Relevant Data

Food Additives Approved in the United States


General Information

Chemical Names: L-MENTHYL (R,S)-3-HYDROXYBUTYRATE
CAS number: 108766-16-1
JECFA number: 1855
FEMA number: 4308
Functional Class: Flavouring Agent
FLAVOURING_AGENT

From apps.who.int


Evaluations

Evaluation year: 2008
ADI: No safety concern at current levels of intake when used as a flavouring agent
Meeting: 69
Specs Code: N
Report: RS 952-JECFA 69/141
Tox Monograph: FAS 60-JECFA 69/626
Specification: FAO JECFA Monographs 5/101

From apps.who.int


Computed Descriptors

Download SDF
2D Structure
CID11586787
IUPAC Name(5-methyl-2-propan-2-ylcyclohexyl) 3-hydroxybutanoate
InChIInChI=1S/C14H26O3/c1-9(2)12-6-5-10(3)7-13(12)17-14(16)8-11(4)15/h9-13,15H,5-8H2,1-4H3
InChI KeyXSJPRWBZLUYOOI-UHFFFAOYSA-N
Canonical SMILESCC1CCC(C(C1)OC(=O)CC(C)O)C(C)C
Molecular FormulaC14H26O3

From Pubchem


Computed Properties

Property Name Property Value
Molecular Weight242.359
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count5
Complexity250.0
CACTVS Substructure Key Fingerprint A A A D c e B w M 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 w A A A A A A A A A A A A A A A A G g A A C A A A D R S g g A I C C A A A B g A I A A C Q C A A A A A A A A A A A A A E A A A A A E B Y A A A A C Q A A F I A A A A A G A w P A O g A A A A A A A A A C A A A I A A B A A A A A A A A A A A A = =
Topological Polar Surface Area46.5
Monoisotopic Mass242.188
Exact Mass242.188
XLogP3None
XLogP3-AA3.3
Compound Is CanonicalizedTrue
Formal Charge0
Heavy Atom Count17
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count4
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

From Pubchem


ADMET Predicted Profile --- Classification

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.8945
Human Intestinal AbsorptionHIA+0.9887
Caco-2 PermeabilityCaco2+0.7340
P-glycoprotein SubstrateNon-substrate0.5548
P-glycoprotein InhibitorNon-inhibitor0.7544
Non-inhibitor0.5755
Renal Organic Cation TransporterNon-inhibitor0.8762
Distribution
Subcellular localizationMitochondria0.8587
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8106
CYP450 2D6 SubstrateNon-substrate0.8634
CYP450 3A4 SubstrateSubstrate0.5226
CYP450 1A2 InhibitorNon-inhibitor0.9187
CYP450 2C9 InhibitorNon-inhibitor0.8434
CYP450 2D6 InhibitorNon-inhibitor0.9394
CYP450 2C19 InhibitorNon-inhibitor0.8675
CYP450 3A4 InhibitorNon-inhibitor0.8962
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9787
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9093
Non-inhibitor0.8851
AMES ToxicityNon AMES toxic0.7647
CarcinogensNon-carcinogens0.8327
Fish ToxicityHigh FHMT0.9665
Tetrahymena Pyriformis ToxicityHigh TPT0.9975
Honey Bee ToxicityHigh HBT0.8027
BiodegradationNot ready biodegradable0.7828
Acute Oral ToxicityIII0.6332
Carcinogenicity (Three-class)Non-required0.7351

From admetSAR


ADMET Predicted Profile --- Regression

Model Value Unit
Absorption
Aqueous solubility-3.9360LogS
Caco-2 Permeability1.1689LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.1793LD50, mol/kg
Fish Toxicity1.0958pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.5476pIGC50, ug/L

From admetSAR


Taxonomic Classification

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 - Beta-hydroxy acid - Fatty acid ester - Fatty acyl - Hydroxy acid - Carboxylic acid ester - Secondary alcohol - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Hydrocarbon derivative - Organic oxide - Alcohol - Carbonyl group - Organic oxygen compound - Organooxygen compound - 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.

From ClassyFire