(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol

• ChemBase ID: 106058
• Molecular Formular: C20H34O
• Molecular Mass: 290.48336
• Monoisotopic Mass: 290.26096571
• SMILES: CC(=CCC/C(=C/CC/C(=C/CC/C(=C/CO)/C)/C)/C)C
• Canonical SMILES: OC/C=C(/CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)\C
• InChI: 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
• InChIKey: OJISWRZIEWCUBN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol; 3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol
• IUPAC Traditional name: geranylgeraniol; tetraprenol
• Synonyms: (2E,6E,10E)-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-ol; (E,E,E)- 3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-ol; (E,E,E)-Geranylgeraniol; All-trans-Geranylgeraniol; trans,trans,trans-Geranylgeraniol; trans-Geranylgeraniol; Tetraprenol; all trans-3,7,11-15-Tetramethyl-2,6,10,14-hexadecatetraen-1-ol; Geranylgeraniol; GERANYLGERANIOL

Database IDs

• CAS Number: 24034-73-9
• MDL Number: MFCD00129083
• Beilstein Number: 1913779
• PubChem SID: 24895120; 162093886
• PubChem CID: 5281365
• Chemspider ID: 4444726
• Wikipedia Title: Geranylgeraniol

CALCULATED PROPERTIES

• Acid pKa: 16.330025
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 5.8218117
• LogD (pH = 7.4): 5.8218117
• Log P: 5.8218117
• Molar Refractivity: 98.7873 cm^3
• Polarizability: 37.32096 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Hexane
• Apperance: Clear liquid; Light Yellow Oil; liquid
• Density: 0.88 g/ml

Safety Information

• Storage Condition: 0°C; -86°C Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥85% (GC)

DETAILS

MP Biomedicals - 02198770

Clear, colorless liquid.
Useful for studying mammalian cell protein isoprenylation.
May affect regulation of cell cycle progress.

Sigma Aldrich - G3278

Biochem/physiol Actions
As the pyrophosphate, the metabolic precursor of all diterpenes. Screening in vitro shows this to be a potent and selective agent against Mycobacterium tuberculosis.1

Toronto Research Chemicals - G367500

Geranylgeraniol, a precursor to Geranylgeranylpyrophosphate (G367600), is an intermediate in the mevalonate pathway. Geranylgeraniol has been shown to prevent bone re-adsorption, inhibition of osteoclast formation, and kinase activation in vitro.

REFERENCES

• Crick, et al. Biochemical and Biophysical Research Commun. , 237 : 483.
• Aiuchi, T., et al.: J. Biochem., 124, 300 (1998)
• Fisher, J.E., et al.: Proc. Natl. Acad. Sci. U.S.A. 96, 133 (1998)
• Montero, M.T., et al.: J. Immunol., 173, 4936 (1998)
• Campia, I., et al.: Br. J. Pharmacol., 158, 1777 (1998)