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 |
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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 | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-014i-9300000000-1ee3bddd85e9086b7517 | 2015-03-01 | View Spectrum | Predicted GC-MS | Geranylgeraniol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0aor-6590000000-d53875d1d1717d638752 | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-006y-0290000000-406439b04dab8ae9f72a | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0603-4970000000-f76480cde6f70f69904f | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0lk9-9730000000-6885c45bb706a217604b | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-ae922ee5b3568def3a2b | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4r-0090000000-bd08abbb2b7066c4796a | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0596-3590000000-59768ae8b64336ff3df0 | 2016-08-03 | View Spectrum |
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NMR | |
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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 | Descriptor | ID | Definition | Reference |
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Anti adenomic | 35610 | An agent that inhibits adenoma growth, reducing tumor formation. It plays a biological role in regulating cell proliferation and differentiation. Therapeutically, it is used to prevent or treat adenoma-related disorders, with key medical applications in managing conditions such as colon polyps, pituitary adenomas, and other glandular tumors. | DUKE | Anti-cancer | 35610 | An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival. | DUKE | Anti carcinomic | 35610 | An agent that inhibits the growth and proliferation of cancer cells, playing a crucial role in cancer prevention and treatment. Therapeutically, it is used to manage and treat various types of cancer, reducing tumor size and slowing disease progression, with key medical uses in oncology and chemotherapy. | DUKE | Anti leukemic | 35610 | An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies. | DUKE | Anti proliferant | | An agent that prevents or inhibits cell growth and division, used therapeutically to treat cancer, manage tumor growth, and prevent restenosis after angioplasty, reducing abnormal cell proliferation. | DUKE | Apoptotic | | An agent that stimulates programmed cell death, playing a crucial biological role in eliminating damaged or unwanted cells. It has therapeutic applications in cancer treatment, and key medical uses include inducing cell death in malignant cells, reducing tumor growth, and enhancing chemotherapy efficacy. | DUKE | Cancer preventive | 35610 | An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence. | DUKE | Pesticide | 25944 | An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections. | DUKE | Protisticide | | An agent that kills protozoans, used as a herbicide or in therapeutic applications to treat protozoan infections, with key medical uses including managing parasitic diseases and infections. | DUKE | Schistosomicide | | An agent destructive to schistosomes, used to treat schistosomiasis, a disease caused by blood flukes transmitted by snails. Therapeutically, it eliminates the parasites, reducing inflammation and preventing long-term damage. Key medical uses include treating and preventing schistosomiasis in endemic regions, particularly in Africa, Brazil, and Asia. | DUKE |
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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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