Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:00 UTC |
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Update date | 2019-11-26 02:56:34 UTC |
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Primary ID | FDB001528 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Geranylgeraniol |
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Description | Geranylgeraniol, also known as tetraprenol or (2e,6e,10e)-geranylgeraniol, is a member of the class of compounds known as acyclic diterpenoids. Acyclic diterpenoids are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Thus, geranylgeraniol is considered to be an isoprenoid lipid molecule. Geranylgeraniol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Geranylgeraniol can be found in flaxseed, which makes geranylgeraniol a potential biomarker for the consumption of this food product. Geranylgeraniol is a diterpene alcohol which plays a role in several important biological processes. It is an intermediate in the biosynthesis of other diterpenes and of vitamins E and K. It also used in the post-translational modification known as geranylgeranylation. Geranylgeraniol is a pheromone for bumblebees and a variety of other insects . |
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CAS Number | 24034-73-9 |
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Structure | |
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Synonyms | Synonym | Source |
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(2E,6E,10E)-Geranylgeraniol | ChEBI | Geranylgeraniol, (e,e,e)-isomer | MeSH | Geranylgeraniol, (Z,Z,Z)-isomer | MeSH | Tetraprenol | MeSH | (2E,6E,10E)-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-ol | PhytoBank | (E,E,E)-Geranylgeraniol | PhytoBank | (E,E,E)-Geranylgeranyl alcohol | PhytoBank | All-trans-Geranylgeraniol | PhytoBank | Geranylgeraniol | PhytoBank | Geranylgeranyl alcohol | PhytoBank | trans,trans,trans-Geranylgeraniol | PhytoBank | trans-Geranylgeraniol | PhytoBank | (e,e,e)-geranylgeraniol | biospider | 2,6,10,14-hexadecatetraen-1-ol, 3,7,11,15-tetramethyl- | biospider | All-trans-geranylgeraniol | biospider | Gernaylgeraniol | biospider | Trans-geranylgeraniol | biospider | Trans,trans,trans-geranylgeraniol | biospider |
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Predicted Properties | |
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Chemical Formula | C20H34O |
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IUPAC name | (2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol |
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InChI Identifier | InChI=1S/C20H34O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h9,11,13,15,21H,6-8,10,12,14,16H2,1-5H3/b18-11+,19-13+,20-15+ |
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InChI Key | OJISWRZIEWCUBN-QIRCYJPOSA-N |
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Isomeric SMILES | [H]\C(CO)=C(\C)CC\C([H])=C(/C)CC\C([H])=C(/C)CCC=C(C)C |
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Average Molecular Weight | 290.4834 |
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Monoisotopic Molecular Weight | 290.26096571 |
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Classification |
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Description | belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Diterpenoids |
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Direct Parent | Acyclic diterpenoids |
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Alternative Parents | |
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Substituents | - Acyclic diterpenoid
- Long chain fatty alcohol
- Fatty alcohol
- Fatty acyl
- Organic oxygen compound
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0aor-6590000000-d53875d1d1717d638752 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-006y-0290000000-406439b04dab8ae9f72a | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0603-4970000000-f76480cde6f70f69904f | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0lk9-9730000000-6885c45bb706a217604b | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-ae922ee5b3568def3a2b | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4r-0090000000-bd08abbb2b7066c4796a | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0596-3590000000-59768ae8b64336ff3df0 | JSpectraViewer | MS | Mass Spectrum (Electron Ionization) | splash10-014i-9300000000-1ee3bddd85e9086b7517 | JSpectraViewer | MoNA |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C09094 |
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Pubchem Compound ID | 5281365 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 46762 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | GERANYL-GERANIOL |
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BIGG ID | Not Available |
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KNApSAcK ID | C00003428 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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