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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:50:37 UTC
Update Date2021-10-13 06:51:45 UTC
HMDB IDHMDB0035820
Secondary Accession Numbers
  • HMDB35820
Metabolite Identification
Common Name(R)-Citronellal
Description(R)-Citronellal belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, (R)-citronellal is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on (R)-Citronellal.
Structure
Data?1563862776
Synonyms
ValueSource
(3R)-(+)-CitronellalChEBI
(3R)-3,7-Dimethyl-6-octenalChEBI
(R)-3,7-Dimethyl-6-octenalChEBI
(R)-3,7-Dimethyloct-6-enalChEBI
(+)-CitronellalHMDB
(3R)-3,7-Dimethyloct-6-enalHMDB
(R)-(+)-CitronellalHMDB
3,7-Dimethyl-(3R)-6-octenalHMDB
(R)-CitronellalPhytoBank
d-CitronellalPhytoBank
3,7-Dimethyl-6-octenalPhytoBank
(±)-CitronellalPhytoBank
2,3-DihydrocitralPhytoBank
2,6-Dimethylhept-5-enecarboxaldehydePhytoBank
3,7-Dimethyloct-6-en-1-alPhytoBank
RhodinalPhytoBank
dl-CitronellalPhytoBank
beta-CitronellalPhytoBank
β-CitronellalPhytoBank
Chemical FormulaC10H18O
Average Molecular Weight154.2493
Monoisotopic Molecular Weight154.135765198
IUPAC Name(3R)-3,7-dimethyloct-6-enal
Traditional Name(R)-(+)-citronellal
CAS Registry Number2385-77-5
SMILES
C[C@H](CCC=C(C)C)CC=O
InChI Identifier
InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3/t10-/m1/s1
InChI KeyNEHNMFOYXAPHSD-SNVBAGLBSA-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 aldehyde
  • Alpha-hydrogen aldehyde
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • 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 Point< 25 °CNot Available
Boiling Point207.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility38.94 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.83Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
logP10(3.25) g/LALOGPS
logP10(2.71) g/LChemAxon
logS10(-2.6) g/LALOGPS
pKa (Strongest Acidic)18.32ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity49.3 m³·mol⁻¹ChemAxon
Polarizability19.18 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.26231661259
DarkChem[M-H]-138.05331661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-CitronellalC[C@H](CCC=C(C)C)CC=O1491.4Standard polar33892256
(R)-CitronellalC[C@H](CCC=C(C)C)CC=O1125.3Standard non polar33892256
(R)-CitronellalC[C@H](CCC=C(C)C)CC=O1158.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-Citronellal,1TMS,isomer #1CC(C)=CCC[C@@H](C)C=CO[Si](C)(C)C1320.5Semi standard non polar33892256
(R)-Citronellal,1TMS,isomer #1CC(C)=CCC[C@@H](C)C=CO[Si](C)(C)C1303.5Standard non polar33892256
(R)-Citronellal,1TBDMS,isomer #1CC(C)=CCC[C@@H](C)C=CO[Si](C)(C)C(C)(C)C1540.1Semi standard non polar33892256
(R)-Citronellal,1TBDMS,isomer #1CC(C)=CCC[C@@H](C)C=CO[Si](C)(C)C(C)(C)C1522.8Standard non polar33892256
Spectra
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 IDFDB014582
KNApSAcK IDC00003037
Chemspider ID67959
KEGG Compound IDC09848
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound75427
PDB IDNot Available
ChEBI ID299
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1106481
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yoshida N, Takada T, Yamamura Y, Adachi I, Suzuki H, Kawakami J: Inhibitory effects of terpenoids on multidrug resistance-associated protein 2- and breast cancer resistance protein-mediated transport. Drug Metab Dispos. 2008 Jul;36(7):1206-11. doi: 10.1124/dmd.107.019513. Epub 2008 Apr 24. [PubMed:18436619 ]
  2. Yoshida N, Takagi A, Kitazawa H, Kawakami J, Adachi I: Effects of citronellal, a monoterpenoid in Zanthoxyli Fructus, on the intestinal absorption of digoxin in vitro and in vivo. J Pharm Sci. 2006 Mar;95(3):552-60. [PubMed:16419049 ]
  3. Chavan SP, Thakkar M, Jogdand GF, Kalkote UR: First enantiospecific synthesis of (-)-parvifoline and (-)-curcuquinone. J Org Chem. 2006 Nov 10;71(23):8986-8. [PubMed:17081038 ]
  4. Yoshida N, Koizumi M, Adachi I, Kawakami J: Inhibition of P-glycoprotein-mediated transport by terpenoids contained in herbal medicines and natural products. Food Chem Toxicol. 2006 Dec;44(12):2033-9. Epub 2006 Jul 10. [PubMed:16904803 ]
  5. Yoshida N, Takagi A, Kitazawa H, Kawakami J, Adachi I: Inhibition of P-glycoprotein-mediated transport by extracts of and monoterpenoids contained in Zanthoxyli fructus. Toxicol Appl Pharmacol. 2005 Dec 1;209(2):167-73. [PubMed:15890377 ]
  6. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  11. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.