L-MENTHYL (R,S)-3-HYDROXYBUTYRATE (CHEM006417)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:13:26 UTC
Update Date2016-11-09 01:09:44 UTC
Accession NumberCHEM006417
Identification
Common NameL-MENTHYL (R,S)-3-HYDROXYBUTYRATE
ClassSmall Molecule
DescriptionL-Menthyl (R,S)-3-hydroxybutyrate is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]")
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
L-Menthyl (R,S)-3-hydroxybutyric acidGenerator
3-(2-Carboxyethyl)-2-methylbenzothiazolium bromideHMDB
3-(2-Carboxyethyl)-2-methylbenzothiozolium bromideHMDB
Benzothiazolium, 3-(2-carboxyethyl)-2-methyl-, bromideHMDB
(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 3-hydroxybutanoic acidGenerator
Chemical FormulaC14H26O3
Average Molecular Mass242.354 g/mol
Monoisotopic Mass242.188 g/mol
CAS Registry Number374629-79-5
IUPAC Name(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl 3-hydroxybutanoate
Traditional Name(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 3-hydroxybutanoate
SMILESCC(O)CC(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C
InChI IdentifierInChI=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/t10-,11?,12+,13-/m1/s1
InChI KeyXSJPRWBZLUYOOI-IBSWDFHHSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
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
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.98ALOGPS
logP2.94ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)15.41ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity67.42 m³·mol⁻¹ChemAxon
Polarizability28.64 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054x-9210000000-c565198613d639d1f9d7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9410000000-ad4b0e8ac0909350819aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-2690000000-ceae3deb60a592b5d7d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-4920000000-5dcfe876523ff927babdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-4900000000-8d1c2c2faf0f8f47d27eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4l-0950000000-55d04d133fec770b2d0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9600000000-d6d78d008d2d7611aa01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9800000000-782a881e4e8e68c24369Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2390000000-e8a0221c61a25ee63a95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-9830000000-00bf223b26463cb568d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066r-9300000000-d8f4466e43e928b5c56dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9100000000-e5069dfeb3c456c01452Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9200000000-7268b69df44b3a6a8e68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xv-9000000000-ae9a1157fd520cb647a7Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0032370
FooDB IDFDB009784
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8395936
ChEBI IDNot Available
PubChem Compound ID10220444
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. EAFUS: Everything Added to Food in the United States.
6. The lipid handbook with CD-ROM