Terpinyl Isobutyrate

Basic Info

Common NameTerpinyl Isobutyrate(F08629)
2D Structure
FRCD IDF08629
CAS Number7774-65-4
PubChem CID522673
FormulaC14H24O2
IUPAC Name

2-(4-methylcyclohex-3-en-1-yl)propan-2-yl 2-methylpropanoate

InChI Key

SMQUXKIIXFOJKI-UHFFFAOYSA-N

InChI

InChI=1S/C14H24O2/c1-10(2)13(15)16-14(4,5)12-8-6-11(3)7-9-12/h6,10,12H,7-9H2,1-5H3

Canonical SMILES

CC1=CCC(CC1)C(C)(C)OC(=O)C(C)C

Isomeric SMILES

CC1=CCC(CC1)C(C)(C)OC(=O)C(C)C

WikipediaTerpinyl Isobutyrate
Synonyms
        
            Terpinyl isobutyrate
        
            7774-65-4
        
            P-Menth-1-en-8-yl isobutyrate
        
            FEMA No. 3050
        
            alpha-terpinyl isobutyrate
        
            EINECS 231-878-5
        
            BRN 3129659
        
            .alpha.-Terpinyl isobutyrate
        
            1-Methyl-1-(4-methyl-3-cyclohexen-1-yl)ethyl 2-methylpropanoate
        
            Propanoic acid, 2-methyl-, 1-methyl-1-(4-methyl-3-cyclohexen-1-yl)ethyl ester
Classifies
                

                  
                    Food Additive
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassPrenol lipids
SubclassMonoterpenoids
Intermediate Tree NodesNot available
Direct ParentMenthane monoterpenoids
Alternative Parents
Molecular FrameworkAliphatic homomonocyclic compounds
SubstituentsP-menthane monoterpenoid - Monocyclic monoterpenoid - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic homomonocyclic compound
DescriptionThis 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 NameProperty Value
Molecular Weight224.344
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count4
Complexity287
Monoisotopic Mass224.178
Exact Mass224.178
XLogP3.5
Formal Charge0
Heavy Atom Count16
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9429
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.7264
P-glycoprotein SubstrateNon-substrate0.5155
P-glycoprotein InhibitorNon-inhibitor0.6760
Inhibitor0.5970
Renal Organic Cation TransporterNon-inhibitor0.8197
Distribution
Subcellular localizationMitochondria0.6558
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8647
CYP450 2D6 SubstrateNon-substrate0.9042
CYP450 3A4 SubstrateSubstrate0.6255
CYP450 1A2 InhibitorNon-inhibitor0.8316
CYP450 2C9 InhibitorNon-inhibitor0.7372
CYP450 2D6 InhibitorNon-inhibitor0.9325
CYP450 2C19 InhibitorNon-inhibitor0.5656
CYP450 3A4 InhibitorNon-inhibitor0.9003
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7554
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9332
Non-inhibitor0.8681
AMES ToxicityNon AMES toxic0.9426
CarcinogensNon-carcinogens0.6462
Fish ToxicityHigh FHMT0.9352
Tetrahymena Pyriformis ToxicityHigh TPT0.9467
Honey Bee ToxicityHigh HBT0.8786
BiodegradationReady biodegradable0.7716
Acute Oral ToxicityIII0.7462
Carcinogenicity (Three-class)Non-required0.4913
Model Value Unit
Absorption
Aqueous solubility-3.7837LogS
Caco-2 Permeability1.5843LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.6185LD50, mol/kg
Fish Toxicity0.6080pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.1089pIGC50, ug/L