dodec-2-enedioic acid

• ChemBase ID: 102799
• Molecular Formular: C12H20O4
• Molecular Mass: 228.2848
• Monoisotopic Mass: 228.13615912
• SMILES: OC(=O)CCCCCCCC/C=C/C(=O)O
• Canonical SMILES: OC(=O)CCCCCCCC/C=C/C(=O)O
• InChI: InChI=1S/C12H20O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h7,9H,1-6,8,10H2,(H,13,14)(H,15,16)
• InChIKey: MAZWDMBCPDUFDJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dodec-2-enedioic acid; (2E)-dodec-2-enedioic acid
• IUPAC Traditional name: 2-dodecenedioic acid; traumatic acid
• Synonyms: 2-Dodecenedioic acid; TRAUMATIC ACID; trans-2-Dodecenedioic acid; Traumatic acid; trans-Traumatic acid; Traumatic acid; trans-2-Dodecenedioic acid; trans-Traumatic acid

Database IDs

• CAS Number: 6402-36-4
• EC Number: 229-019-4
• MDL Number: MFCD00004443
• Beilstein Number: 1725762
• PubChem SID: 24850624; 24889328; 162090581; 24893951
• PubChem CID: 5283028
• CHEMBL: 470062
• Wikipedia Title: Traumatic_acid

CALCULATED PROPERTIES

• Molar Refractivity: 61.4383 cm^3
• Polarizability: 23.648703 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true
• Acid pKa: 4.7222753
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.9531844
• LogD (pH = 7.4): -1.5420831
• Log P: 3.1558897

PROPERTIES

Physical Property

• Solubility: Sparingly soluble in water
• Melting Point: 164-166 °C; 165-167 °C(lit.); 166-167 °C
• Boiling Point: 150-160 °C at 0.001 mmHg

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

Product Information

• Purity: ≥98.0% (T); 97%
• Grade: for prostaglandin synthesis; purum
• Linear Formula: HO2C(CH2)8CH=CHCO2H
• Empirical Formula (Hill Notation): C12H20O4

DETAILS

MP Biomedicals - 05208899

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02103096

Trans Isomer
Crystalline

Sigma Aldrich - 177245

Biochem/physiol Actions
Traumatic acid (1 uM) incubated for 30 minutes with sprouts of 9- to 11-day-old seedlings of pea increases total tyrosine phosphorylation of pea proteins 1. The effect of traumatic acid has differential effects, with an increase in tyrosine phosphorylation in some proteins, but with a decrease in others.