Terpinolene
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Basic Info
| Common Name | Terpinolene(F05620) |
| 2D Structure | |
| Description | Terpinolene is found in allspice. Terpinolene is a constituent of many essential oils e.g. Citrus, Mentha, Juniperus, Myristica species Parsnip oil (Pastinaca sativa) is a major source (40-70%). Terpinolene is a flavouring ingredient. Terpinolene has been shown to exhibit anti-fungal function (A7932). |
| FRCD ID | F05620 |
| CAS Number | 586-62-9 |
| PubChem CID | 11463 |
| Formula | C10H16 |
| IUPAC Name | 1-methyl-4-propan-2-ylidenecyclohexene |
| InChI Key | MOYAFQVGZZPNRA-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4H,5-7H2,1-3H3 |
| Canonical SMILES | CC1=CCC(=C(C)C)CC1 |
| Isomeric SMILES | CC1=CCC(=C(C)C)CC1 |
| Synonyms |
4-Isopropylidene-1-methylcyclohexene
TERPINOLENE
586-62-9
Isoterpinene
Terpinolen
alpha-Terpinolene
1,4(8)-p-Menthadiene
p-Mentha-1,4(8)-diene
Tereben
p-Menth-1,4(8)-diene
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Prenol lipids |
| Subclass | Monoterpenoids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Menthane monoterpenoids |
| Alternative Parents | |
| Molecular Framework | Aliphatic homomonocyclic compounds |
| Substituents | P-menthane monoterpenoid - Monocyclic monoterpenoid - Branched unsaturated hydrocarbon - Cycloalkene - Cyclic olefin - Unsaturated aliphatic hydrocarbon - Unsaturated hydrocarbon - Olefin - Hydrocarbon - Aliphatic homomonocyclic compound |
| Description | This compound 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 136.238 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 0 |
| Rotatable Bond Count | 0 |
| Complexity | 178 |
| Monoisotopic Mass | 136.125 |
| Exact Mass | 136.125 |
| XLogP | 2.8 |
| Formal Charge | 0 |
| Heavy Atom Count | 10 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9299 |
| Human Intestinal Absorption | HIA+ | 0.9963 |
| Caco-2 Permeability | Caco2+ | 0.7302 |
| P-glycoprotein Substrate | Non-substrate | 0.5815 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8033 |
| Non-inhibitor | 0.7709 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7921 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.4834 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8464 |
| CYP450 2D6 Substrate | Non-substrate | 0.8029 |
| CYP450 3A4 Substrate | Non-substrate | 0.5324 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7845 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8961 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9479 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8944 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9482 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7288 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8209 |
| Non-inhibitor | 0.8438 | |
| AMES Toxicity | Non AMES toxic | 0.9182 |
| Carcinogens | Non-carcinogens | 0.6580 |
| Fish Toxicity | High FHMT | 0.9766 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9947 |
| Honey Bee Toxicity | High HBT | 0.8185 |
| Biodegradation | Ready biodegradable | 0.7561 |
| Acute Oral Toxicity | III | 0.7058 |
| Carcinogenicity (Three-class) | Warning | 0.5287 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.1883 | LogS |
| Caco-2 Permeability | 1.7364 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.4605 | LD50, mol/kg |
| Fish Toxicity | -0.4680 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.1998 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Fumigant and repellent activities of essential oil extracted from Artemisia dubiaand its main compounds against two stored product pests. | Nat Prod Res | 2018 May | 28532258 |
| Identification of highly effective antitrypanosomal compounds in essential oilsfrom the Apiaceae family. | Ecotoxicol Environ Saf | 2018 Jul 30 | 29549739 |
| The crop-residue of fiber hemp cv. Futura 75: from a waste product to a source ofbotanical insecticides. | Environ Sci Pollut Res Int | 2018 Apr | 29105041 |
| Chemical composition and antibiofilm activity of Petroselinum crispum and Ocimum basilicum essential oils against Vibrio spp. strains. | Microb Pathog | 2016 Jan | 26596707 |
| Empirical prediction and validation of antibacterial inhibitory effects ofvarious plant essential oils on common pathogenic bacteria. | Int J Food Microbiol | 2015 Jun 2 | 25764982 |
| Antiulcerogenic and antibacterial activities of Apium graveolens essential oiland extract. | Nat Prod Res | 2013 | 22934666 |
| Chemoprevention by essential oil of turmeric leaves (Curcuma longa L.) on the growth of Aspergillus flavus and aflatoxin production. | Food Chem Toxicol | 2011 May | 21354246 |
| Chemical composition and antibacterial, antifungal and antioxidant activities of the flower oil of Retama raetam (Forssk.) Webb from Tunisia. | Nat Prod Res | 2010 May | 20461625 |
| Repellency of essential oils of Cryptomeria japonica (Pinaceae) against adults ofthe mosquitoes Aedes aegypti and Aedes albopictus (Diptera:Culicidae). | J Agric Food Chem | 2009 Dec 9 | 19902948 |
| Antioxidative properties of the essential oil from Pinus mugo. | J Agric Food Chem | 2003 Dec 17 | 14664510 |
| Volatile components of green walnut husks. | J Agric Food Chem | 2000 Jul | 10898636 |
| Encapsulation of lemon oil by paste method using beta-cyclodextrin: encapsulationefficiency and profile of oil volatiles. | J Agric Food Chem | 1999 Dec | 10606594 |
| Larvicidal Activity of Essential Oils of Five Apiaceae Taxa and Some of TheirMain Constituents Against Culex quinquefasciatus. | None | None | 28990348 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]