Menthyl Acetate

Basic Info

Common NameMenthyl Acetate(F08836)
2D Structure
FRCD IDF08836
CAS Number16409-45-3
PubChem CID27867
FormulaC12H22O2
IUPAC Name

(5-methyl-2-propan-2-ylcyclohexyl) acetate

InChI Key

XHXUANMFYXWVNG-UHFFFAOYSA-N

InChI

InChI=1S/C12H22O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h8-9,11-12H,5-7H2,1-4H3

Canonical SMILES

CC1CCC(C(C1)OC(=O)C)C(C)C

Isomeric SMILES

CC1CCC(C(C1)OC(=O)C)C(C)C

WikipediaMenthyl Acetate
Synonyms
        
            Menthyl acetate
        
            Menthol, acetate
        
            Menthyl acetate racemic
        
            (-)-Menthyl acetate
        
            FEMA Number 2668
        
            89-48-5
        
            HSDB 824
        
            16409-45-3
        
            Neomenthyl acetate
        
            Cyclohexanol, 5-methyl-2-(1-methylethyl)-, acetate
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 Weight198.306
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Complexity199
Monoisotopic Mass198.162
Exact Mass198.162
XLogP3.6
Formal Charge0
Heavy Atom Count14
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count3
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9490
Human Intestinal AbsorptionHIA+0.9970
Caco-2 PermeabilityCaco2+0.8219
P-glycoprotein SubstrateNon-substrate0.6842
P-glycoprotein InhibitorNon-inhibitor0.7406
Non-inhibitor0.8852
Renal Organic Cation TransporterNon-inhibitor0.8355
Distribution
Subcellular localizationMitochondria0.8305
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8260
CYP450 2D6 SubstrateNon-substrate0.8294
CYP450 3A4 SubstrateSubstrate0.5972
CYP450 1A2 InhibitorNon-inhibitor0.8324
CYP450 2C9 InhibitorNon-inhibitor0.9097
CYP450 2D6 InhibitorNon-inhibitor0.9375
CYP450 2C19 InhibitorNon-inhibitor0.8249
CYP450 3A4 InhibitorNon-inhibitor0.9496
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9652
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8859
Non-inhibitor0.8557
AMES ToxicityNon AMES toxic0.7554
CarcinogensNon-carcinogens0.7766
Fish ToxicityHigh FHMT0.9328
Tetrahymena Pyriformis ToxicityHigh TPT0.6800
Honey Bee ToxicityHigh HBT0.8286
BiodegradationReady biodegradable0.5814
Acute Oral ToxicityIV0.5253
Carcinogenicity (Three-class)Non-required0.6467
Model Value Unit
Absorption
Aqueous solubility-3.5664LogS
Caco-2 Permeability1.5353LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.4463LD50, mol/kg
Fish Toxicity1.0655pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.9037pIGC50, ug/L

References

TitleJournalDatePubmed ID
Phytochemical residue profiles in rice grains fumigated with essential oils forthe control of rice weevil.PLoS One2017 Oct 1229023481
African peppermint (Mentha piperita) from Morocco: Chemical composition andantimicrobial properties of essential oil.J Adv Pharm Technol Res2017 Jul-Sep28795021
Biocontrol potential of essential oil monoterpenes against housefly, Muscadomestica (Diptera: Muscidae).Ecotoxicol Environ Saf2014 Feb24433784
Antioxidant and antibacterial effects of Lavandula and Mentha essential oils inminced beef inoculated with E. coli O157:H7 and S. aureus during storage at abuserefrigeration temperature.Meat Sci2012 Dec22789458
Development of quality assessment method for optically active food flavorchemicals.J AOAC Int2011 May-Jun21797021