(2Z)-dodec-2-enoic acid

• ChemBase ID: 154301
• Molecular Formular: C12H22O2
• Molecular Mass: 198.30188
• Monoisotopic Mass: 198.16197994
• SMILES: CCCCCCCCC/C=C\C(=O)O
• Canonical SMILES: CCCCCCCCC/C=C\C(=O)O
• InChI: InChI=1S/C12H22O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h10-11H,2-9H2,1H3,(H,13,14)/b11-10-
• InChIKey: PAWGRNGPMLVJQH-KHPPLWFESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-dodec-2-enoic acid
• IUPAC Traditional name: BDSF
• Synonyms: BDSF; Burkholderia cenocepacia diffusible signal factor; cis-2-Dodecenoic acid

Database IDs

• CAS Number: 55928-65-9
• MDL Number: MFCD16661220
• Beilstein Number: 1722818
• PubChem SID: 162248440
• PubChem CID: 5312376

CALCULATED PROPERTIES

• Acid pKa: 5.0255046
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.876422
• LogD (pH = 7.4): 2.1291854
• Log P: 4.4761314
• Molar Refractivity: 59.7729 cm^3
• Polarizability: 23.099695 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 41-51/53
• Safety Statements: 26-39-61
• GHS Pictograms: GHS05; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H318-H411
• GHS Precautionary statements: P273-P280-P305 + P351 + P338
• Storage Temperature: -20°C

Product Information

• Purity: ≥95.0% (HPLC)
• Empirical Formula (Hill Notation): C12H22O2

DETAILS

Sigma Aldrich - 49619

Biochem/physiol Actions
Burkholderia cenocepacia produces a diffusible fatty acid signal molecule, cis-2-dodecenoic acid (BDSF), that has been implicated in interspecies and interkingdom communication1.