[({[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid

• ChemBase ID: 127547
• Molecular Formular: C10H20O7P2
• Molecular Mass: 314.209122
• Monoisotopic Mass: 314.06842624
• SMILES: O=P(O)(O)OP(=O)(OC/C=C(/CCC=C(C)C)\C)O
• Canonical SMILES: C/C(=C\COP(=O)(OP(=O)(O)O)O)/CCC=C(C)C
• InChI: InChI=1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)
• InChIKey: GVVPGTZRZFNKDS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [({[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid; ({[(3,7-dimethylocta-2,6-dien-1-yl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
• IUPAC Traditional name: geranyl diphosphate; [(3,7-dimethylocta-2,6-dien-1-yl)oxy(hydroxy)phosphoryl]oxyphosphonic acid
• Synonyms: trans-3,7-Dimethyl-2,6-octadienyl pyrophosphate; GPP; Geranyl pyrophosphate ammonium salt; Geranyl pyrophosphate

Database IDs

• CAS Number: 763-10-0
• MDL Number: MFCD00189726
• PubChem SID: 24895272; 162221866
• PubChem CID: 445995
• CHEBI ID: 17211
• CHEMBL: 41342
• Chemspider ID: 393471
• DrugBank ID: DB02552
• MeSH Name: Geranyl+pyrophosphate
• Wikipedia Title: Geranyl_pyrophosphate

CALCULATED PROPERTIES

• Acid pKa: 1.7672187
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.449496
• LogD (pH = 7.4): -3.0771651
• Log P: 1.9570187
• Molar Refractivity: 72.9279 cm^3
• Polarizability: 28.213772 Å^3
• Polar Surface Area: 113.29 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 20 °C; 68 °F

Safety Information

• European Hazard Symbols: Flammable (F); Toxic (T)
• German water hazard class: 1
• Risk Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 16-36/37-45
• GHS Pictograms: GHS02; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H301-H311-H331-H370
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (TLC)
• Concentration: 1 mg/mL in methanol (:aqueous 10 mM NH4OH (7:3))
• Packaging: vial of 200 μg

DETAILS

Sigma Aldrich - G6772

Biochem/physiol Actions
Intermediate in terpene biosynthesis
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. G6772.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.