldehyde)

PDB for HMDB0040932 (4-Chloro-3,5-dimethoxybenzaldehyde)

3D PDB for HMDB0040932 (4-Chloro-3,5-dimethoxybenzaldehyde)

SMILES for HMDB0040932 (4-Chloro-3,5-dimethoxybenzaldehyde)

INCHI for HMDB0040932 (4-Chloro-3,5-dimethoxybenzaldehyde)

Structure for HMDB0040932 (4-Chloro-3,5-dimethoxybenzaldehyde)

3D Structure for HMDB0040932 (4-Chloro-3,5-dimethoxybenzaldehyde)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra