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Docosahexaenoic Acid

CAS No.
6217-54-5
Chemical Name:
Docosahexaenoic Acid
Synonyms
DHA;doconexent;CIS-4,7,10,13,16,19-DOCOSAHEXAENOIC ACID;DHA algal oil;DOCOSAHEXANOIC ACID;CERVONIC ACID;Single-Use Docosahexaenoic Acid (peroxide free);(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid;zhaoyou;Ropufa 60
CBNumber:
CB4128690
Molecular Formula:
C22H32O2
Molecular Weight:
328.49
MDL Number:
MFCD00065722
MOL File:
6217-54-5.mol
MSDS File:
SDS
Last updated:2023-11-27 13:03:33

Docosahexaenoic Acid Properties

Melting point -44°C
Boiling point 446.7±24.0 °C(Predicted)
Density 0.943±0.06 g/cm3(Predicted)
refractive index 1.5030-1.5060
Flash point 62°C
storage temp. -20°C
solubility Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Heated, Sonicated)
pka 4.58±0.10(Predicted)
form Oil
color Clear colorless to light yellow
Merck 14,3398
BRN 1715505
Stability Light and Air Sensitive
InChIKey MBMBGCFOFBJSGT-UAYLQDFESA-N
LogP 6.778 (est)
CAS DataBase Reference 6217-54-5(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII ZAD9OKH9JC
NCI Drug Dictionary doconexent
NIST Chemistry Reference Doconexent(6217-54-5)
EPA Substance Registry System Docohexanenoic Acid (6217-54-5)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS02,GHS07
Signal word  Danger
Hazard statements  H225-H319
Precautionary statements  P210-P305+P351+P338
Safety Statements  23-24/25
RIDADR  UN1170 - class 3 - PG 2 - Ethanol, solution
WGK Germany  3
8-10-23
HS Code  29161900
NFPA 704
3
2 0

Docosahexaenoic Acid price More Price(43)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich D2534 cis-4,7,10,13,16,19-Docosahexaenoic acid ≥98% 6217-54-5 1g $618 2024-03-01 Buy
Sigma-Aldrich D-117 cis-4,7,10,13,16,19-Docosahexaenoic acid 500?μg/mL in ethanol, certified reference material, Cerilliant? 6217-54-5 1mL $154 2022-05-15 Buy
TCI Chemical D2226 cis-4,7,10,13,16,19-Docosahexaenoic Acid >97.0%(GC) 6217-54-5 100mg $149 2024-03-01 Buy
Cayman Chemical 90310 Docosahexaenoic Acid ≥98% 6217-54-5 50mg $44 2024-03-01 Buy
Sigma-Aldrich D2534 cis-4,7,10,13,16,19-Docosahexaenoic acid ≥98% 6217-54-5 25mg $59.6 2024-03-01 Buy
Product number Packaging Price Buy
D2534 1g $618 Buy
D-117 1mL $154 Buy
D2226 100mg $149 Buy
90310 50mg $44 Buy
D2534 25mg $59.6 Buy

Docosahexaenoic Acid Chemical Properties,Uses,Production

Description

Docosa Hexaenoic acid (DHA) is an omega-3 fatty acid that is a primary structural component of the human brain, cerebral cortex, skin, sperm, testicles and retina. It can be synthesized from alphalinolenic acid or obtained directly from maternal milk or fish oil. DHA's structure is a carboxylic acid(~oic acid) with a 22-carbon chain (docosa- is Greek for 22) and six (Greek "hexa") cis double bonds (-en~); the first double bond is located at the third carbon from the omega end. Its trivial name is cervonic acid, its systematic name is all-cis-docosa-4,7,10,13,16,19-hexa-enoic acid, and its shorthand name is 22:6(n-3) in the nomenclature of fatty acids.

Docosahexaenoic Acid

Application

DHA is used as a supplement for premature babies and as an ingredient in baby formula during the first year of life to promote better mental development. It is also used in infant formula to prevent lung diseases, allergic diseases such as eczema or hay fever, and diarrhea. This practice probably started because DHA is found naturally in breast milk. In some cases, DHA is used in combination with arachidonic acid. DHA is also taken by mouth alone or along with EPA to improve mental function in healthy people or those with mental impairment. It is also used to improve mental function in people with dementia or age-related mental decline. It is also taken by mouth for attention deficit-hyperactivity disorder (ADHD), depression, aggressive behavior, Alzheimer's disease, autism, and to prevent relapse in schizophrenic patients who stop taking antipsychotic medication. DHA is also taken by mouth for diabetes, coronary artery disease (CAD), stroke, high levels of cholesterol and fats in the blood, high blood pressure, and cancer including breast and prostate cancer. It is also used for a type of fatty liver not related to drinking alcohol, obesity, ear infections, and learning problems in children. Some people use DHA is for improving vision, preventing an eye disease called age-related macular degeneration (AMD), treating an eye condition called retinitis pigmentosa, and increasing DHA levels in people with cystic fibrosis. DHA is taken by mouth in combination with eicosapentaenoic acid (EPA) for a variety of conditions, including the prevention and reversal of heart disease, stabilizing heart rhythm, preventing abnormal heart beats after heart surgery, painful menstrual periods, lupus, and certain kidney diseases. EPA and DHA are also used in combination for preventing migraine headaches in teenagers, Behcet's syndrome, psoriasis, Raynaud's syndrome, rheumatoid arthritis, bipolar disorder, and ulcerative colitis.

Biosynthesis of DHA

ALA is an essential fatty acid. It is synthesised in plants and in many lower organisms and is found in the human diet mainly as a component of green leaves, some nuts, seeds and vegetable oils, and foods made from or containing those ingredients. There is a metabolic pathway that links ALA to DHA. This pathway involves a series of enzyme-catalysed elongation and desaturation reactions. Elongation enzymes, called elongases, add pairs of carbon atoms to the growing acyl chain, in this case converting an 18-carbon fatty acid into a 22-carbon one, while desaturase enzymes insert double bonds into the acyl chain, in this case converting a fatty acid with 3 double bonds in its acyl chain into one with 6 double bonds. These reactions occur predominantly within the endoplasmic reticulum. The pathway is believed to mainly occur within the liver, but there is some evidence that other tissues, including brain and testis, have high expression of the genes encoding the relevant enzymes.

Description

Docosahexaenoic acid (DHA) is a long-chain ω-3 polyunsaturated fatty acid (PUFA) found in fish and algal oils. It comprises approximately 40% of total brain PUFAs and is abundant in grey matter and retinal membranes. DHA typically represents 0.52-7.5% of human total plasma fatty acids. It is produced from α-linolenic acid (ALA; Item Nos. 90210 | 21910) via a series of desaturase- and elongase-catalyzed reactions, resulting in a docosapentaenoic acid (DPA; ) intermediate, which is elongated, desaturated, and β-oxidized to produce DHA. DHA can be liberated from cellular membranes by phospholipase A2 (PLA2) and converted to numerous oxylipins, including specialized pro-resolving mediators (SPMs), which are produced by lipoxygenases and include D-series protectins and resolvins, as well as maresins, that regulate host defense and the resolution of inflammation. DHA has roles in several physiological and pathological processes, including neural development, cardiovascular diseases, obesity, and inflammation.

DHA MaxSpec® standard is a quantitative grade standard of DHA that has been prepared specifically for mass spectrometry and related applications where quantitative reproducibility is required. The solution has been prepared gravimetrically and is supplied in a deactivated glass ampule sealed under argon. The concentration was verified by comparison to an independently prepared calibration standard. The verified concentration is provided on the certificate of analysis. This DHA MaxSpec® standard is guaranteed to meet identity, purity, stability, and concentration specifications and is provided with a batch-specific certificate of analysis. Ongoing stability testing is performed to ensure the concentration remains accurate throughout the shelf life of the product. Note: The amount of solution added to the vial is in excess of the listed amount. Therefore, it is necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.

Chemical Properties

Clear Colourless Liquid

Occurrence

Ordinary types of cooked salmon contain 500 – 1500 mg DHA and 300–1000 mg EPA per 100 grams.(USDA) Additional top fish sources of DHA are: tuna, bluefish, mackerel, swordfish, anchovies, herring, sardines, and caviar.
The discovery of algae - based DHA
In the early 1980s, NASA sponsored scientific research in search of a plant-based food source that could generate oxygen and nutrition on long-duration space flights. The researchers discovered that certain species of marine algae produced rich nutrients. This research led to the development of an algae-based, vegetable-like oil that contains two essential polyunsaturated fatty acids: DHA and ARA (Arachidonic acid).
Use as a food additive
DHA is widely used as a food supplement. It was first used primarily in infant formulas. In 2004, the US Food and Drug Administration endorsed qualified health claims for DHA , and by 2007 DHA - fortified dairy items (milk, yogurt, cooking oil) started to appear in grocery stores.
DHA is believed to be helpful to people with a history of heart disease, for premature infants, and to support healthy brain development especially in young children along with supporting retinal development. Some manufactured DHA is a vegetarian product extracted from algae, and it competes on the market with fish oil that contains DHA and other omega-3's such as EPA. Both fish oil and DHA are odorless and tasteless after processing as a food additive.
Studies of vegetarians and vegans
Vegetarian diets typically contain limited amounts of DHA, and vegan diets typically contain no DHA. Vegetarians and vegans have substantially lower levels of DHA in their bodies, and short-term supplemental ALA has been shown to increase EPA, but not DHA. However, supplemental preformed DHA, available in algae-derived oils or capsules, has been shown to increase DHA levels. While there is little evidence of adverse health or cognitive effects due to DHA deficiency in adult vegetarians or vegans, fetal and breast milk levels remain a concern.
DHA and EPA in fish oils
Fish oil is widely sold in gelatin capsules containing a mixture of omega-3 fatty acids including EPA and smaller quantities of DHA. One study found fish oil higher in DHA than EPA lowered inflammatory cytokines, such as IL-6 and IL-1β, associated with neurodegenerative and autoimmune diseases. They note the brain normally contains DHA, but not EPA, though both DHA and EPA plasma concentrations increased significantly for participants.

Uses

Omega-3 fatty acid found in marine fish oils and in many phospholipids. Major structural component of excitable membranes of the retina and brain; synthesized in the liver from a-linolenic acid. Nutritional supplement.

Uses

Docosahexaenoic acid is found in fish oils in nature. It is also commercially manufactured from microalgae; Crypthecodinium cohnii and Schizochytrium.

Uses

Nutritional supplement.

Definition

ChEBI: A docosahexaenoic acid having six cis-double bonds at positions 4, 7, 10, 13, 16 and 19.

General Description

An omega-3 fatty acid essential for normal brain growth and

function, docosahexaenoic acid (DHA) plays an important role as a signaling factor in cells for both anti- and pro-inflammatory processes. Levels of docosahexaenoic acid as well as other fatty acids are analyzed by GC/MS or LC-MS/MS methods to monitor patients undergoing diet therapy for mitochondrial or peroxisomal disorders. This Certified Spiking Solution? is suitable for use as starting material in the

preparation of linearity standards, calibrators, or controls in mass spectrometry-based DHA testing applications such as assessment of cardiovascular disease risk and fatty acid deficiency, and detection and quantification of DHA in nutraceuticals and dietary supplements.

Biological Activity

Endogenous omega-3 fatty acid. Acts as a selective retinoid X receptor (RXR) agonist that displays no activity at RAR, thyroid hormone receptor or the vitamin D receptor (VDR). Activates all three RXR isoforms. Also shown to inhibit A β 1-42 fibrillation and toxicity in vitro .

Biochem/physiol Actions

Docosahexaenoic acid, DHA, is an omega-3 polyunsaturated fatty acid with 22 carbons and six double bonds, the first double bond occuring at position three from the methyl terminus (22:6 n-3). DHA is a component of lipid membranes and the myelin sheath. DHA also serves as a precursor for signaling molecules such as prostaglandins and eicosanoids.

storage

Store at -20°C

Purification Methods

Its solubility in CHCl3 is 5%. It has been purified from fish oil by GLC using Ar as mobile phase and EGA as stationary phase with an ionisation detector [UV: Stoffel & Ahrens J Lipid Res 1 139 1959], and via the ester by evaporative "molecular" distillation using a 'continuous molecular still' at 10-4 mm with the highest temperature being 110o and a total contact time with the hot surface being 60sec [Farmer & van den Heuvel J Chem Soc 427 1938]. The methyl ester has b 208-211o/2mm, d4 0.9398, 20 1.5035. nD With Br2 it forms a dodecabromide m ca 240o(dec). Also, the acid was converted to the methyl ester and purified through a three-stage molecular still [as described by Sutton Chem Ind (London) 11383 1953] at 96o, and the rate was adjusted so that one-third of the material was removed each cycle of three distillations. The distillate (numbered 4) (13g) was dissolved in EtOH (100mL containing 8g of KOH) at -70o and set aside for 4hours at 30o with occasional shaking under a vacuum. Water (100mL) was added and the solution was extracted with pentane, washed with HCl, dried (MgSO4), filtered and evaporated to give a clear oil (11.5g) m -44.5o to -44.1o. In the catalytic hydrogenation of the oil six mols of H2 are absorbed and docosanoic acid (behenic acid) is produced with m 79.0-79.3o undepressed with an authentic sample (see docosanoic acid below) [Whitcutt Biochem J 67 60 1957]. [Beilstein 2 IV 1812.]

Docosahexaenoic Acid Preparation Products And Raw materials

Global( 478)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Mojin Biotechnology Co., Ltd
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Hebei Lingding Biotechnology Co., Ltd.
+86-18031140164 +86-19933155420 erin@hbldbiotech.com China 885 58
Nantong Guangyuan Chemicl Co,Ltd
+undefined17712220823 admin@guyunchem.com China 616 58
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008657128800458; +8615858145714 fandachem@gmail.com China 9359 55
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View Lastest Price from Docosahexaenoic Acid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
DHA pictures 2024-03-08 DHA
6217-54-5
US $10.00 / kg 1kg 99% 1000kg Nantong Guangyuan Chemicl Co,Ltd
Docosahexaenoic Acid pictures 2023-11-27 Docosahexaenoic Acid
6217-54-5
US $90.00 / KG 1KG 99% 9000kg/per week Hebei Lingding Biotechnology Co., Ltd.
Docosahexaenoic Acid pictures 2023-08-31 Docosahexaenoic Acid
6217-54-5
US $100.00 / bag 1bag 99 5000 Hebei Fengqiang Trading Co., LTD
  • DHA pictures
  • DHA
    6217-54-5
  • US $10.00 / kg
  • 99%
  • Nantong Guangyuan Chemicl Co,Ltd
Docosahexaenoicacid,97 DOCOSAHEXAENOIC ACID(DHA) cis-4,7,10,13,16,19-DocosahexaenoicAcid(stabiliz CIS-4,7,10,13,16,19-DOCOSA-PENTAENOIC ACID 4,7,10,13,16,19-Docosahexaenoic acid, (4Z,7Z,10Z,13Z,16Z,19Z)- CIS-4,7,10,13,16,19-DOCOSAHEXAENOICACID(OIL) CIS-4,7,10,13,16,19-DOCOSAHEXAENOICACID(POWDER) (4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-Docosahexaenoic acid Doesahexaenoic acid (DHA) ALL CIS 4-7-10-13-16-19 DOCOSAHEXAENOIC ACID cis-4,7,13,16,19-Docosahexaenoic acid (stabilized with vitamine E) (4Z,7E,10E,13E,16E,19E)-docosa-4,7,10,13,16,19-hexaenoic acid DOCOSAHEXAENOIC ACID(DHA)(AS) Docosahexaenoic acid (DHA)-d5 Docosa-4Z,7Z,10Z,13Z,16Z,19Z-hexaenoic Acid (22:6, n-3) DHA (cis-4,7,10,13,16,19-Docosahexaenoic acid) DHA (Docosahexaenoic Acid) Docosahexaenoic Acid Powder CIS-4,7,10,13,16,19-DOCOSAHEXAENOICA 4,7,10,13,16,19-Docosahexaenoic acid (all-cis) cis-4,7,10,13,16,19-Docosahexaenoic acid,DHA 4Z,7Z,10Z,13Z,16Z,19Z-DOCOSAHEXAENOIC ACID 4C,7C,10C,13C,16C,19C-DOCOSAHEXAENOIC ACID ALL CIS 4-7-10-13-16-19 DHA (all-Z)-4,7,10,13,16,19-Docosahexaenoic Acid Marinol D 50TG Ropufa 60 Docosahexaencic acid 22:6(n-3) all-cis-docosa-4,7,10,13,16,19-hexaenoic acid cis-4,7,10,13,16,19-Docosahexaenoic acid,98% DOCOSAHEXAENOIC ACID(DHA, froM Microalgae DHA 4C,7C,10C,13C,16C,19C CIS-4,7,10,13,16,19-DOCOSAHEXANOIC ACID CIS-4,7,13,16,19-DOCOSAHEXAENOIC ACID DOCOSA-4Z,7Z,10Z,13Z,16Z,19Z-HEXAENOIC ACID DOCOSA-4Z,7Z,10Z,13Z,16Z,19Z-HEXANEOIC ACID C22:6, (ALL CIS-4,7,10,13,16,19) OMEGA-3 FATTY ACID Docosahexaenoic Acid DHA 10% Twenty-two carbon six acid (DHA) DHA oil (from fermentation) cis-4,7,10,13,16,19-Docosahexaenoic Acid(Dha-M)(C22:6) Docosahexaenoic Acid MaxSpec Standard zhaoyou Docosahexaenoic acid DHA 6217-54-5 Docosahexaenoic Acid (DHA Oil) cis-4,7,10,13,16,19-Docosahexaenoic acid - 95%min cis-4,7,10,13,16,19-DocosahexaenoicAcid> Dry Docosahexaenoic Acid cis-4,7,10,13,16,19-Docosahexaenoic acid Solution, 100μg/mL Docosahexaenoicaci Docosahexaenoic Acid (Omega 3) Algal oil DHA doxonexent Pharmaceutical Intermediate DHA Powder CAS?6217-54-5?Docosahexaenoic Acid cis-4,7,1,13,16,19-Docosahexaenoic acid Docosahexaenoic acidQ: What is Docosahexaenoic acid Q: What is the CAS Number of Docosahexaenoic acid Q: What is the storage condition of Docosahexaenoic acid Q: What are the applications of Docosahexaenoic acid Docosahexaenoic acid(6217-54-5)