2-hydroxytetradecanoic acid

• ChemBase ID: 105373
• Molecular Formular: C14H28O3
• Molecular Mass: 244.37032
• Monoisotopic Mass: 244.20384476
• SMILES: CCCCCCCCCCCCC(O)C(=O)O
• Canonical SMILES: CCCCCCCCCCCCC(C(=O)O)O
• InChI: InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-12-13(15)14(16)17/h13,15H,2-12H2,1H3,(H,16,17)
• InChIKey: JYZJYKOZGGEXSX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxytetradecanoic acid
• IUPAC Traditional name: 2-hydroxymyristic acid; α-hydroxymyristate
• Synonyms: α-HYDROXY-n-TETRADECYLIC ACID; 2-Hydroxy-tetradecanoic Acid; (+/-)-α-Hydroxymyristic Acid; NSC 18938; D,L-α-Hydroxy Myristic Acid; 2-Hydroxymyristic acid; DL-α-Hydroxymyristic acid; 2-Hydroxytetradecanoic acid; DL-α-Hydroxymyristic acid; 2-Hydroxytetradecanoic acid; 2-HYDROXYMYRISTIC ACID

Database IDs

• CAS Number: 2507-55-3
• EC Number: 219-714-0
• MDL Number: MFCD00014342
• Beilstein Number: 1725369
• PubChem SID: 162092630; 24895765
• PubChem CID: 1563

CALCULATED PROPERTIES

• Acid pKa: 4.2555575
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.2301264
• LogD (pH = 7.4): 1.5014831
• Log P: 4.4963794
• Molar Refractivity: 69.3738 cm^3
• Polarizability: 27.644499 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: soluble4 mg/mL (with heating in a 70°C water bath); H2O: soluble5 mg/mL
• Apperance: Off-White Solid; white
• Melting Point: 70-72°C

Safety Information

• Storage Condition: 0°C; -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (capillary GC); 98%

DETAILS

MP Biomedicals - 02159939

Purity: 98%
A posttranslational modification reagent which inhibits protein myristoylation after metabolic activation. A useful tool for differentiating myristoylation and palmitoylation of proteins. It prevents p56 mediated signal transduction and stops Varicella zoster virus replication.

MP Biomedicals - 05221025

MP Biomedicals Rare Chemical collection

Sigma Aldrich - H6771

Biochem/physiol Actions
An analog of myristic acid that becomes metabolically activated in cells to form 2-hydroxymyristoyl-CoA. Inhibitor of protein myristoylation.

Toronto Research Chemicals - H948500

A biological fatty Acid, used in cosmetics, skin treatments, and hair preparations.

REFERENCES

• Abraham, N. and Veillette, A., Mol. Cell. Bio. , 10 : 5197, (1990).
• Spiegel, A.M., et al., Trends Biochem. Sci. , 16 : 338, (1991).
• Paige, L.A., et al., J. Biol. Chem. , 268 : 8669, (1993).
• Boisson, B., et al.: Anal. Biochem., 322, 116 (2003)
• Inglis, T., et al.: J. Clin. Microbiol., 41, 4812 (2003)
• Bohn, M., et al.: J. Plant Physiol., 164, 146 (2003)