Showing Compound Card for 3,4-Dimethylbenzoic acid (CDB005687)

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Record Information
Version1.0
Created at2020-04-27 16:45:39 UTC
Updated at2021-01-04 18:49:08 UTC
CannabisDB IDCDB005687
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name3,4-Dimethylbenzoic acid
Description3,4-Dimethylbenzoic acid is a dimethylated derivative of benzoic acid in which two methyl substituents positioning at C-3 and C-4 of the benzene ring. 3,4-Dimethylbenzoic acid belongs to the class of organic compounds known as benzoic acids. These are organic compounds containing a benzene ring which bears at least one carboxyl group. 3,4-Dimethylbenzoic acid exists as a white to beige crystalline powder that is weakly water soluble. It has been detected, but not quantified in a small number of plants (Eryngium foetidum), herbs and spices. 3,4-Dimethylbenzoic acid is also found in human feces and appears to be a microbial byproduct arising from the digestion of polyphenols. It has recently been found that 3,4-Dimethylbenzoic acid acts as a strong inhibitor of hilA expression and prevents the invasion of cultured host cells by Salmonella (PMID: 28754707 ). The hilA gene encodes the master regulator of invasion genes in Salmonella. On the other hand, 3,4-dimethylbenzoic acid has also been shown to preferentially induce expression of flagellin, a bacterial protein associated with the motility of enterohemorrhagic Escherichia coli (EHEC) which may lead to increased epithelial injuries (PMID: 30890187 ). EHEC is a subgroup of Shiga toxin (Stx)-producing E. coli that is a leading cause of diarrhea and hemolytic-uremic syndrome (HUS) in humans. 3,4-Dimethylbenzoic acid is a constituent of marijuana (cannabis) smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Carboxy-3,4-dimethylbenzeneChEBI
3,4-DimethylbenzoateGenerator
Chemical FormulaC9H10O2
Average Molecular Weight150.17
Monoisotopic Molecular Weight150.0681
IUPAC Name3,4-dimethylbenzoic acid
Traditional Name3,4-dimethylbenzoic acid
CAS Registry Number619-04-5
SMILES
CC1=C(C)C=C(C=C1)C(O)=O
InChI Identifier
InChI=1S/C9H10O2/c1-6-3-4-8(9(10)11)5-7(6)2/h3-5H,1-2H3,(H,10,11)
InChI KeyOPVAJFQBSDUNQA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acids
Alternative Parents
Substituents
  • Benzoic acid
  • O-xylene
  • Xylene
  • Benzoyl
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point165 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.13 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.28ALOGPS
logP2.66ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)4.27ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.4 m³·mol⁻¹ChemAxon
Polarizability16.15 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3,4-Dimethylbenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zgi-2900000000-80eb1dd309058448739cSpectrum
Predicted GC-MS3,4-Dimethylbenzoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05gi-9540000000-dd6cb0d165c5e6ca06caSpectrum
Predicted GC-MS3,4-Dimethylbenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,4-Dimethylbenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-0900000000-fadbc0c62061c2e094772020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0002-0900000000-b038961ede38d1c8d4e12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0002-0900000000-198e824f91c327b081fd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-052b-0900000000-963285484eb6bef9ec592020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0a4j-0900000000-e76cad5bdc148adcaad62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0a4i-0900000000-cf6a9c58c766ce99168c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0a4i-0900000000-7a04f8ceeb71dfe883ea2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-0a4i-0900000000-bd45484b2007c28fadc22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-004i-9000000000-8c963d0a5e5187bda7af2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0udi-0900000000-aa68ff00ecb8cf48e3702020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-0900000000-2fb9bf768b13527547d02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-0900000000-98c8a3073d2bb0c950d72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0zfr-0900000000-84ec3fb159d902048a442020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0pb9-0900000000-5b1fa52d590c8c846fcc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a4i-0900000000-381998616392043e4a172020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a4i-0900000000-5981a5161f24a0f4b93f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a4i-0900000000-95bf2476e7cc7f8b62542020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0a4i-1900000000-6ea7be4a18f689cb78362020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0a4i-3900000000-57fb9272bc971dfa86bf2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0900000000-732d9a4dd1b2cd8017452016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-0900000000-fbbe91357c205eb166c52016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9800000000-e3ac5a01ad52d17c8ca72016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-5ef22341afc38c8fa1102016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-0900000000-45d060e81db537ec43f32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4900000000-1b5a814b00cb65f17e1b2016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0002237
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008869
KNApSAcK IDC00058147
Chemspider ID11576
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6565
PubChem Compound12073
PDB IDNot Available
ChEBI ID64818
References
General References
  1. Peixoto RJM, Alves ES, Wang M, Ferreira RBR, Granato A, Han J, Gill H, Jacobson K, Lobo LA, Domingues RMCP, Borchers CH, Davies JE, Finlay BB, Antunes LCM: Repression of Salmonella Host Cell Invasion by Aromatic Small Molecules from the Human Fecal Metabolome. Appl Environ Microbiol. 2017 Sep 15;83(19). pii: AEM.01148-17. doi: 10.1128/AEM.01148-17. Print 2017 Oct 1. [PubMed:28754707 ]
  2. Tovaglieri A, Sontheimer-Phelps A, Geirnaert A, Prantil-Baun R, Camacho DM, Chou DB, Jalili-Firoozinezhad S, de Wouters T, Kasendra M, Super M, Cartwright MJ, Richmond CA, Breault DT, Lacroix C, Ingber DE: Species-specific enhancement of enterohemorrhagic E. coli pathogenesis mediated by microbiome metabolites. Microbiome. 2019 Mar 20;7(1):43. doi: 10.1186/s40168-019-0650-5. [PubMed:30890187 ]