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Hydroxycapric Acid is a specialized saturated fatty acid that is a minor constituent of royal jelly.
Hydroxycapric Acid was discovered in 1957.
A Hydroxycapric Acid, omega-hydroxy fatty acid, shown to be the preferred hydroxylation product (together with the 9-OH isomer) of capric acid in biosystems, and used as a standard in lipid assays; reported to have cytotoxic effects.
CAS: 1679-53-4
MF: C10H20O3
MW: 188.26
EINECS: 216-848-1
Synonyms
10-Hydroxycapricacid;10-HYDROXYDECANOIC ACID;10-Hydroxydecanoic acid (Synonyms: NSC 15139);1-Hydroxydecanoic acid;10-Hydroxydecanoic acid (NSC 15139);Decanoic acid, 10-hydroxy-;10-HYDROXY-DECYLIC ACID;10-HYDROXYDECANOIC ACID 95%
Hydroxycapric Acidis a saturated fatty acid of hydroxy-trans-2-decenoic acid (10H2DA).
Hydroxycapric Acid's molecule has two functional groups (-OH and -COOH).
Hydroxycapric Acid has been reported to prevent the lipopolysaccharide-induced NO production in murine macrophages.
Hydroxycapric Acid has been extracted from royal jelly obtained from honeybees (Apis mellifera) and exhibits estrogenic action.
Hydroxycapric Acid's polymerization with the polyethylene glycol-modified lipase in a transparent benzene solution has been reported to proceed by the formation of ester linkage.
Hydroxycapric Acid is a synthetic or natural, 10-carbon hydroxy acid used in skincare as a skin-conditioning and occlusive agent.
Hydroxycapric Acid helps maintain skin health and can be found in products like lotions.
Hydroxycapric Acid is generally considered low-risk for irritation and, in some forms, acts as a fatty acid in biological systems.
Hydroxycapric Acid, with the CAS number 1679-53-4, is a fatty acid characterized by a hydroxyl group (-OH) located at the tenth carbon of a decanoic acid chain.
Hydroxycapric Acid is a white, waxy solid at room temperature and is soluble in organic solvents but has limited solubility in water due to its hydrophobic alkyl chain.
Hydroxycapric Acid is known for its potential applications in various fields, including cosmetics, pharmaceuticals, and as a surfactant.
The presence of the hydroxyl group imparts unique properties, such as increased reactivity and the ability to form hydrogen bonds, which can enhance its functionality in formulations.
Additionally, Hydroxycapric Acid is recognized for its antimicrobial properties, making it a candidate for use in preserving products or as an active ingredient in topical formulations.
Hydroxycapric Acid's structural characteristics and functional groups contribute to its versatility in chemical reactions and applications in material science and biochemistry.
Hydroxycapric Acid is a nonsteroidal anti-inflammatory drug that has the ability to inhibit prostaglandin synthesis.
Hydroxycapric Acid has been shown to be effective in treating inflammatory diseases such as arthritis and psoriasis.
Hydroxycapric Acid is also used to treat lacrimal gland inflammation, and caco-2 cells have been shown to have a maximal response to this drug.
Hydroxycapric Acid is synthesized from trans-10-hydroxy-2-decenoic acid by an acylation reaction with silver ions in a nonpolar solvent, followed by heating.
Hydroxycapric Acid can be separated from other fatty acids using an analytical technique called thin layer chromatography (TLC).
Hydroxycapric Acid impurity profile requires careful analytical characterization to ensure raw material quality and consistency.
As a hydroxy fatty acid, common impurities include chain-length homologues, positional isomers, dehydration products, and low-level oxidation or lactonization derivatives formed during synthesis, storage, or acid-catalyzed processing.
Identification and quantification are performed by validated HPLC, GC-MS, LC-MS and NMR methods with stability studies to track impurity evolution.
Robust control strategies encompass purification, inert handling, antioxidant inclusion and defined specification limits supported by batch-level impurity profiles and certificates of analysis for regulatory and quality assurance purposes.
Hydroxycapric Acid Chemical Properties
Melting point: 75-77 °C (lit.)
Boiling point: 330.8±15.0 °C(Predicted)
density: 1.013±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
solubility: Chloroform (Slightly), Methanol (Slightly)
pka: 4.78±0.10(Predicted)
form: Solid
color: White to Off-White
Cosmetics Ingredients Functions: SKIN CONDITIONING
Cosmetic Ingredient Review (CIR): 10-Hydroxydecanoic acid (1679-53-4)
InChI: InChI=1S/C10H20O3/c11-9-7-5-3-1-2-4-6-8-10(12)13/h11H,1-9H2,(H,12,13)
InChIKey: YJCJVMMDTBEITC-UHFFFAOYSA-N
LogP: 1.847 (est)
CAS DataBase Reference: 1679-53-4(CAS DataBase Reference)
NIST Chemistry Reference: Hydroxycapric Acid(1679-53-4)
Uses
Hydroxycapric Acid is suitable for use in a study on Novozym 435-catalyzed condensation polymerization of cis-9,10-epoxy-18-hydroxyoctadecanoic acid and its comparison with corresponding polymerization of 10-hydroxydecanoic acid.
Synthesis
The alkaline cleavage of ricinoleates may be carried out in ethanol at temperatures of 190-200℃ using two to three equivalents of NaOH to give yields up to 69% of pure 10-hydroxydecanoic acid.
This method avoids the use of large excesses of alkali as well as the use of high boiling alcohols as reaction media.
In a typical experiment we placed 46.8 g (150 mmoles) of methyl ricinoleate and a solution of 12.0 g (300 mmoles) of NaOH in 100 ml of 95% ethanol.
The autoclave was placed in an oven at 190-200℃ for 16-18 hr and then cooled to room temperature, vented to remove a certain amount of ethylene (identified by its mass spectrum) produced during heating and opened.
After dissolving the semisolid contents in about 500 ml of water, the resulting solution was extracted with three 200 ml portions of ether to remove neutral material.
This step may be omitted if Hydroxycapric Acid is not desired to retain the 2-octanol formed as coproduct.
The aqueous phase was then acidified with 30 ml of concentrated hydrochloric acid, and the liberated acids extracted with two 200 ml portions of ether.
After drying over magnesium sulfate and evaporation under reduced pressure to give about 35 g of solid, the crude acids were then dissolved in 100 ml of warm ethyl acetate and 100 ml of heptane was added.
After standing overnight at 0℃ the mixture deposited 20.2 g of crystals, mp 71.5-74.5℃ which on recrystallization from benzene, 140 ml, yielded 19.4 g (104 mmoles, 69%) of Hydroxycapric Acid, mp 73-75℃ (lit. 75-76℃).
The above conditions are optimal when methyl ricinoleate is utilized, but the cleavage will proceed at lower temperatures.
At 160 C about 41% yield of product was obtained after approximately the same reaction time.
