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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:13:26 UTC
Update Date2019-07-23 06:18:12 UTC
HMDB IDHMDB0035268
Secondary Accession Numbers
  • HMDB35268
Metabolite Identification
Common Name4-Isopropylbenzoic acid
Description4-Isopropylbenzoic acid, also known as cumic acid or 4-(1-methylethyl)benzoate, belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Based on a literature review a significant number of articles have been published on 4-Isopropylbenzoic acid.
Structure
Data?1563862692
Synonyms
ValueSource
4-(1-Methylethyl)benzoic acidChEBI
4-Propan-2-ylbenzoic acidChEBI
Cumic acidChEBI
Cuminic acidChEBI
p-Isopropylbenzoic acidChEBI
4-(1-Methylethyl)benzoateGenerator
4-Propan-2-ylbenzoateGenerator
CumateGenerator
CuminateGenerator
p-IsopropylbenzoateGenerator
4-IsopropylbenzoateGenerator
4-(1-Methylethyl)-benzoic acidHMDB
4-(1-Methylethyl)benzoic acid, 9ciHMDB
4-(Propan-2-yl)benzoic acidHMDB
Benzoic acid, P-isopropyl- (8ci)HMDB
P-CumateHMDB, Generator, MeSH
P-Cumic acidHMDB
P-Isopropyl-benzoic acidHMDB
4-Isopropylbenzoic acidChEBI
Chemical FormulaC10H12O2
Average Molecular Weight164.204
Monoisotopic Molecular Weight164.083729626
IUPAC Name4-(propan-2-yl)benzoic acid
Traditional Name4-isopropylbenzoic acid
CAS Registry Number536-66-3
SMILES
CC(C)C1=CC=C(C=C1)C(O)=O
InChI Identifier
InChI=1S/C10H12O2/c1-7(2)8-3-5-9(6-4-8)10(11)12/h3-7H,1-2H3,(H,11,12)
InChI KeyCKMXAIVXVKGGFM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • P-cymene
  • Aromatic monoterpenoid
  • Monocyclic monoterpenoid
  • Benzoic acid or derivatives
  • Benzoic acid
  • Cumene
  • Phenylpropane
  • Benzoyl
  • Monocyclic benzene moiety
  • Benzenoid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point117 - 118 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.15 mg/mL at 25 °CNot Available
LogP3.40Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
logP10(2.86) g/LALOGPS
logP10(2.88) g/LChemAxon
logS10(-2.8) g/LALOGPS
pKa (Strongest Acidic)4.23ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.5 m³·mol⁻¹ChemAxon
Polarizability18.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.15231661259
DarkChem[M-H]-134.52231661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Isopropylbenzoic acid,1TMS,#1CC(C)C1=CC=C(C(=O)O[Si](C)(C)C)C=C11536.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
4-Isopropylbenzoic acid,1TBDMS,#1CC(C)C1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C11769.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Isopropylbenzoic acid GC-EI-TOF (Non-derivatized)splash10-0fmm-1920000000-9ba5c2ba437afcaccb5c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Isopropylbenzoic acid GC-EI-TOF (Non-derivatized)splash10-0fmm-1920000000-9ba5c2ba437afcaccb5c2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Isopropylbenzoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-2900000000-cea1ff1e3c33d541d0a32017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Isopropylbenzoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9630000000-a3b0b91819234895d2fd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Isopropylbenzoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Isopropylbenzoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Isopropylbenzoic acid LC-ESI-QQ , negative-QTOFsplash10-03di-0900000000-7c3ba8dd3d96d50684142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Isopropylbenzoic acid LC-ESI-QQ , negative-QTOFsplash10-014i-0900000000-f75e646d4bf6e224878b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Isopropylbenzoic acid LC-ESI-QQ , negative-QTOFsplash10-014i-0900000000-ed664f663776643244452017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Isopropylbenzoic acid LC-ESI-QQ , negative-QTOFsplash10-001i-9000000000-a302fe096dbf58098b852017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isopropylbenzoic acid 10V, Positive-QTOFsplash10-014j-0900000000-e762053fdf0cef76811c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isopropylbenzoic acid 20V, Positive-QTOFsplash10-014j-0900000000-515bab2d5d7f088937972016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isopropylbenzoic acid 40V, Positive-QTOFsplash10-0gbd-4900000000-6159ae29376d553623ee2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isopropylbenzoic acid 10V, Negative-QTOFsplash10-03di-0900000000-072170d646d6f1372fb22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isopropylbenzoic acid 20V, Negative-QTOFsplash10-02t9-0900000000-b93b896ef35b4c1ede9e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isopropylbenzoic acid 40V, Negative-QTOFsplash10-014i-3900000000-c6ecb319a8a4661f78c32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isopropylbenzoic acid 10V, Positive-QTOFsplash10-014i-0900000000-798f83fde0f53d0b19d02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isopropylbenzoic acid 20V, Positive-QTOFsplash10-066r-2900000000-cc737492d35c24e923a72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isopropylbenzoic acid 40V, Positive-QTOFsplash10-00mo-9500000000-b97df83159f595b8acd02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isopropylbenzoic acid 10V, Negative-QTOFsplash10-03di-0900000000-8db47caa9667c101bd0f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isopropylbenzoic acid 20V, Negative-QTOFsplash10-02t9-0900000000-b58ee206173547f641f32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isopropylbenzoic acid 40V, Negative-QTOFsplash10-0ufr-9600000000-2e53de283919c1fb59312021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013929
KNApSAcK IDC00036581
Chemspider ID10363
KEGG Compound IDC06578
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10820
PDB IDNot Available
ChEBI ID28122
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1204141
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.