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Showing Compound 1-Isopropyl-4-methylbenzene (FDB017358)

Record Information
Version1.0
Creation date2010-04-08 22:13:02 UTC
Update date2020-09-17 15:30:00 UTC
Primary IDFDB017358
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1-Isopropyl-4-methylbenzene
Descriptionp-Cymene, also known as p-cymol or isopropyltoluene, belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.Its structure consists of a benzene ring para-substituted with a methyl group and an isopropyl group. Thus, p-cymene is considered to be an isoprenoid lipid molecule. p-Cymene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.It has a role as a plant metabolite, a volatile oil component. p-Cymene
CAS Number99-87-6
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
1-Isopropyl-4-methylbenzeneChEBI
1-Methyl-4-(1-methylethyl)benzeneChEBI
1-Methyl-4-(propan-2-yl)benzeneChEBI
1-Methyl-4-isopropylbenzeneChEBI
4-CymeneChEBI
4-Isopropyl-1-methylbenzeneChEBI
4-IsopropyltolueneChEBI
4-Methyl-1-isopropylbenzeneChEBI
CymeneChEBI
IsopropyltolueneChEBI
p-CimeneChEBI
p-CymolChEBI
p-IsopropyltolueneChEBI
p-MethylcumeneChEBI
p-MethylisopropylbenzeneChEBI
Para-cymeneChEBI
1-Isopropyl-4-methyl-benzeneHMDB
1-Methyl-4-(1-methylethyl)-benzeneHMDB
2-p-TolylpropaneHMDB
4-Isopropylbenzyl radicalHMDB
4-Methyl-1-(propan-2-yl)benzeneHMDB
CamphogenHMDB
CymolHMDB
DolcymeneHMDB
P- IsopropylmethylbenzeneHMDB
P-Mentha-1,3,5-trieneHMDB
P-Methyl cumeneHMDB
P-Methyl-cumeneHMDB
ParacymeneHMDB
ParacymolHMDB
4-MethylisopropylbenzenePhytoBank
1-(1-methylethyl)-4-methylbenzenebiospider
1-isopropyl-4-methyl-Benzenebiospider
1-Methyl-4-(1-methylethyl)benzene, 9CIdb_source
4-Cymolbiospider
4-Isopropyltoluolbiospider
4-methyl isopropylbenzenebiospider
4-methyl-1-(propan-2-yl)benzenebiospider
Benzene, 1-isopropyl-4-methyl-biospider
Benzene, 1-methyl-4-(1-methylethyl)-biospider
benzene, 1-methyl-4-methylethyl-biospider
Camphene (obsol.)db_source
Camphogene (obsol.)db_source
Cumene, p-methyl-biospider
Cymene, p-biospider
FEMA 2356db_source
Methyl-4-(1-methylethyl)benzenebiospider
P- isopropylmethylbenzenebiospider
P-cimenebiospider
p-Cymenedb_source
P-isopropylmethylbenzenebiospider
p-Mentha-1,3,5-trienedb_source
P-methyl cumenebiospider
P-methyl-cumenebiospider
P-methylcumenebiospider
P-methylisopropylbenzenebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP4.17ALOGPS
logP3.73ChemAxon
logS-3.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.29 m³·mol⁻¹ChemAxon
Polarizability17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H14
IUPAC name1-methyl-4-(propan-2-yl)benzene
InChI IdentifierInChI=1S/C10H14/c1-8(2)10-6-4-9(3)5-7-10/h4-8H,1-3H3
InChI KeyHFPZCAJZSCWRBC-UHFFFAOYSA-N
Isomeric SMILESCC(C)C1=CC=C(C)C=C1
Average Molecular Weight134.222
Monoisotopic Molecular Weight134.109550451
Classification
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
  • Monocyclic monoterpenoid
  • Aromatic monoterpenoid
  • P-cymene
  • Phenylpropane
  • Cumene
  • Toluene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aromatic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateGas
Physical DescriptionNot Available
Mass CompositionC 89.49%; H 10.51%DFC
Melting PointMp -67.94°DFC
Boiling PointBp 177.1°DFC
Experimental Water Solubility0.0234 mg/mL at 25 oCBANERJEE,S et al. (1980)
Experimental logP4.10HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-014i-4900000000-c8d4189d8e9f124c75ad2014-09-20View Spectrum
GC-MS1-Isopropyl-4-methylbenzene, non-derivatized, GC-MS Spectrumsplash10-014i-4900000000-f403355796ccc97b5011Spectrum
GC-MS1-Isopropyl-4-methylbenzene, non-derivatized, GC-MS Spectrumsplash10-014i-3900000000-18fab12c9b06d75f28d4Spectrum
GC-MS1-Isopropyl-4-methylbenzene, non-derivatized, GC-MS Spectrumsplash10-001i-0900000000-146f5d56238ffde0a8d0Spectrum
GC-MS1-Isopropyl-4-methylbenzene, non-derivatized, GC-MS Spectrumsplash10-007x-4900000000-14f27e732fc9b57e0b12Spectrum
GC-MS1-Isopropyl-4-methylbenzene, non-derivatized, GC-MS Spectrumsplash10-014i-4900000000-f403355796ccc97b5011Spectrum
GC-MS1-Isopropyl-4-methylbenzene, non-derivatized, GC-MS Spectrumsplash10-014i-3900000000-18fab12c9b06d75f28d4Spectrum
GC-MS1-Isopropyl-4-methylbenzene, non-derivatized, GC-MS Spectrumsplash10-001i-0900000000-146f5d56238ffde0a8d0Spectrum
GC-MS1-Isopropyl-4-methylbenzene, non-derivatized, GC-MS Spectrumsplash10-007x-4900000000-14f27e732fc9b57e0b12Spectrum
Predicted GC-MS1-Isopropyl-4-methylbenzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014l-8900000000-176f8c1c70e1e67b3d82Spectrum
Predicted GC-MS1-Isopropyl-4-methylbenzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-94c1bdcd85003d97aefc2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2900000000-5ed611e91a5f86fc70192016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9700000000-f812cd4b0a2fcb99f91a2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-3043af674a7adea6117a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-589b3edc66f090e075e52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lu-4900000000-9166f98044ef814ac56b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-f5fa2e4eafb73a2ce5ef2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-f5fa2e4eafb73a2ce5ef2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9200000000-0d66e02ef78a9a9bac9a2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-9800000000-f6dc3a9bc8c029e844ff2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9100000000-31308f391d491363333e2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9000000000-0f55cd38142065afafc32021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, CDCl3, experimental)Spectrum
ChemSpider ID7183
ChEMBL IDCHEMBL442915
KEGG Compound IDC06575
Pubchem Compound ID7463
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05805
CRC / DFC (Dictionary of Food Compounds) IDKXH73-P:KXH73-P
EAFUS ID812
Dr. Duke IDP-CYMOL|P-CYMENE|CYMOL
BIGG IDNot Available
KNApSAcK IDC00003040
HET IDMML
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID99-87-6
GoodScent IDrw1032711
SuperScent IDNot Available
Wikipedia IDP-cymene
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Analgesic35480 An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.DUKE
Anti acetylcholinesterase38462 An agent that inhibits acetylcholinesterase, increasing acetylcholine levels. It enhances cholinergic transmission, used therapeutically to treat Alzheimer's disease, myasthenia gravis, and glaucoma, improving cognitive function, muscle strength, and reducing intraocular pressure.DUKE
Anti-bacillary33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating bacterial infections. Therapeutically, it is used to combat bacterial diseases, with key medical applications including the treatment of tuberculosis, pneumonia, and other infectious diseases.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti-flu22587 An agent that prevents or treats influenza virus infections, reducing symptoms and complications. Its biological role involves blocking viral replication, and its therapeutic applications include prophylaxis and treatment of flu outbreaks. Key medical uses include reducing the risk of flu-related hospitalizations and mortality, especially in high-risk populations such as the elderly and young children.DUKE
Anti-rheumatalgic52217 An agent that alleviates rheumatic pain and inflammation, commonly used in managing arthritis, fibromyalgia, and other musculoskeletal disorders, reducing joint pain and improving mobility.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
Name48318 flavorDUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
Herbicide24527 A chemical agent that kills or inhibits plant growth, used in agriculture to control weeds and pests. It has no direct biological role or therapeutic applications in human medicine, but its development has led to the creation of related compounds with potential medical uses, such as anticancer agents.DUKE
Insectifuge24852 A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission.DUKE
IrritantAn agent that causes slight inflammation or discomfort, stimulating a biological response. Therapeutically, it can be used to increase blood flow or stimulate healing. Key medical uses include treating wounds, skin conditions, and respiratory issues, such as congestion, by inducing a mild inflammatory response to promote recovery.DUKE
Laxative50503 An agent that stimulates bowel movements, relieving constipation by softening stool or increasing intestinal motility. Therapeutically, laxatives are used to treat constipation, prepare the bowel for medical procedures, and manage certain medical conditions, such as irritable bowel syndrome.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Sedative35717 An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.DUKE
TrichomonicideAn agent that kills Trichomonas organisms, used to treat Trichomonas vaginalis infections, commonly causing vaginitis, and other related genital tract infections.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
solvent
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
gasoline
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
citrus
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
terpene
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spice
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.