6,10,14,18-tetramethylnonadeca-5,9,13,17-tetraen-2-one

• ChemBase ID: 154595
• Molecular Formular: C23H38O
• Molecular Mass: 330.54722
• Monoisotopic Mass: 330.29226584
• SMILES: CC(=CCC/C(=C/CC/C(=C/CC/C(=C/CCC(=O)C)/C)/C)/C)C
• Canonical SMILES: C/C(=C\CC/C(=C/CCC(=O)C)/C)/CC/C=C(/CCC=C(C)C)\C
• InChI: InChI=1S/C23H38O/c1-19(2)11-7-12-20(3)13-8-14-21(4)15-9-16-22(5)17-10-18-23(6)24/h11,13,15,17H,7-10,12,14,16,18H2,1-6H3
• InChIKey: HUCXKZBETONXFO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6,10,14,18-tetramethylnonadeca-5,9,13,17-tetraen-2-one; (5E,9E,13E)-6,10,14,18-tetramethylnonadeca-5,9,13,17-tetraen-2-one
• IUPAC Traditional name: 6,10,14,18-tetramethylnonadeca-5,9,13,17-tetraen-2-one; teprenone
• Synonyms: 6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetraen-2-one, mixture of (5E,9E,13E) and (5Z,9E,13E) isomers; GGA; Selbex; Teprenone; UNII-S8S8451A4O; Geranylgeranylacetone; 6,10,14,18-Tetramethyl-5,9,13,17-nonadecatetraen-2-one; E 0671; E 36U31; Geranylgeranylacetone; all-trans-Teprenone; Teprenone

Database IDs

• CAS Number: 6809-52-5
• MDL Number: MFCD00869547
• PubChem SID: 162248733
• PubChem CID: 5282199

CALCULATED PROPERTIES

• Acid pKa: 19.598763
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 7.001104
• LogD (pH = 7.4): 7.001104
• Log P: 7.001104
• Molar Refractivity: 111.4311 cm^3
• Polarizability: 42.309162 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >5 mg/mL
• Apperance: clear liquid

Safety Information

• Storage Condition: protect from light
• RTECS: RA5391300
• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C23H38O

DETAILS

Sigma Aldrich - G5048

Biochem/physiol Actions
Geranylgeranylacetone can induce expression of HSP70, HSPB8, and HSPB1. Induction of HSP70 expression is protective against the development of various diseases, such as inflammatory bowel disease, hypoxic/ischemic brain injury and spinal and bulbar muscular atrophy (cytoprotective and anti-inflammatory effects). Reports indicate that GGA protects against NSAID-induced gastric and intestinal lesions by induction of HSP70 expression. Other studies have shown that GGA induces expression of HSPB8 and HSPB1 and reduces the formation of amyloid oligomers as well as insoluble aggregates in HSPB5 R120G TG mice.

Toronto Research Chemicals - T103500

An anti-ulcerative. Geranylgeranylacetone can induce expression of HSP70, HSPB8, and HSPB1. Induction of HSP70 expression is protective against the development of various diseases, such as inflammatory bowel disease, hypoxic/ischemic brain injury and spin

REFERENCES

• Murakami, M., et al.: Arzneim.-Forsch., 31, 799 (1981)
• Nishizawa, Y., et al.: Xenobiotica, 17, 575 (1981)