CARVACROL (CHEM005027)

Record Information
Version1.0
Creation Date2016-05-19 01:57:24 UTC
Update Date2026-05-14 19:57:59 UTC
Accession NumberCHEM005027
Identification
Common NameCARVACROL
ClassSmall Molecule
Description
A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Insecticide
  • PFAS
  • Phytotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Hydroxy-2-methyl-5-isopropylbenzeneChEBI
1-Methyl-2-hydroxy-4-isopropylbenzeneChEBI
2-Hydroxy-p-cymeneChEBI
2-Methyl-5-(1-methylethyl)phenolChEBI
2-Methyl-5-isopropylphenolChEBI
2-p-CymenolChEBI
3-Isopropyl-6-methylphenolChEBI
5-Isopropyl-O-cresolChEBI
2-Hydroxy-4-isopropyl-1-methylbenzeneHMDB
2-HydroxycymeneHMDB
2-Methyl-5-(1-methylethyl)-phenolHMDB
3-Isopropyl-6-methyl-phenolHMDB
5-Isopropyl-2-methyl-phenolHMDB
6-Methyl-3-isopropylphenolHMDB
AntioxineHMDB
BENZENE,2-hydroxy,4-isopropyl,1-methyl carvacrolHMDB
CarvacrolHMDB
CymenolHMDB
CymophenolHMDB
FEMA 2245HMDB
Hydroxy-P-cymeneHMDB
Isopropyl-O-cresolHMDB
IsothymolHMDB
Isothymol (=2-isopropyl-4-methyl phenol)HMDB
KarvakrolHMDB
Methyl-5-(1-methylethyl)phenolHMDB
O-ThymolHMDB
OxycymolHMDB
P-Cymen-2-olHMDB
P-Cymene-2-olHMDB
P-Mentha-1,3,5-trien-2-olHMDB
5-Isopropyl-2-methylphenolChEBI
Chemical FormulaC10H14O
Average Molecular Mass150.221 g/mol
Monoisotopic Mass150.104 g/mol
CAS Registry Number499-75-2
IUPAC Name2-methyl-5-(propan-2-yl)phenol
Traditional Namecarvacrol
SMILESCC(C)C1=CC(O)=C(C)C=C1
InChI IdentifierInChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4-7,11H,1-3H3
InChI KeyRECUKUPTGUEGMW-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
  • Cumene
  • Phenylpropane
  • O-cresol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Toluene
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.47 g/LALOGPS
logP3.2ALOGPS
logP3.43ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)10.42ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.27 m³·mol⁻¹ChemAxon
Polarizability17.88 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0035770
FooDB IDFDB014512
Phenol Explorer ID672
KNApSAcK IDC00000156
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCarvacrol
Chemspider ID21105867
ChEBI ID3440
PubChem Compound ID10364
Kegg Compound IDC09840
YMDB IDYMDB01647
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21447440
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21544887
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21815724
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21879312
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21938469
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22002497
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22129102
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22139435
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22183117
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22273461
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22289589
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22305883
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22308777
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22328722
15. Alali F, Al-Lafi T: GC-MS analysis and bioactivity testing of the volatile oil from the leaves of the toothbrush tree Salvadora persica L. Nat Prod Res. 2003 Jun;17(3):189-94.
16. Bekhechi C, Boti JB, Bekkara FA, Abdelouahid DE, Casanova J, Tomi F: Isothymol in Ajowan essential oil. Nat Prod Commun. 2010 Jul;5(7):1107-10.
17. Rashid KA, Mumma RO: Screening pesticides for their ability to damage bacterial DNA. J Environ Sci Health B. 1986 Aug;21(4):319-34.
18. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
19. 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.
20. 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.
21. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
22. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
23. The lipid handbook with CD-ROM