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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:55 UTC
Update Date2019-07-23 06:09:39 UTC
HMDB IDHMDB0031846
Secondary Accession Numbers
  • HMDB31846
Metabolite Identification
Common NameGeranylacetone
DescriptionGeranylacetone, also known as fema 3542 or teprenone, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Geranylacetone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862179
Synonyms
ValueSource
(5E)-6,10-Dimethyl-5,9-undecadien-2-oneHMDB
(5E)-6,10-Dimethylundeca-5,9-dien-2-oneHMDB
(e)-6,10-Dimethyl-5,9- undecadien-2-oneHMDB
(e)-6,10-Dimethyl-5,9-undecadien-2-oneHMDB
(e)-6,10-Dimethylundeca-5,9-dien-2-oneHMDB
(e)-Geranyl acetoneHMDB
(e)-GeranylacetoneHMDB
6,10-Dimethyl-(5E)-5,9-undecadien-2-oneHMDB
6,10-Dimethyl-(e)-5,9-undecadien-2-oneHMDB
6,10-Dimethyl-5,9-undecadien-2-oneHMDB
6,10-Dimethyl-5,9-undecadien-2-one, (e)HMDB
6,10-Dimethyl-5,9-undecadiene-2-oneHMDB
6,10-Dimethyl-undecadien-2-oneHMDB
6,10-Dimethylundecadien-2-oneHMDB
DihydropseudoiononeHMDB
FEMA 3542HMDB
Geranyl acetoneHMDB
Geranyl-acetoneHMDB
GeranylacetonHMDB
GeranylgeranylacetoneHMDB
TeprenoneHMDB
trans-2,6-Dimethyl-2,6-undecadien-2-oneHMDB
trans-6,10-Dimethyl-5,9-undecadien-2-oneHMDB
trans-GeranylacetoneHMDB
NerylacetoneMeSH
Chemical FormulaC13H22O
Average Molecular Weight194.3132
Monoisotopic Molecular Weight194.167065326
IUPAC Name(5Z)-6,10-dimethylundeca-5,9-dien-2-one
Traditional Name(5Z)-6,10-dimethylundeca-5,9-dien-2-one
CAS Registry Number3796-70-1
SMILES
CC(C)=CCC\C(C)=C/CCC(C)=O
InChI Identifier
InChI=1S/C13H22O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h7,9H,5-6,8,10H2,1-4H3/b12-9-
InChI KeyHNZUNIKWNYHEJJ-XFXZXTDPSA-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
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.094 g/LALOGPS
logP4.59ALOGPS
logP3.68ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)19.6ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity63.83 m³·mol⁻¹ChemAxon
Polarizability24.21 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9500000000-c7325d4dbb4acd6664adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-22aaf2de71220d323f8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05y1-5900000000-b9793a3c456efd9db543Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9200000000-0ccb71b516f62ccb1982Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-49a606374f47e6c4e143Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2900000000-37d60e4771277898dc21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9600000000-52911be4f91a2692f60aSpectrum
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 IDFDB008529
KNApSAcK IDC00029336
Chemspider ID1362229
KEGG Compound IDC13297
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1713001
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ishihara T, Suemasu S, Asano T, Tanaka K, Mizushima T: Stimulation of gastric ulcer healing by heat shock protein 70. Biochem Pharmacol. 2011 Oct 1;82(7):728-36. doi: 10.1016/j.bcp.2011.06.030. Epub 2011 Jun 28. [PubMed:21736872 ]
  2. Talavera-Bianchi M, Adhikari K, Chambers E 4th, Carey EE, Chambers DH: Relation between developmental stage, sensory properties, and volatile content of organically and conventionally grown pac choi (Brassica rapa var. Mei Qing Choi). J Food Sci. 2010 May;75(4):S173-81. doi: 10.1111/j.1750-3841.2010.01585.x. [PubMed:20546419 ]
  3. Coelho E, Perestrelo R, Neng NR, Camara JS, Coimbra MA, Nogueira JM, Rocha SM: Optimisation of stir bar sorptive extraction and liquid desorption combined with large volume injection-gas chromatography-quadrupole mass spectrometry for the determination of volatile compounds in wines. Anal Chim Acta. 2008 Aug 22;624(1):79-89. doi: 10.1016/j.aca.2008.06.032. Epub 2008 Jun 27. [PubMed:18706312 ]
  4. Luo FC, Zhao L, Deng J, Liang M, Zeng XS, Liu H, Bai J: Geranylgeranylacetone protects against morphine-induced hepatic and renal damage in mice. Mol Med Rep. 2013 Feb;7(2):694-700. doi: 10.3892/mmr.2012.1217. Epub 2012 Dec 3. [PubMed:23229517 ]
  5. Arteaga JF, Domingo V, Quilez del Moral JF, Barrero AF: First total synthesis of (-)-achilleol B: reassignment of its relative stereochemistry. Org Lett. 2008 May 1;10(9):1723-6. doi: 10.1021/ol800326n. Epub 2008 Apr 2. [PubMed:18380440 ]
  6. Haberer W, Schmitt T, Peschke K, Schreier P, Muller JK: Ethyl 4-methyl heptanoate: a male-produced pheromone of Nicrophorus vespilloides. J Chem Ecol. 2008 Jan;34(1):94-8. Epub 2007 Dec 13. [PubMed:18080163 ]
  7. Luo FC, Qi L, Lv T, Wang SD, Liu H, Nakamura H, Yodoi J, Bai J: Geranylgeranylacetone protects mice against morphine-induced hyperlocomotion, rewarding effect, and withdrawal syndrome. Free Radic Biol Med. 2012 Apr 1;52(7):1218-27. doi: 10.1016/j.freeradbiomed.2012.01.004. Epub 2012 Jan 18. [PubMed:22285390 ]
  8. Lennikov A, Kitaichi N, Kase S, Noda K, Horie Y, Nakai A, Ohno S, Ishida S: Induction of heat shock protein 70 ameliorates ultraviolet-induced photokeratitis in mice. Int J Mol Sci. 2013 Jan 22;14(1):2175-89. doi: 10.3390/ijms14012175. [PubMed:23340653 ]
  9. Hoogstra-Berends F, Meijering RA, Zhang D, Heeres A, Loen L, Seerden JP, Kuipers I, Kampinga HH, Henning RH, Brundel BJ: Heat shock protein-inducing compounds as therapeutics to restore proteostasis in atrial fibrillation. Trends Cardiovasc Med. 2012 Apr;22(3):62-8. doi: 10.1016/j.tcm.2012.06.013. Epub 2012 Aug 3. [PubMed:22863365 ]
  10. Ning JW, Lin GB, Ji F, Xu J, Sharify N: Preventive effects of geranylgeranylacetone on rat ethanol-induced gastritis. World J Gastroenterol. 2012 May 14;18(18):2262-9. doi: 10.3748/wjg.v18.i18.2262. [PubMed:22611321 ]
  11. Shimotori Y, Hattori K, Aoyama M, Miyakoshi T: Acyclic monoterpenes in tree essential oils as a shrinking agent for waste-expanded polystyrene. J Environ Sci Health A Tox Hazard Subst Environ Eng. 2011;46(8):813-6. doi: 10.1080/10934529.2011.579842. [PubMed:21644162 ]
  12. Aboaba SA, Ogunwande IA, Walker TM, Setzer WN, Oladosu IA, Ekundayo O: Essential oil composition, antibacterial activity and toxicity of the leaves of Tetrapleura tetraptera (Schum. & Thonn.) taubert from Nigeria. Nat Prod Commun. 2009 Feb;4(2):287-90. [PubMed:19370941 ]
  13. Bruder M, Smith SJ, Blake AJ, Moody CJ: Synthesis of (+/-)-likonide B (smenochromene D) using a regioselective Claisen rearrangement, separation of the enantiomers and stereochemical assignment. Org Biomol Chem. 2009 May 21;7(10):2127-34. doi: 10.1039/b901358j. Epub 2009 Mar 27. [PubMed:19421451 ]
  14. Jumtee K, Komura H, Bamba T, Fukusaki E: Predication of Japanese green tea (Sen-cha) ranking by volatile profiling using gas chromatography mass spectrometry and multivariate analysis. J Biosci Bioeng. 2011 Sep;112(3):252-5. doi: 10.1016/j.jbiosc.2011.05.008. Epub 2011 Jun 12. [PubMed:21664180 ]
  15. Wang N, Min X, Li D, He P, Zhao L: Geranylgeranylacetone protects against myocardial ischemia and reperfusion injury by inhibiting high-mobility group box 1 protein in rats. Mol Med Rep. 2012 Feb;5(2):521-4. doi: 10.3892/mmr.2011.666. Epub 2011 Nov 4. [PubMed:22075975 ]
  16. Hasegawa M, Ishiguro K, Ando T, Goto H: Geranylgeranylacetone attenuates cisplatin-induced reductions in cell viability by suppressing the elevation of intracellular p53 content without heat shock protein induction. Nagoya J Med Sci. 2012 Feb;74(1-2):123-31. [PubMed:22515118 ]
  17. Seifert A, Vomund S, Grohmann K, Kriening S, Urlacher VB, Laschat S, Pleiss J: Rational design of a minimal and highly enriched CYP102A1 mutant library with improved regio-, stereo- and chemoselectivity. Chembiochem. 2009 Mar 23;10(5):853-61. doi: 10.1002/cbic.200800799. [PubMed:19222039 ]
  18. Furstenau B, Rosell G, Guerrero A, Quero C: Electrophysiological and behavioral responses of the black-banded oak borer, Coroebus florentinus, to conspecific and host-plant volatiles. J Chem Ecol. 2012 Apr;38(4):378-88. doi: 10.1007/s10886-012-0110-1. Epub 2012 Apr 4. [PubMed:22477026 ]
  19. Nagano Y, Matsui H, Shimokawa O, Hirayama A, Nakamura Y, Tamura M, Rai K, Kaneko T, Hyodo I: Bisphosphonate-induced gastrointestinal mucosal injury is mediated by mitochondrial superoxide production and lipid peroxidation. J Clin Biochem Nutr. 2012 Nov;51(3):196-203. doi: 10.3164/jcbn.12-41. Epub 2012 Sep 5. [PubMed:23170047 ]
  20. Fonseca MG, Vidal DM, Zarbin PH: Male-produced sex pheromone of the cerambycid beetle Hedypathes betulinus: chemical identification and biological activity. J Chem Ecol. 2010 Oct;36(10):1132-9. doi: 10.1007/s10886-010-9850-y. Epub 2010 Aug 31. [PubMed:20809143 ]
  21. Hughes DT, Pelletier J, Luetje CW, Leal WS: Odorant receptor from the southern house mosquito narrowly tuned to the oviposition attractant skatole. J Chem Ecol. 2010 Aug;36(8):797-800. doi: 10.1007/s10886-010-9828-9. Epub 2010 Jul 11. [PubMed:20623327 ]
  22. Gao H, Zhu H, Shao Y, Chen A, Lu C, Zhu B, Luo Y: Lycopene accumulation affects the biosynthesis of some carotenoid-related volatiles independent of ethylene in tomato. J Integr Plant Biol. 2008 Aug;50(8):991-6. doi: 10.1111/j.1744-7909.2008.00685.x. [PubMed:18713349 ]
  23. Namba T, Tanaka K, Hoshino T, Azuma A, Mizushima T: Suppression of expression of heat shock protein 70 by gefitinib and its contribution to pulmonary fibrosis. PLoS One. 2011;6(11):e27296. doi: 10.1371/journal.pone.0027296. Epub 2011 Nov 9. [PubMed:22096546 ]
  24. Isoir M, Roque T, Squiban C, Milliat F, Mondon P, Mas-Chamberlin C, Benderitter M, Guipaud O, Tamarat R: Protective effect of geranylgeranylacetone against radiation-induced delayed effects on human keratinocytes. Radiat Res. 2013 Feb;179(2):232-42. doi: 10.1667/RR2717.1. Epub 2013 Jan 4. [PubMed:23289389 ]
  25. Logan JG, Seal NJ, Cook JI, Stanczyk NM, Birkett MA, Clark SJ, Gezan SA, Wadhams LJ, Pickett JA, Mordue AJ: Identification of human-derived volatile chemicals that interfere with attraction of the Scottish biting midge and their potential use as repellents. J Med Entomol. 2009 Mar;46(2):208-19. [PubMed:19351071 ]
  26. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  27. 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 ]
  28. 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 ]
  29. 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 ]
  30. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  31. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.