Description
10-Hydroxy-2-decenoic acid is a milky white or light yellow, slightly sweet and slightly sour viscous liquid secreted by the nutrient glands on the head of worker bees. value.
Chemical Properties
A white crystal with a melting point of 58-59 ℃, stable in nature, easily soluble in methanol, ethanol, chloroform and ether, slightly soluble in acetone, insoluble in water, acidic to litmus paper, and able to make bromine water Rapid fading can also make potassium permanganate solution fade, but it does not show purple red to ferric chloride.
Uses
As a substance with a variety of physiological activities, 10-Hydroxy-2-decenoic acid is often used to measure the quality of royal jelly, and is also widely used in health food and beverages. Improve the body's immune function and the ability to resist radiation damage.
Definition
ChEBI: (E)-10-hydroxydec-2-enoic acid is an omega-hydroxy amino acid that is 2-decenoic acid in which one of the hydrogens attached to the terminal carbon is replaced by a hydroxy group and in which the C=C double bond has E configuration. It is a component of royal jelly. It has a role as an animal metabolite and a geroprotector. It is an alpha,beta-unsaturated monocarboxylic acid, a straight-chain fatty acid, a hydroxy monounsaturated fatty acid and an omega-hydroxy-medium-chain fatty acid.
Synthesis
4. Saponification reaction
Dissolve 0.60 g (2.81 mmol) of the hydroxy ester obtained in the previous step in 10 volumes of tetrahydrofuran. 3.4 mL (6.75 mmol) of 2 M sodium hydroxide solution was added slowly. The reaction mixture was heated to 65 °C and kept at this temperature for 3 hours. Upon completion of the reaction, the pH of the reaction mixture was adjusted to 2 by dropwise addition of 3 M hydrochloric acid solution. the mixture was concentrated and dried, followed by extraction of the aqueous phase with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 0.6 g of crude product. Purification by recrystallization from cold acetonitrile afforded the target product 10-hydroxy-2-decenoic acid as a white solid in 71% yield (0.37 g).
Characterization data:
TLC: Rf = 0.1 (unfolding agent: heptane/ethyl acetate, 6:4, v/v)
1H NMR (300 MHz, CDCl3): δ 1.33-1.37 (m, 6H), 1.45-1.49 (m, 2H), 1.55-1.58 (m, 2H), 2.20-2.25 (q, 2H), 3.62-3.66 (t, 2H), 5.79-5.84 (d, J = 15.6 Hz, 1H), 7.03 -7.10 (dt, J = 15.6 Hz, 1H).
Mass spectrum: [M-Na]+ m/z 209 (calculated value: 186)
Melting point: 62.5 ± 1°C.
References
[1] Patent: US2008/281114, 2008, A1. Location in patent: Page/Page column 11
[2] Patent: US2014/249105, 2014, A1. Location in patent: Paragraph 0247-0252
