Linolenic acid
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Linolenic acid
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CAS No:
463-40-1
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Formula:
C18H30O2
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Chemical Name:
Linolenic acid
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Synonyms:
9,12,15-Octadecatrienoic acid,(9Z,12Z,15Z)-;Linolenic acid;9,12,15-Octadecatrienoic acid,(Z,Z,Z)-;(9Z,12Z,15Z)-9,12,15-Octadecatrienoic acid;all-cis-9,12,15-Octadecatrienoic acid;α-Linolenic acid;cis,cis,cis-9,12,15-Octadecatrienoic acid;cis-9,cis-12,cis-15-Octadecatrienoic acid;cis-Δ9,12,15-Octadecatrienoic acid;9,12,15-all-cis-Octadecatrienoic acid;9-cis,12-cis,15-cis-Octadecatrienoic acid;(Z,Z,Z)-Octadeca-9,12,15-trienoic acid;(all-Z)-9,12,15-Octadecatrienoic acid;9Z,12Z,15Z-Octadecatrienoic acid;alpha-Linolenic acid;18:3n-3;BRD-K33396764
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CAS No:
Description
α-Linolenic acid, isolated from seed oils, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1].
Linolenic acid is a clear colorless liquid. (NTP, 1992)|OtherSolid, Liquid|Liquid
Linolenic acid is a clear colorless liquid. (NTP, 1992)|Alpha-linolenic acid is a linolenic acid with cis-double bonds at positions 9, 12 and 15. Shown to have an antithrombotic effect. It has a role as a micronutrient, a nutraceutical and a mouse metabolite. It is an omega-3 fatty acid and a linolenic acid. It is a conjugate acid of an alpha-linolenate and a (9Z,12Z,15Z)-octadeca-9,12,15-trienoate.|Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. It is a component of many common vegetable oils and is important to human nutrition.|Linolenic Acid is an essential fatty acid belonging to the omega-3 fatty acids group. It is highly concentrated in certain plant oils and has been reported to inhibit the synthesis of prostaglandin resulting in reduced inflammation and prevention of certain chronic diseases.|A fatty acid that is found in plants and involved in the formation of prostaglandins.
Linolenic acid Basic Attributes
278.43
278.43
207-334-8
0RBV727H71
2042
DTXSID7025506|DTXSID9029435|DTXSID7075058
C997
2916190090
Characteristics
37.3
5.9
Clear colorless to light yellow Liquid
0.9157 g/cm3 @ Temp: 20 °C
-16.5 °C
231 °C
>230 °F
1.491
H2O: INsoluble
2-8°C
0.05 mm Hg at 257° F (NTP, 1992)
170.7 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|173.07 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|174.88 Ų [M-H]- [CCS Type: DT, Method: stepped-field]|173.9 Ų [M-H]-
Oxidizes in air to form peroxides, which spontaneously ignite. Insoluble in water. Sensitive to heat and moisture.
Acids, Carboxylic
Peroxidizable Compound
LINOLENIC ACID is incompatible with bases, oxidizing agents and reducing agents. Also incompatible with peroxides, oxygen and water. (NTP, 1992)
Safety Information
UN1170 - class 3 - PG 2 - Ethanol
1
36/37/38
26-36-37/39
F;Xi
Stable under normal temperatures and pressures.
P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, P501
H317
This chemical is probably combustible. (NTP, 1992)
|Warning|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P302+P352, P321, P333+P313, P363, and P501|Aggregated GHS information provided by 155 companies from 3 notifications to the ECHA C&L Inventory.|Danger|H317 (81.18%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, and P501|Aggregated GHS information provided by 2191 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere, protect it from all oxidizing materials, and store it at refrigerated temperatures. (NTP, 1992)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Drug Information
For nutritional supplementation and for treating dietary shortage or imbalance.
Alpha Linolenic Acid (ALA) is an 18-carbon polyunsaturated fatty acid with three double bonds. It is also called an omega-3 fatty acid, and is essential for all mammals. Alpha-linolenic acid (or omega 3 fatty acid) intake can decrease the risk of cardiovascular diseases by 1) preventing arrhythmias that can lead to sudden cardiac death, 2) decreasing the risk of thrombosis (blood clot formation) that can lead to heart attack or stroke, 3) decreasing serum triglyceride levels, 4) slowing the growth of atherosclerotic plaque, 5) improving vascular endothelial function, 6) lowering blood pressure slightly, and 7) decreasing inflammation. ALA deficiencies can lead to visual problems and sensory neuropathy. Scaly and hemorrhagic skin or scalp inflammations may also develop.
Alpha Linolenic Acid or ALA is considered an essential fatty acid because it is required for human health, but cannot be synthesized by humans. It is in fact a plant-derived fatty acid. Humans can synthesize other omega-3 fatty acids from ALA, including eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). EPA is a precursor of the series-3 prostaglandins, the series-5 leukotrienes and the series-3 thromboxanes. These eicosanoids have anti-inflammatory and anti-atherogenic properties. ALA metabolites may also inhibit the production of the pro-inflammatory eicosanoids, prostaglandin E2 (PGE2) and leukotriene B4 (LTB4), as well as the pro-inflammatory cytokines, tumor necrosis factor-alpha (TNF-alpha) and interleukin-1 beta (IL-1 beta). Omega-3 fatty acids like ALA and its byproducts can modulate the expression of a number of genes, including those involved with fatty acid metabolism and inflammation. They regulate gene expression through their effects on the activity of transcription factors including NF-kappa B and members of the peroxisome proliferator-activated receptor (PPAR) family. Incorporation of ALA and its metabolites in cell membranes can affect membrane fluidity and may play a role in anti-inflammatory activity, inhibition of platelet aggregation and possibly in anti-proliferative actions of ALA. ALA is first metabolized by delta6 desaturease into steridonic acid.
SYMPTOMS: Exposure to this compound may cause blurred vision, coughing, abdominal pain, nausea, vomiting, respiratory distress, skin burns and irritation of the skin, eyes and respiratory tract. It may also cause decreased fibrinogen levels and increased platelet adhesiveness. ACUTE/CHRONIC HAZARDS: This compound may cause irritation of the skin, eyes and respiratory tract. It may be harmful by inhalation, ingestion or skin absorption. When heated to decomposition it may emit toxic fumes of carbon monoxide and carbon dioxide. (NTP, 1992)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
alpha Linolenic Acid
Linolenic acid Use and Manufacturing
It is made from linseed oil through hydrolysis and fractionation. It can be separated from the evening primrose seeds (containing 20%-25% oil and fat) according to the conventional method after oil extraction, and 70%-80% linoleic acid and 10%-15% γ-linoleic acid can be separated simultaneously. If treated with Candida rugosa lipase twice, the γ-linoleic acid content can be increased from 22.2% to 59.0%. In modern times, it is produced by microbial fermentation. For example, after three types of culture (Mucor circinelloides) and Mortierella isabellina (using glucose as the carbon source), dried mycelia (which may contain up to 35% oil and fat, including γ-linolenic acid Accounted for more than 18% of the amount of fatty acids), extracted crude oil with hexane, and then refined by the general method. In order to prevent its oxidation, the finished product needs to be isolated from sunlight and air, sealed in a nitrogen-filled package and stored at low temperature. It is best to encapsulate it directly in soft capsules.
An essential fatty acid. Occurs as the glyceride in most drying oils. Nutrient. Nutritional supplements. Γ-linolenic acid is an essential fatty acid for human body. As a nutritional fortifier, my country stipulates that it can be used to fortify γ-linolenic acid beverages, blended oils, milk and dairy products, with a usage amount of 2% to 5%. Used in medicine and biochemical research.
Agricultural chemicals (non-pesticidal)|Adhesives and sealant chemicals
Arts, crafts, and hobby materials|Paints and coatings
1,000,000 - 10,000,000 lb
All other basic organic chemical manufacturing|9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)-: ACTIVE|Paint and coating manufacturing|Fatty acids, linseed-oil: ACTIVE
EPA Safer Chemical Functional Use Classes -> Surfactants|Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern|Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]|Cosmetics -> Antistatic; Cleansing; Emollient; Emulsifying; Hair conditioning; Skin conditioning; Surfactant
Computed Properties
Molecular Weight:278.4
XLogP3:5.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:13
Exact Mass:278.224580195
Monoisotopic Mass:278.224580195
Topological Polar Surface Area:37.3
Heavy Atom Count:20
Complexity:301
Defined Bond Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Extract the name, type (main ingredient or excipient), content, unit, and pharmacological action of the raw material from the above information
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