(2S)-1-hydroxy-3-(octanoyloxy)propan-2-yl octanoate

• ChemBase ID: 131596
• Molecular Formular: C19H36O5
• Molecular Mass: 344.48614
• Monoisotopic Mass: 344.25627425
• SMILES: CCCCCCCC(=O)OC[C@H](CO)OC(=O)CCCCCCC
• Canonical SMILES: CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC)CO
• InChI: InChI=1S/C19H36O5/c1-3-5-7-9-11-13-18(21)23-16-17(15-20)24-19(22)14-12-10-8-6-4-2/h17,20H,3-16H2,1-2H3/t17-/m0/s1
• InChIKey: ZQBULZYTDGUSSK-KRWDZBQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-hydroxy-3-(octanoyloxy)propan-2-yl octanoate
• IUPAC Traditional name: (2S)-1-hydroxy-3-(octanoyloxy)propan-2-yl octanoate
• Synonyms: (S)-Glycerol 1,2-dioctanoate; 1,2-Dicapryloyl-sn-glycerol; D-α,β-Dicaprylin; DOG; 1,2-Dioctanoyl-sn-glycerol

Database IDs

• CAS Number: 60514-48-9
• MDL Number: MFCD00036835
• Beilstein Number: 1714754
• PubChem SID: 24893929; 162225874
• PubChem CID: 148879

CALCULATED PROPERTIES

• Acid pKa: 14.577784
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.889995
• LogD (pH = 7.4): 4.889995
• Log P: 4.889995
• Molar Refractivity: 94.0829 cm^3
• Polarizability: 37.883293 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble
• Apperance: yellow oil

Safety Information

• RTECS: RH0764500
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: -20°C

Product Information

• Purity: ≥96% (TLC)
• Shipped in: dry ice

DETAILS

Sigma Aldrich - D5156

Caution
Some isomerization to the 1,3-isomer may occur in storage or in solution.
Other Notes
Synthetic 1,2-diglyceride of short chain fatty acid.
Biochem/physiol Actions
Cell-permeable, diacylglycerol (DAG) analog, and activator of protein kinase C (PKC). Shown to possess a lower affinity for the α isoform of PKC than for the other isoforms. Mimics the action of tumor-promoting phorbol esters, such as phorbol 12-myristate 13-acetate (PMA). Inhibits slow (L-type) Ca2+ current in rat heart cells independently of PKC activation and also inhibits the cGMP-gated channel in rod outer segments by a phosphorylation-independent mechanism.