PRODUCTS

STEARIDONIC ACID (SDA)

EC / List no.: 606-502-1
CAS no.: 20290-75-9

Stearidonic acid (SDA) is an ω-3 fatty acid, sometimes called moroctic acid.
Stearidonic acid (SDA) is biosynthesized from alpha-linolenic acid by the enzyme delta-6-desaturase.
Natural sources of this fatty acid are the seed oils of hemp, blackcurrant, corn gromwell, and Echium plantagineum, and the cyanobacterium Spirulina.
Stearidonic acid (SDA) can also be synthesized in a lab.
A GMO soybean source is approved by the European Food Safety Authority.

Stearidonic acid is an 18-carbon containing polyunsaturated fatty acid (PUFA).
Stearidonic acid (SDA) belongs to the class of ω-3 fatty acids, which are dietary precursors to eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA).
Stearidonic acid is present in small amounts in seed oils.
An 18-carbon, ω-3 fatty acid which is a dietary precursor to eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA).
Stearidonic acid is present in small amounts in seed oils.

Description
Stearidonic acid (SDA) is an ω-3 fatty acid, sometimes called moroctic acid.
Stearidonic acid (SDA) is biosynthesized from alpha-linolenic acid by the enzyme delta-6-desaturase.
Natural sources of this fatty acid are the seed oils of hemp, blackcurrant, corn gromwell and echium, and the cyanobacterium Spirulina.

Chemical Properties
Light Yellow Oil

Uses:
Stearidonic Acid onic acid is present in small amounts in seed oils.
A 18-carbon, ω-3 fatty acid which is a dietary precursor to eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). Stearidonic acid is present in small amounts in seed oils.

Definition
ChEBI: An octadecatetraenoic acid having four double bonds located at positions 6, 9, 12 and 15 (the all-cis-isomer).
Stearidonic acid (SDA) has been isolated from Lithospermum officinale and fish oils.

Biochem/physiol Actions
Stearidonic acid is an 18-carbon containing polyunsaturated fatty acid (PUFA).
Stearidonic acid (SDA) belongs to the class of ω-3 fatty acids, which are dietary precursors to eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA).
Stearidonic acid is present in small amounts in seed oils.

Stearidonic acid (SDA), a long-chain omega-3 fatty acid (C18:4) with a range of health benefits, could be a game-changer in supplements and foods.
Stearidonic acid (SDA) offers a clean label, and it is also vegan, traceable and may offer a highly scalable pathway to meeting omega-3 recommended daily intakes.
This article provides a brief overview on the basics about Stearidonic acid (SDA) and its rising importance in omega nutrition.

Stearidonic acid (SDA) in Omega-3 Metabolism

Significant dietary Stearidonic acid (SDA) is commercially available only from vascular plant origins, although it occurs naturally at low levels (0.5 to 2 percent, typically) in edible oily fish. Metabolically, Stearidonic acid (SDA) is synthesized by humans from dietary alpha-linolenic acid (ALA, C18:3), a more widely abundant omega-3 found in some seed and nut oils such as flax and chia.
ALA is converted into Stearidonic acid (SDA) by delta-six desaturase (Δ6D), an enzyme originating in the liver.
While critical to the synthesis of very long chain omega-3s, this enzymatic conversion is particularly inefficient in humans.
Stearidonic acid (SDA) is then further converted to the widely studied and well-known omega-3 eicosapentaenoic acid (EPA, C20:5).
Human cell membranes require the highly unsaturated fatty acids to be incorporated as phospholipids in order to maintain proper fluidity, porosity and integrity, and to serve as reservoirs of anti-inflammatory response mediators.
While Stearidonic acid (SDA) is itself a product of ALA metabolism, direct dietary Stearidonic acid (SDA) intake offers people a much more efficient way to synthesize EPA from non-marine sources.

As such, Stearidonic acid (SDA) has been dubbed a “pro-EPA" omega-3 fatty acid because it bypasses the Δ6D rate-limiting step in humans that causes plant-derived ALA sources to convert poorly to the more elongated omega-3 fatty acids EPA, DPA (C22:5) and DHA (C22:6).
Clinical studies have shown that while Stearidonic acid (SDA) does not convert to DHA to any significant degree, Stearidonic acid (SDA) converts to EPA in tissues and circulating cells up to five times more efficiently than ALA.
Further, because Stearidonic acid (SDA) is less unsaturated than EPA and DHA, it is more stable, less prone to oxidation, and therefore more amenable in a wide variety of food and beverage applications where resulting “fishy" off-flavors present challenges to palatability and consumer acceptance.

Stearidonic Acid (SDA) is an omega-3 fatty acid with 18 carbons and 4 double bonds, which is commonly notated as C18:4n-3 or simply 18:4n-3.
Stearidonic acid (SDA) is found in several plants and many fish.

Genetically Engineered Stearidonic acid (SDA) Omega-3 Soybeans
With the increased awareness of the importance of omega-3 fatty acids, particularly EPA and DHA, in the diet, Monsanto created a genetically engineered Stearidonic acid (SDA) Omega-3 Soybean known as MON 87769.
Plant foods, including soybeans, often contain omega-3s in the form of alpha linolenic acid (ALA).
However, the optimal form of omega-3s are considered to be eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA).

Studies have shown that the conversion of ALA to the more desirable long chain PUFAs [poly unsaturated fatty acids], EPA and DHA, found in fatty fish and algae, is inefficient in humans.
As a result, studies have shown that it can take 14-20 grams of ALA to convert to 1 gram EPA (James et al., 2003).
Stearidonic acid (SDA) is an eighteen carbon fatty acid with four double bonds (18:4n-3) that is naturally found in fish and fish/algal oil products and some plants.
Stearidonic acid (SDA) is the intermediate in the biochemical pathway between ALA and EPA and does not require the action of delta-6 desaturase for conversion to EPA.
As a result, conversion of Stearidonic acid (SDA) to EPA is much more efficient.

Sources of Stearidonic Acid
Stearidonic acid is not commonly found in plants, but it is found in the following plants:

Black Currant seeds, Ribes Nigrum: 2.5%-4.5% SDA[2]
Borage seed, Borago offinalis: 0.5% SDA
Hemp seed, Cannabis sativa: Up to 2% SDA
Plants in the genus Echium (in the Borage family) often contain SDA, in amounts exceeding 20% in some species[3][5]
E. asperrimum: 21.06%
E. boissieri: 14.31%
E. creticum: 14.73%
E. sabulicola: 14.72%
Asperuco procumbens (Borage family): 11.75% SDA
Buglossoides arvensis (Borage family): 14.08% SDA
Primula spp.: 11-14%

Stearidonic acid or Stearidonic acid (SDA) (18 carbon atoms) is an essential polyunsaturated fatty acid or PUFA, with four cis (Z) double bounds (the first one from the methyl end is in omega-3 (ω-3) or n-3 so in shorthand 18:4n-3), member of the sub-group called long chain fatty acids (LCFAs), from 14 to 18 carbon atoms.

Properties
Molecular weight: 276.41372 g/mol
Molecular formula: C18H28O2
IUPAC name: (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid
CAS registry number: 20290-75-9
PubChem: 5312508

Synthesis and metabolism of stearidonic acid
Stearidonic acid is produced de novo from apha-linolenic acid in a desaturation reaction catalyzed by the enzyme Δ6-desaturase, a reaction extremely inefficient in humans (as shown previously in rodents).
On the other hand, dietary and from de novo synthesis stearidonic acid is efficiently converted in eicosapentaenoic acid or EPA and docosapentaenoic acid or DPA by the subsequent actions of elongase (it catalyzes the addition of two carbon atoms from glucose metabolism to lengthen the fatty acid chain) and Δ5-desaturase and for this reasons its use may be a valuable tool for increasing EPA and docosahexaenoic acid (DHA) tissue concentrations.
The further metabolism to DHA depends again on Δ6-desaturase (followed by a β-oxidation) and for this reasons this conversion is limited.

Food sources
Stearidonic acid (SDA) occurs as glycerol ester in the leaf lipids of borage (Borago Offcianalis L., of the Boraginaceae) and in blackcurrant seed oil (3.5%).

Stearidonic Acid (SDA) Producing Soybean MON 87769 differs from its traditional counterpart by the addition of the Pj.D6D and Nc.Fad3 genes and their associated regulatory elements.
The insertion of these genes results in the tissue-targeted expression of the novel PjΔ6D and NcΔ15D proteins on MON 87769.
Tissue-specific expression of these two enzymes creates a shift in the fatty acid metabolic pathways, yielding significant levels of Stearidonic acid (SDA) in the seeds of MON 87769.

Stearidonic acid is described as an n-3 fatty acid, all cis-6,9,12,15 – octadecatetraenoic acid.

Stearidonic acid is present in a several plant seed oils.
The most importance dietary sources of this fatty acid are the seed oils of hemp(2-3%) and blackcurrant (2-4%).

The seed oils of many plants species of the Boraginaceae family contain stearidonic acid between 10% and 20%.

Hempseeds also contain gamma-linolenic acid (GLA).
Both Stearidonic acid and gamma-linolenic acid in conjunction can help treat symptoms of atopic dermatitis and other skin disease.

SYNONYMS:
all-cis-6,9,12,15-Octadecatetraenoic acid
18:4(n-3)
18:4ω3
(6Z,9Z,12Z,15Z)-Octadeca-6,9,12,15-tetraenoic acid
All-cis-octadeca-6,9,12,15-tetraenoic acid
Chebi:32389
6C,9C,12C,15C-OCTADECATETRAENOIC ACID
6Z,9Z,12Z,15Z-OCTADECATETRAENOIC ACID
STEARIDONIC ACID
MOROCTIC ACID
(6E,9E,12E,15E)-octadeca-6,9,12,15-tetraenoic acid
stearidonic acid C18:4
6Z,9Z,12Z,15Z-Octadecatetraenoic acid, all-cis-6,9,12,15-Octadecatetraenoic acid, Moroctic acid
(6Z,9Z,12Z,15Z)-6,9,12,15-Octadecatetraenoic acid
6,9,12,15-Octadecatetraenoic acid, (6Z,9Z,12Z,15Z)-
Stearidonic Acid (Moroctic Acid)
Stearidonic acid
Moroctic acid
20290-75-9
(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid
(6Z,9Z,12Z,15Z)-Octadecatetraenoic acid
UNII-P4CEK3495O
6,9,12,15-Octadecatetraenoic acid
6Z,9Z,12Z,15Z-octadecatetraenoic acid
6,9,12,15-Octadecatetraenoic acid, (6Z,9Z,12Z,15Z)-
P4CEK3495O
CHEBI:32389
C18:4n-3,6,9,12
all-cis-octadeca-6,9,12,15-tetraenoic acid
Morotic acid
6C,9C,12C,15C-Octadecatetraenoic acid
6cis Stearidonic acid
stearidonic acid C18:4
Stearidonic acid, >=99%
SCHEMBL29226
CHEMBL484430
6,9,12,15-octadecatetraenoate
DTXSID20920493
HMS3649J17
Stearidonic acid (18:4(n-3))
111174-40-4
LMFA01030357
ZINC13551720
SR-01000946667
6(Z),9(Z),12(Z),15(Z)-Octadecatetraenoic acid
Q2739877
SR-01000946667-1
UNII-71M78END5S component JIWBIWFOSCKQMA-LTKCOYKYSA-N
UNII-96GS7P39SN component JIWBIWFOSCKQMA-LTKCOYKYSA-N