Showing Compound Card for alpha-Terpinene-4-ol (CDB000303)

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Record Information
Version1.0
Created at2020-03-19 00:29:53 UTC
Updated at2020-12-07 19:07:20 UTC
CannabisDB IDCDB000303
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namealpha-Terpinene-4-ol
Descriptionα-Terpinene-4-ol, also known as terpinen-4-ol, 1-para-menthen-4-ol or p-Menth-1-en-4-ol or 4-carvomenthenol, is an isomer of terpineol. It belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. α-Terpinene-4-ol is a hydrophobic, largely neutral molecule that is essentially insoluble in water. It has a peppery, spicy, musty, citrus odor and a cooling woody or spicy taste. α-Terpinene-4-ol is widely used as a flavoring agent and as a masking agent in cosmetics. α-Terpinene-4-ol is a natural product that can be found in a number of plants, such as allspice, anise, apple, basil, cardamom, cinnamon and Melaleuca alternifolia (also called tea tree) and is the main bioactive component of tea tree oil (PMID 22083482 ). α-Terpinene-4-ol is also one of the monoterpenes found in cannabis plants (PMID: 6991645 ). Terpinen-4-ol is a potent bactericidal agent that also possess antifungal properties. In particular, it has shown in vitro activity against Staphylococcus aureus and C. albicans (PMID: 27275783 ). It has also been shown that combining this natural substance and conventional drugs may help treat resistant yeast and bacterial infections. Several studies have suggested that terpinen-4-ol induces antitumor effects by selectively causing necrotic cell death and cell-cycle arrest in melanoma cell lines, or by triggering caspase-dependent apoptosis in human melanoma cells (PMID: 27275783 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(+)-Terpinen-4-olHMDB
(S)-(+)-P-Menth-1-en-4-olHMDB
(S)-1-Isopropyl-4-methyl-3-cyclohexen-1-olHMDB
S-4-CarvomenthenolHMDB
S-OriganolHMDB
Chemical FormulaC10H18O
Average Molecular Weight154.25
Monoisotopic Molecular Weight154.1358
IUPAC Name(1S)-4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol
Traditional Name(1S)-1-isopropyl-4-methylcyclohex-3-en-1-ol
CAS Registry Number2438-10-0
SMILES
CC(C)[C@]1(O)CCC(C)=CC1
InChI Identifier
InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3/t10-/m1/s1
InChI KeyWRYLYDPHFGVWKC-SNVBAGLBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Tertiary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.81ALOGPS
logP2.33ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)20ChemAxon
pKa (Strongest Basic)-0.61ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.31 m³·mol⁻¹ChemAxon
Polarizability18.7 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-MSalpha-Terpinene-4-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014l-9200000000-dad36a705047932a9123Spectrum
Predicted GC-MSalpha-Terpinene-4-ol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01xc-9310000000-a2afa37a32f9557366b3Spectrum
Predicted GC-MSalpha-Terpinene-4-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-ed4d73b62c9007b43a392016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-6900000000-6b9711b4c87ceef37b0e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0le9-9200000000-fc62c06aa902f1d8e2732016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-5ef88141faef90e303ea2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-d05510ef6d4b5d914c822016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f80-7900000000-82e827bc01f85059523c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-8900000000-442df4d2c1c1a44d9f262021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0015-9300000000-08286b81fc833490c00b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-d2fb56949f102920a8d52021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-d2363ae8d4dbdcccda802021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-317e3f90e7716a16fe352021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9800000000-e9742125cfbf7b82348a2021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0035823
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014586
KNApSAcK IDC00010928
Chemspider ID2006320
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2724161
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Hammer KA, Carson CF, Riley TV: Effects of Melaleuca alternifolia (tea tree) essential oil and the major monoterpene component terpinen-4-ol on the development of single- and multistep antibiotic resistance and antimicrobial susceptibility. Antimicrob Agents Chemother. 2012 Feb;56(2):909-15. doi: 10.1128/AAC.05741-11. Epub 2011 Nov 14. [PubMed:22083482 ]
  3. Shapira S, Pleban S, Kazanov D, Tirosh P, Arber N: Terpinen-4-ol: A Novel and Promising Therapeutic Agent for Human Gastrointestinal Cancers. PLoS One. 2016 Jun 8;11(6):e0156540. doi: 10.1371/journal.pone.0156540. eCollection 2016. [PubMed:27275783 ]
  4. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  5. Su CW, Tighe S, Sheha H, Cheng AMS, Tseng SCG: Safety and efficacy of 4-terpineol against microorganisms associated with blepharitis and common ocular diseases. BMJ Open Ophthalmol. 2018 Jun 4;3(1):e000094. doi: 10.1136/bmjophth-2017-000094. eCollection 2018. [PubMed:30123842 ]
  6. Ramage G, Milligan S, Lappin DF, Sherry L, Sweeney P, Williams C, Bagg J, Culshaw S: Antifungal, cytotoxic, and immunomodulatory properties of tea tree oil and its derivative components: potential role in management of oral candidosis in cancer patients. Front Microbiol. 2012 Jun 18;3:220. doi: 10.3389/fmicb.2012.00220. eCollection 2012. [PubMed:22719736 ]
  7. Tighe S, Gao YY, Tseng SC: Terpinen-4-ol is the Most Active Ingredient of Tea Tree Oil to Kill Demodex Mites. Transl Vis Sci Technol. 2013 Nov;2(7):2. doi: 10.1167/tvst.2.7.2. Epub 2013 Nov 13. [PubMed:24349880 ]