L-MENTHYL (R,S)-3-HYDROXYBUTYRATE
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 | |
| CID | 11586787 |
| IUPAC Name | (5-methyl-2-propan-2-ylcyclohexyl) 3-hydroxybutanoate |
| InChI | InChI=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 Key | XSJPRWBZLUYOOI-UHFFFAOYSA-N |
| Canonical SMILES | CC1CCC(C(C1)OC(=O)CC(C)O)C(C)C |
| Molecular Formula | C14H26O3 |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 242.359 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 5 |
| Complexity | 250.0 |
| 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 Area | 46.5 |
| Monoisotopic Mass | 242.188 |
| Exact Mass | 242.188 |
| XLogP3 | None |
| XLogP3-AA | 3.3 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 17 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 4 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.8945 |
| Human Intestinal Absorption | HIA+ | 0.9887 |
| Caco-2 Permeability | Caco2+ | 0.7340 |
| P-glycoprotein Substrate | Non-substrate | 0.5548 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7544 |
| Non-inhibitor | 0.5755 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8762 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8587 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8106 |
| CYP450 2D6 Substrate | Non-substrate | 0.8634 |
| CYP450 3A4 Substrate | Substrate | 0.5226 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9187 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8434 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9394 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8675 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8962 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9787 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9093 |
| Non-inhibitor | 0.8851 | |
| AMES Toxicity | Non AMES toxic | 0.7647 |
| Carcinogens | Non-carcinogens | 0.8327 |
| Fish Toxicity | High FHMT | 0.9665 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9975 |
| Honey Bee Toxicity | High HBT | 0.8027 |
| Biodegradation | Not ready biodegradable | 0.7828 |
| Acute Oral Toxicity | III | 0.6332 |
| Carcinogenicity (Three-class) | Non-required | 0.7351 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.9360 | LogS |
| Caco-2 Permeability | 1.1689 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.1793 | LD50, mol/kg |
| Fish Toxicity | 1.0958 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.5476 | 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 - 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 |
| 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