Record Information
Version1.0
Creation date2010-04-08 22:05:00 UTC
Update date2019-11-26 02:56:34 UTC
Primary IDFDB001528
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGeranylgeraniol
DescriptionGeranylgeraniol, 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 .
CAS Number24034-73-9
Structure
Thumb
Synonyms
SynonymSource
(2E,6E,10E)-GeranylgeraniolChEBI
Geranylgeraniol, (e,e,e)-isomerMeSH
Geranylgeraniol, (Z,Z,Z)-isomerMeSH
TetraprenolMeSH
(2E,6E,10E)-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-olPhytoBank
(E,E,E)-GeranylgeraniolPhytoBank
(E,E,E)-Geranylgeranyl alcoholPhytoBank
All-trans-GeranylgeraniolPhytoBank
GeranylgeraniolPhytoBank
Geranylgeranyl alcoholPhytoBank
trans,trans,trans-GeranylgeraniolPhytoBank
trans-GeranylgeraniolPhytoBank
(e,e,e)-geranylgeraniolbiospider
2,6,10,14-hexadecatetraen-1-ol, 3,7,11,15-tetramethyl-biospider
All-trans-geranylgeraniolbiospider
Gernaylgeraniolbiospider
Trans-geranylgeraniolbiospider
Trans,trans,trans-geranylgeraniolbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.0054 g/LALOGPS
logP6.06ALOGPS
logP5.82ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)16.33ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity98.79 m³·mol⁻¹ChemAxon
Polarizability38.18 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H34O
IUPAC name(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol
InChI IdentifierInChI=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+
InChI KeyOJISWRZIEWCUBN-QIRCYJPOSA-N
Isomeric SMILES[H]\C(CO)=C(\C)CC\C([H])=C(/C)CC\C([H])=C(/C)CCC=C(C)C
Average Molecular Weight290.4834
Monoisotopic Molecular Weight290.26096571
Classification
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentAcyclic diterpenoids
Alternative Parents
Substituents
  • Acyclic diterpenoid
  • Long chain fatty alcohol
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-014i-9300000000-1ee3bddd85e9086b75172015-03-01View Spectrum
Predicted GC-MSGeranylgeraniol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0aor-6590000000-d53875d1d1717d638752Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006y-0290000000-406439b04dab8ae9f72a2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0603-4970000000-f76480cde6f70f69904f2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lk9-9730000000-6885c45bb706a217604b2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-ae922ee5b3568def3a2b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0090000000-bd08abbb2b7066c4796a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-3590000000-59768ae8b64336ff3df02016-08-03View Spectrum
NMR
TypeDescriptionView
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09094
Pubchem Compound ID5281365
Pubchem Substance IDNot Available
ChEBI ID46762
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDGERANYL-GERANIOL
BIGG IDNot Available
KNApSAcK IDC00003428
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti adenomic35610 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-cancer35610 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 carcinomic35610 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 leukemic35610 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 proliferantAn 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
ApoptoticAn 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 preventive35610 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
Pesticide25944 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
ProtisticideAn 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
SchistosomicideAn 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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
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.