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Product name: Docosahexaenoic acid
Synonym name: DHA; cis-4,7,10,13,16,19-Docosahexaenoic acid
Catalogue No.: BP4144
Cas No.: 6217-54-5
Formula: C22H32O2
Mol Weight: 328.496
Botanical Source:
Physical Description:
Type of Compound: Aliphatics
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
For Reference Standard and R&D, Not for Human Use Directly.
HPLC of Docosahexaenoic acid
HNMR of Docosahexaenoic acid
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
37.3000
6.3354
3.9331
.0063
4.8735
4.1959
High
96.1161
3.1986
Yes
Yes
No
No
No
No
0.0
No
Yes
Yes
Yes
Docosahexaenoic acid (DHA) is a long-chain ω-3 polyunsaturated fatty acid with the molecular formula C22H32O2, molecular weight 328.4960, CAS number 6217-54-5. With its unique biological functions and broad physiological activity, DHA has become an important research subject in the field of natural product pharmacology. As the most abundant fatty acid in the brain and retina, DHA plays a key role in the development, function maintenance, and disease prevention and treatment of the nervous system. Its main sources include fish oil, breast milk, and certain algae. Due to its contributions to neuroprotection, anti-inflammation, and anti-tumor activities, DHA has become a hotspot in nutritional supplements and drug development.
This paper systematically reviews the chemical structure and physicochemical properties of DHA, its natural sources and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics, and explores its clinical application prospects and future development directions, aiming to provide a theoretical foundation and reference for pharmacological research of natural products and related drug development.
The chemical name of DHA is All-cis-docosa-4,7,10,13,16,19-hexaenoic acid. Its structural features include 22 carbon atoms and 6 cis double bonds, located at positions 4, 7, 10, 13, 16, and 19 of the carbon chain. In its molecular structure, all six double bonds are cis-type (Z-type), endowing the molecule with high flexibility and unsaturation, which greatly affects its biological activity and membrane lipid properties.
In terms of physicochemical properties, DHA has a molecular weight of 328.4960 and a LogP value of 6.3354, indicating strong lipid solubility. Its polar surface area (TPSA) is 37.3 Ų, with extremely low water solubility (0.0063 mg/mL), which matches the hydrophobicity of its long-chain fatty acids. DHA has excellent ability to penetrate the blood-brain barrier, making it suitable for the development of drugs related to the nervous system. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity; The Ames mutagenic test was 0.0, indicating a low genotoxicity risk.
Although DHA is mainly found in marine fish oils, its original source was certain microalgae. Algae produce DHA through biosynthesis, and fish enrich their bodies by ingesting algae. Breast milk also contains a high amount of DHA, which is especially crucial for infant neurological development in the early breastfeeding period.
The main raw materials for industrial DHA extraction include deep-sea fish oil (such as salmon and cod liver oil) and algae oil. Extraction methods mostly use solvent extraction, supercritical CO2 extraction, and enzymatic purification techniques. Supercritical CO2 extraction has become the mainstream technology for extracting DHA in recent years due to its environmental friendliness, efficiency, and strong selectivity. Algal fermentation culture membrane separation technology has also been widely researched for producing high-purity DHA.
DHA's pharmacological activities cover neuroprotection, anti-inflammation, anti-tumor, and metabolic regulation.
Neuroprotective effects
DHA is the main omega-3 fatty acid in brain tissue, involved in the construction and functional regulation of neuronal membranes. Numerous animal and cell experiments have shown that DHA can promote neuron survival, inhibit neuroinflammation, and slow the progression of neurodegenerative diseases. It demonstrates significant protective effects in models of neurological diseases such as Alzheimer's and Parkinson's disease.
Anti-inflammatory effects
DHA regulates inflammatory signaling pathways, inhibits the release of pro-inflammatory factors, promotes the production of anti-inflammatory mediators, and exerts immune regulation functions. Its metabolites, such as DHA-derived neuroprotectins and resolvins, play important roles in resolving inflammation.
Anti-tumor effects
Research has found that DHA can inhibit the proliferation and migration of various tumor cells, induce tumor cell apoptosis, and enhance the sensitivity of chemotherapy drugs. Its mechanisms involve lipid remodeling of cell membranes, regulation of oxidative stress, and intervention in signal transduction pathways.
Metabolic regulation
DHA participates in lipid metabolism and energy balance, improves insulin sensitivity, lowers blood lipid levels, and has potential preventive and therapeutic value for metabolic syndrome and diabetes.
DHA's multiple pharmacological effects are mainly achieved by regulating a series of key molecular targets, with particularly outstanding performance in the field of neuroprotection.
The regulation of these targets together constructs a multi-level, multi-pathway neuroprotective network for DHA.
Druggability evaluation of DHA indicates good drug development potential. Its high lipid solubility (LogP=6.3354) and low polarity surface area make it easy to cross the blood-brain barrier, making it suitable for treating neurological diseases. Low water solubility is one of the challenges in formulation development, requiring improved bioavailability through technologies such as liposomes and nanocarriers.
Toxicological evaluation showed that DHA had no significant hERG channel inhibition and was safe for the heart; Ames test negative, low genotoxicity risk, and relatively high safety. Pharmacokinetic studies show that DHA can be effectively absorbed by the intestines after oral intake and preferentially distributed to brain tissue and retina, with a long half-life, making it suitable for long-term supplementation.
As a natural omega-3 fatty acid, DHA has been widely used in the field of nutritional supplements, especially in infant formula and brain health products. Clinical research on neurodegenerative diseases, depression, and retinal disorders continues to deepen, demonstrating promising therapeutic potential.
In the future, with the development of nanodrug carriers and targeted delivery technologies, the bioavailability and targeting of DHA will further improve, promising to expand its applications in neurological diseases, tumors, and metabolic diseases. In addition, the combined application strategy of DHA with other drugs is also worth exploring in depth to achieve synergistic therapeutic effects.
At the same time, research based on DHA metabolites will provide new ideas for the design of novel neuroprotective agents. Through structural modification and pharmacodynamic optimization, developing efficient and safe DHA-derived drugs will become a key focus of future research.
Docosasix enoic acid (DHA), as a key omega-3 fatty acid, shows broad application prospects in neuroprotection, anti-inflammation, anti-tumor, and metabolic regulation fields due to its unique chemical structure and rich biological activity. Its mechanism of action involves multiple molecular targets, forming a complex regulatory network that supports its multi-target and multi-pathway pharmacological effects. Druggability evaluations show that DHA has good safety and blood-brain barrier penetration, but poor water solubility and low bioavailability remain challenges in formulation development.
In the future, combined with modern drug delivery technologies and molecular design, DHA and its derivatives are expected to become important natural drug resources for the treatment of neurological diseases and other chronic illnesses. Ongoing and in-depth basic and clinical research will promote the application of DHA in precision medicine and personalized treatment, facilitating the transition from nutritional supplementation to drug therapy to benefit more patients.
Shenshuai
Wenjing
Hedandan
