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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:51:39 UTC
Update Date2021-10-13 06:51:53 UTC
HMDB IDHMDB0035837
Secondary Accession Numbers
  • HMDB35837
Metabolite Identification
Common NameCitronellic acid
DescriptionCitronellic acid, also known as rhodinic acid or rhodinate, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Based on a literature review a significant number of articles have been published on Citronellic acid.
Structure
Data?1563862779
Synonyms
ValueSource
3,7-Dimethyl-6-octenoic acidChEBI
Rhodinic acidChEBI
Rhodinolic acidChEBI
3,7-Dimethyl-6-octenoateGenerator
RhodinateGenerator
RhodinolateGenerator
CitronellateGenerator
CallitrolHMDB
FEMA 3142HMDB
Chemical FormulaC10H18O2
Average Molecular Weight170.2487
Monoisotopic Molecular Weight170.13067982
IUPAC Name3,7-dimethyloct-6-enoic acid
Traditional Namecitronellic acid
CAS Registry Number502-47-6
SMILES
CC(CCC=C(C)C)CC(O)=O
InChI Identifier
InChI=1S/C10H18O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,9H,4,6-7H2,1-3H3,(H,11,12)
InChI KeyGJWSUKYXUMVMGX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAcyclic monoterpenoids
Alternative Parents
Substituents
  • Acyclic monoterpenoid
  • Medium-chain fatty acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Unsaturated fatty acid
  • Fatty acyl
  • Fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point257 °CNot Available
Boiling Point121.00 to 122.00 °C. @ 1.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP3.159 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.74 g/LALOGPS
logP10(2.88) g/LALOGPS
logP10(2.87) g/LChemAxon
logS10(-2) g/LALOGPS
pKa (Strongest Acidic)5.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity50.22 m³·mol⁻¹ChemAxon
Polarizability20.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.68831661259
DarkChem[M-H]-140.24431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Citronellic acidCC(CCC=C(C)C)CC(O)=O2224.9Standard polar33892256
Citronellic acidCC(CCC=C(C)C)CC(O)=O1257.0Standard non polar33892256
Citronellic acidCC(CCC=C(C)C)CC(O)=O1327.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Citronellic acid,1TMS,isomer #1CC(C)=CCCC(C)CC(=O)O[Si](C)(C)C1389.9Semi standard non polar33892256
Citronellic acid,1TBDMS,isomer #1CC(C)=CCCC(C)CC(=O)O[Si](C)(C)C(C)(C)C1615.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Citronellic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9400000000-b4a9a30bedbf4a8752e32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citronellic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00vr-9410000000-066c428f2bfcc666edb62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citronellic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellic acid 10V, Positive-QTOFsplash10-0udi-0900000000-ca88f25a99f1a223f1362015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellic acid 20V, Positive-QTOFsplash10-004i-4900000000-ed381ce7b92f7d2c7f5d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellic acid 40V, Positive-QTOFsplash10-066u-9100000000-c5932ee6d660873f708b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellic acid 10V, Positive-QTOFsplash10-0udi-0900000000-ca88f25a99f1a223f1362015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellic acid 20V, Positive-QTOFsplash10-004i-4900000000-ed381ce7b92f7d2c7f5d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellic acid 40V, Positive-QTOFsplash10-066u-9100000000-c5932ee6d660873f708b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellic acid 10V, Negative-QTOFsplash10-016r-0900000000-19fc1189fe21eeab9c322015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellic acid 20V, Negative-QTOFsplash10-0fvi-1900000000-80b43a00c664236457612015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellic acid 40V, Negative-QTOFsplash10-0a4i-9600000000-cf125975f8a7d51e6fd72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellic acid 10V, Negative-QTOFsplash10-016r-0900000000-19fc1189fe21eeab9c322015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellic acid 20V, Negative-QTOFsplash10-0fvi-1900000000-80b43a00c664236457612015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellic acid 40V, Negative-QTOFsplash10-0a4i-9600000000-cf125975f8a7d51e6fd72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellic acid 10V, Positive-QTOFsplash10-069r-9500000000-5b614443aca15fd843882021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellic acid 20V, Positive-QTOFsplash10-00lr-9000000000-4d49025f717218ec8e942021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellic acid 40V, Positive-QTOFsplash10-00kf-9000000000-6e63db0f2c5eb898d40c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellic acid 10V, Negative-QTOFsplash10-014i-0900000000-63f63b3bb1be8f4b50a82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellic acid 20V, Negative-QTOFsplash10-00vi-0900000000-a09fcd57c7d1f620775f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citronellic acid 40V, Negative-QTOFsplash10-052f-9100000000-7746992104a9e11768a62021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014607
KNApSAcK IDC00010311
Chemspider ID9973
KEGG Compound IDC16462
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10402
PDB IDNot Available
ChEBI ID80507
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1020681
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.