1-(3-hexanoyl-2,4,6-trihydroxyphenyl)hexan-1-one

• ChemBase ID: 154668
• Molecular Formular: C18H26O5
• Molecular Mass: 322.39604
• Monoisotopic Mass: 322.17802393
• SMILES: CCCCCC(=O)c1c(cc(c(c1O)C(=O)CCCCC)O)O
• Canonical SMILES: CCCCCC(=O)c1c(O)cc(c(c1O)C(=O)CCCCC)O
• InChI: InChI=1S/C18H26O5/c1-3-5-7-9-12(19)16-14(21)11-15(22)17(18(16)23)13(20)10-8-6-4-2/h11,21-23H,3-10H2,1-2H3
• InChIKey: JRHOSBCIYWDGHN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(3-hexanoyl-2,4,6-trihydroxyphenyl)hexan-1-one
• IUPAC Traditional name: 1-(3-hexanoyl-2,4,6-trihydroxyphenyl)hexan-1-one
• Synonyms: 1,1′-(2,4,6-Trihydroxy-1,3-phenylene)bis-1-hexanone; 2,4-(bis-1-ketohexyl)phloroglucinol; Hyp9

Database IDs

• CAS Number: 3118-34-1
• MDL Number: MFCD16875422
• PubChem SID: 162248806
• PubChem CID: 15659415

CALCULATED PROPERTIES

• Acid pKa: 8.420199
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 6.8458114
• LogD (pH = 7.4): 6.8068833
• Log P: 6.8463287
• Molar Refractivity: 89.6661 cm^3
• Polarizability: 34.36583 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: white to light yellow powder

Safety Information

• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C18H26O5

DETAILS

Sigma Aldrich - H9791

Biochem/physiol Actions
Hyperforin is the active ingredient in St. John′s Wort. It is used to treat depression, known to indirectly inhibit reuptake of serotonin and norepinephrine at the synapse, and recently discovered to exert its actions by directly activating TRPC6. TRPC6 is a member of the canonical transient receptor potential (TRPC) family of ion channels. DAG is the endogenous activator of this channel, and Hyperforin is the only known TRPC6-selective activator. Although it is broadly used, Hyperforin is chemically unstable. Efforts to find a stable but pharmacologically similar TRPC6 activator resulted in the discovery of Hyp9, a simplified phloroglucinol derivative. Like Hyperforin, Hyp9 inhibits serotonin reuptake and induces neurite outgrowth. It increases calcium entry into the cell and selectively increases current through TRPC6 channels.