p-MENTH-1,4(8)-DIEN-3-ONE
Relevant Data
Food Additives Approved in the United States
Flavouring Substances Approved by European Union:
General Information
| Synonyms: | 1-METHYL-4-ISOPROPYLIDENE-1-CYCLOHEXEN-3-ONE, PIPERITENONE |
| Chemical Names: | 3-METHYL-6-(1-METHYLETHYLIDENE)CYCLOHEX-2-EN-1-ONE |
| CAS number: | 491-09-8 |
| COE number: | 11189 |
| JECFA number: | 757 |
| FEMA number: | 3560 |
| Functional Class: |
Flavouring Agent FLAVOURING_AGENT |
From apps.who.int
Evaluations
| Evaluation year: | 2000 |
| ADI: | No safety concern at current levels of intake when used as a flavouring agent |
| Report: | TRS 901-JECFA 55/56 |
| Tox Monograph: | FAS 46-JECFA 55/221 |
| Specification: | COMPENDIUM ADDENDUM 8/FNP 52 Add.8/176 |
From apps.who.int
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 381152 |
| IUPAC Name | 3-methyl-6-propan-2-ylidenecyclohex-2-en-1-one |
| InChI | InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6H,4-5H2,1-3H3 |
| InChI Key | HKZQJZIFODOLFR-UHFFFAOYSA-N |
| Canonical SMILES | CC1=CC(=O)C(=C(C)C)CC1 |
| Molecular Formula | C10H14O |
| Wikipedia | piperitenone |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 150.221 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 240.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B w I A A A A A A A A A A A A A A A A A A A A A A A A A A g A A A A A A A A A A A A A A A A G g A A A A A A D A S A g A A C A A A A A A C I A q B S A A A A A A A g A A A A C A E A A E g A A B I A A Q A A A A A A g A A I A Q M I i A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 17.1 |
| Monoisotopic Mass | 150.104 |
| Exact Mass | 150.104 |
| XLogP3 | None |
| XLogP3-AA | 2.2 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 11 |
| 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 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9029 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.8271 |
| P-glycoprotein Substrate | Non-substrate | 0.5849 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.5207 |
| Non-inhibitor | 0.8663 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7936 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4203 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8145 |
| CYP450 2D6 Substrate | Non-substrate | 0.7792 |
| CYP450 3A4 Substrate | Substrate | 0.6031 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5562 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8833 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9119 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8188 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9664 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7458 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8273 |
| Non-inhibitor | 0.8991 | |
| AMES Toxicity | Non AMES toxic | 0.9378 |
| Carcinogens | Non-carcinogens | 0.8100 |
| Fish Toxicity | High FHMT | 0.8179 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.5513 |
| Honey Bee Toxicity | High HBT | 0.8562 |
| Biodegradation | Ready biodegradable | 0.7487 |
| Acute Oral Toxicity | III | 0.8168 |
| Carcinogenicity (Three-class) | Non-required | 0.5395 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.6310 | LogS |
| Caco-2 Permeability | 2.1234 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8246 | LD50, mol/kg |
| Fish Toxicity | 1.4619 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.2654 | pIGC50, ug/L |
From admetSAR
Taxonomic Classification
| 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 - Quinomethane - O-quinomethane - Cyclohexenone - Cyclic ketone - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - 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. |
From ClassyFire