3-HYDROXYDECANOIC ACID

3-HYDROXYDECANOIC ACID Property

Melting point:

47-48 °C

Boiling point:

318.2±25.0 °C(Predicted)

Density 

1.011±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

4.39±0.10(Predicted)

color 

White to Off-White

InChI

InChI=1S/C10H20O3/c1-2-3-4-5-6-7-9(11)8-10(12)13/h9,11H,2-8H2,1H3,(H,12,13)

InChIKey

FYSSBMZUBSBFJL-UHFFFAOYSA-N

SMILES

OC(=O)CC(O)CCCCCCC

LogP

2.293 (est)

Safety

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

3-HYDROXYDECANOIC ACID Chemical Properties,Usage,Production

Description

3-hydroxy Decanoic acid is a hydroxy fatty acid and the predominant monomer in methyl-branched poly(3-hydroxyalkanoate) (PHA) polymers produced by P. putida CA-3. It is present in LPS from the H. pylori strain SS1 and in the lipid A component of clinical isolates of P. aeruginosa isolated from patients with cystic fibrosis but not the environment or patients with other conditions. 3-hydroxy Decanoic acid inhibits mitotic progression of O. virens pollens via impairment of plasma membrane function. It also induces a reversible shape change of the membrane crenation in human erythrocytes. [Matreya, LLC. Catalog No. 1727]

Uses

3-Hydroxycapric acid is an inhibitor for mitotic progression.

Definition

ChEBI: A medium-chain fatty acid that is decanoic acid substituted at position 3 by a hydroxy group.

Synthesis

Preparation of 3-hydroxydecanoic acid: 16.5 g (50 mmol) of ethyl 3-hydroxydecanoate prepared by process (1) was co-dissolved with 10.0 g (250 mmol) of lithium hydroxide in 50 mL of a solvent mixture consisting of tetrahydrofuran and water (1:2, v/v). The reaction mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, the reaction solution was neutralized with dilute hydrochloric acid and subsequently concentrated under reduced pressure. The concentrated residue was extracted with ethyl acetate. The ethyl acetate layer obtained from the extraction was sequentially washed with saturated brine and dried with anhydrous magnesium sulfate, followed by concentration under reduced pressure to remove the solvent. The concentrated residue was purified by silica gel column chromatography (eluent: ethyl acetate/methanol=4/6, v/v) to obtain the target product 3-hydroxydecanoic acid in 90% yield. Yield: 12.2 g (45 mmol). The product was characterized by 1H-NMR (CDCl3,500MHz): δ 0.86 (t, 3H), 1.25 (m, 14H), 1.33 (m, 2H), 2.31 (m, 2H), 3.79 (m, 1H).

IC 50

Human Endogenous Metabolite

References

[1] Iwanami Y. et al. Myrmicacin, a new inhibitor for mitotic progression after metaphase. Protoplasma. 1978;95(3):267-71. DOI:10.1007/BF01294455