Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:32:31 UTC
Update Date2022-03-07 02:55:41 UTC
HMDB IDHMDB0038256
Secondary Accession Numbers
  • HMDB38256
Metabolite Identification
Common NameGeranyl acetoacetate
DescriptionGeranyl acetoacetate belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Based on a literature review a small amount of articles have been published on Geranyl acetoacetate.
Structure
Data?1563863166
Synonyms
ValueSource
Geranyl acetoacetic acidGenerator
(e)-3,7-Dimethyl-2,6-octadienyl 3-oxobutanoateHMDB
(e)-3,7-Dimethyl-2,6-octadienyl acetoacetateHMDB
3,7-Dimethyl-2,6-octadienyl ester(e)-acetoacetic acidHMDB
Acetoacetic acid, 3,7-dimethyl-2,6-octadienyl esterHMDB
FEMA 2510HMDB
Geranyl 3-oxobutanoateHMDB
Geranyl beta-ketobutyrateHMDB
trans-3,7-Dimethyl-2,6-octadien-1-yl 3-oxobutanoateHMDB
trans-3,7-Dimethyl-2,6-octadien-1-yl acetoacetateHMDB
Chemical FormulaC14H22O3
Average Molecular Weight238.3227
Monoisotopic Molecular Weight238.15689457
IUPAC Name(2Z)-3,7-dimethylocta-2,6-dien-1-yl 3-oxobutanoate
Traditional Name(2Z)-3,7-dimethylocta-2,6-dien-1-yl 3-oxobutanoate
CAS Registry Number10032-00-5
SMILES
CC(=O)CC(=O)OC\C=C(\C)CCC=C(C)C
InChI Identifier
InChI=1S/C14H22O3/c1-11(2)6-5-7-12(3)8-9-17-14(16)10-13(4)15/h6,8H,5,7,9-10H2,1-4H3/b12-8-
InChI KeyRYILZWKGLGVPOC-WQLSENKSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohol esters
Direct ParentFatty alcohol esters
Alternative Parents
Substituents
  • Fatty alcohol ester
  • Acyclic monoterpenoid
  • Monoterpenoid
  • Beta-keto acid
  • Fatty acid ester
  • 1,3-dicarbonyl compound
  • Keto acid
  • Carboxylic acid ester
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point127.00 to 129.00 °C. @ 22.00 mm HgThe Good Scents Company Information System
Water Solubility33.71 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.517 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP3.7ALOGPS
logP3.17ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)10.39ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity70.23 m³·mol⁻¹ChemAxon
Polarizability27.25 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+159.40931661259
DarkChem[M-H]-156.79731661259
DeepCCS[M+H]+156.40430932474
DeepCCS[M-H]-154.04630932474
DeepCCS[M-2H]-187.08530932474
DeepCCS[M+Na]+162.49730932474
AllCCS[M+H]+160.732859911
AllCCS[M+H-H2O]+157.332859911
AllCCS[M+NH4]+163.832859911
AllCCS[M+Na]+164.732859911
AllCCS[M-H]-161.332859911
AllCCS[M+Na-2H]-162.232859911
AllCCS[M+HCOO]-163.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Geranyl acetoacetateCC(=O)CC(=O)OC\C=C(\C)CCC=C(C)C2206.6Standard polar33892256
Geranyl acetoacetateCC(=O)CC(=O)OC\C=C(\C)CCC=C(C)C1564.0Standard non polar33892256
Geranyl acetoacetateCC(=O)CC(=O)OC\C=C(\C)CCC=C(C)C1720.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Geranyl acetoacetate,1TMS,isomer #1CC(C)=CCC/C(C)=C\COC(=O)C=C(C)O[Si](C)(C)C1832.2Semi standard non polar33892256
Geranyl acetoacetate,1TMS,isomer #1CC(C)=CCC/C(C)=C\COC(=O)C=C(C)O[Si](C)(C)C1856.1Standard non polar33892256
Geranyl acetoacetate,1TMS,isomer #2C=C(CC(=O)OC/C=C(/C)CCC=C(C)C)O[Si](C)(C)C1790.7Semi standard non polar33892256
Geranyl acetoacetate,1TMS,isomer #2C=C(CC(=O)OC/C=C(/C)CCC=C(C)C)O[Si](C)(C)C1802.3Standard non polar33892256
Geranyl acetoacetate,1TBDMS,isomer #1CC(C)=CCC/C(C)=C\COC(=O)C=C(C)O[Si](C)(C)C(C)(C)C2068.3Semi standard non polar33892256
Geranyl acetoacetate,1TBDMS,isomer #1CC(C)=CCC/C(C)=C\COC(=O)C=C(C)O[Si](C)(C)C(C)(C)C2060.5Standard non polar33892256
Geranyl acetoacetate,1TBDMS,isomer #2C=C(CC(=O)OC/C=C(/C)CCC=C(C)C)O[Si](C)(C)C(C)(C)C2015.3Semi standard non polar33892256
Geranyl acetoacetate,1TBDMS,isomer #2C=C(CC(=O)OC/C=C(/C)CCC=C(C)C)O[Si](C)(C)C(C)(C)C1994.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Geranyl acetoacetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ku-9700000000-464bbd7934d9173adbaf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Geranyl acetoacetate 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 - Geranyl acetoacetate 10V, Positive-QTOFsplash10-000i-4790000000-97db0649e83f5b5bae962017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranyl acetoacetate 20V, Positive-QTOFsplash10-000i-9500000000-640dd734c70bcee51f772017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranyl acetoacetate 40V, Positive-QTOFsplash10-0670-9100000000-90966489ab2f1b35805b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranyl acetoacetate 10V, Negative-QTOFsplash10-0019-8690000000-16ea337a0db3b28e6a312017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranyl acetoacetate 20V, Negative-QTOFsplash10-0pc0-9700000000-d0f333fc4eb48adf94232017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranyl acetoacetate 40V, Negative-QTOFsplash10-0a4i-9300000000-bc23db33f8ce067ee6a42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranyl acetoacetate 10V, Negative-QTOFsplash10-0udi-1920000000-b22cd9cb2907b32770972021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranyl acetoacetate 20V, Negative-QTOFsplash10-0zfr-9700000000-47320c01017af31ea1e42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranyl acetoacetate 40V, Negative-QTOFsplash10-0a70-9500000000-de1c444d4d58dee8b2612021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranyl acetoacetate 10V, Positive-QTOFsplash10-001i-9600000000-b004eca92447f1950afe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranyl acetoacetate 20V, Positive-QTOFsplash10-001i-9400000000-1414a7dc914c2216b61f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Geranyl acetoacetate 40V, Positive-QTOFsplash10-0aou-9300000000-37319bd69b0189d414102021-09-22Wishart 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 IDFDB017550
KNApSAcK IDNot Available
Chemspider ID30777244
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound54611954
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1024841
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.