2-(12-hydroxydodeca-5,10-diyn-1-yl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione

• ChemBase ID: 105205
• Molecular Formular: C21H26O3
• Molecular Mass: 326.42934
• Monoisotopic Mass: 326.18819469
• SMILES: CC1=C(C)C(=O)C(=C(C)C1=O)CCCCC#CCCCC#CCO
• Canonical SMILES: OCC#CCCCC#CCCCCC1=C(C)C(=O)C(=C(C1=O)C)C
• InChI: InChI=1S/C21H26O3/c1-16-17(2)21(24)19(18(3)20(16)23)14-12-10-8-6-4-5-7-9-11-13-15-22/h22H,5,7-10,12,14-15H2,1-3H3
• InChIKey: WDEABJKSGGRCQA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(12-hydroxydodeca-5,10-diyn-1-yl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione
• IUPAC Traditional name: docebenone
• Synonyms: AA-861; 2-(12-Hydroxydodeca-5,10-divinyl)-3,5,6-trimethyl-1,4-benzoquinone; 2-(12-Hydroxydodeca-5,10-diynyl)-3,5,6-trimethyl-p-benzoquinone; AA-861

Database IDs

• CAS Number: 80809-81-0
• MDL Number: MFCD00210243
• PubChem SID: 162092139; 24278214
• PubChem CID: 1967

CALCULATED PROPERTIES

• Acid pKa: 13.552656
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 5.3852134
• LogD (pH = 7.4): 5.385213
• Log P: 5.3852134
• Molar Refractivity: 99.5657 cm^3
• Polarizability: 36.764736 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: ethanol: soluble
• Melting Point: 56-59°C

Safety Information

• Storage Condition: 2-8°C
• 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: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ALOX5(240)rat ... Alox5(25290)

Product Information

• Purity: ≥98% (HPLC); 95%

DETAILS

MP Biomedicals - 02159061

Purity: 95%
Orally active, specific and potent inhibitor of 5-lipoxygenase.

Sigma Aldrich - A3711

Biochem/physiol Actions
5-Lipoxygenase inhibitor.

REFERENCES

• Yoshimoto, T., et al., Biochem. Biophys. Acta , 713 : 470, (1982).
• Ashida, Y., et al., Prostaglandins , 26 : 955, (1983).
• Ancill, R.J., et al., J. Int. Med. Res. , 18 : 75, (1990).