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Linolenic Acid

HCID 178745898
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
949900-18-9
Standard-SMILES
CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)O
InChIKey
DTOSIQBPPRVQHS-PDBXOOCHSA-N
Summenformel
C18H30O2
Durchschnittliche Molmasse
278,4 g/mol

Überblick

Linolenic acid is a clear colorless liquid. (NTP, 1992)

Namen und Bezeichner

Bevorzugter Name
Linolenic Acid
IUPAC
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
Englischer Name
alpha-Linoleic acid
Summenformel
C18H30O2
Molmasse
278.4296

Namen und Synonyme

linolenic acidalpha-Linolenic acid463-40-1(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid(Z,Z,Z)-9,12,15-Octadecatrienoic acidcis,cis,cis-9,12,15-Octadecatrienoic acidall-cis-9,12,15-Octadecatrienoic acidalpha Linolenic Acid9-cis,12-cis,15-cis-Octadecatrienoic acid9,12,15-Octadecatrienoic acid, (Z,Z,Z)-(9,12,15)-linolenic acidDTXSID7025506
Weitere Namen anzeigen
Ai3-111329Z,12Z-Linoleic acid9-cis,12-cis-Linoleic acid
(9Z,12Z,15Z)-Octadecatrienoic acid9Z,12Z,15Z-Octadecatrienoic acidLinolenic acid, crude(Z,Z,Z)-Octadeca-9,12,15-trienoic acidKortacid 1499cis-delta9,12,15-Octadecatrienoic acidPrifrac 2942cis-Delta(9,12,15)-octadecatrienoic acid

Datenbank-Bezeichner

CAS
949900-18-9
ChEMBL
CHEMBL8739
ChEBI
CHEBI:27432
UNII
0RBV727H71
EC Number
207-334-8
Nikkaji
J5.773H

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,9
Polarare Oberfläche (TPSA)
37,3 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
13
Schwere Atome
20
Formalladung
0
Komplexität
301

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Fatty Acids and Fats
DrugsPharmaceuticals -> Listed in ZINC15
Lipids · 2 Einträge

Lipids -> Unambiguous Lipids

Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]

Cosmetics · 2 Einträge

Cosmetic ingredients (Linolenic Acid) -> CIR (Cosmetic Ingredient Review)

Antistatic; Skin conditioning; Surfactant; Emollient; Cleansing; Hair conditioning

SpringerMaterials PropertiesChemical diffusion
FragrancesFragrance Ingredient (Linolenic acid) -> IFRA transparency List
LogP · 2 Einträge

6.46

6.46

Density0.9164 at 68 °F (NTP, 1992) - Less dense than water; will float
Solubilityless than 1 mg/mL at 72 °F (NTP, 1992)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 87.2% (2010 of 2305) of all reports.

Warning

H317 (10.4%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2305 reports by companies from 9 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: 9,12,15-Octadecatrienoic acid, (Z,Z,Z)-

9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 9,12,15-Octadecatrienoic acid, (Z,Z,Z)-: Human health tier I assessment
Fire HazardsThis chemical is probably combustible. (NTP, 1992)
Health Hazards · 1 Eintrag

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.

Hazards SummaryOxidized by air forming peroxides that may spontaneously combust; [CAMEO] Safe when used as a flavoring agent in food; [JECFA] May cause irritation; [Sigma-Aldrich MSDS]

Chemie und Industrie

Pharmakologische Informationen

Pharmacodynamics · 1 Eintrag

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.

Mechanism of Action · 1 Eintrag

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.

Tissue LocationsAdipose Tissue
Cellular LocationsCytoplasm

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
Flash Pointgreater than 235 °F (NTP, 1992)
Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point446 °F at 17 mmHg (NTP, 1992)
Reactive GroupAcids, Carboxylic
EPA Safer ChemicalChemical: Linolenic acid
Reactivity AlertsPeroxidizable Compound
Reactivity ProfileLINOLENIC ACID is incompatible with bases, oxidizing agents and reducing agents. Also incompatible with peroxides, oxygen and water. (NTP, 1992)
Air and Water ReactionsOxidizes in air to form peroxides, which spontaneously ignite. Insoluble in water. Sensitive to heat and moisture.
Hazard Classes and CategoriesSkin Sens. 1 (10.4%)

Sicherheit und Schutzausrüstung

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 Eintrag

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.

Nonfire Spill Response · 1 Eintrag

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.

Personal Protective Equipment (PPE) · 1 Eintrag

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)

Toxikologische Informationen

Toxicity Summary · 3 Einträge

The CIR Expert Panel concluded that the following ingredients are safe in the present practices of use andconcentration described in the safety assessment when formulated to be non-irritating and non-sensitizing, which may be basedon a QRA...Linolenic Acid...

Safe for use in cosmetics, with qualifications

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.

Carcinogen ClassificationNot listed by IARC.
Metabolite Pathwaysalpha-Linolenic acid metabolism

Verwendung und Herstellung

Uses · 4 Einträge

CIR ingredient: Linolenic Acid

Essential fatty acid; Found in most drying oils; Used as a nutrient; [Merck Index] Used in biochemical research, drying oils, and cosmetics; [NTP]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

For nutritional supplementation and for treating dietary shortage or imbalance.

U.S. Production2023: 1,000,000 - <5,000,000 lb
Consumer UsesSoil amendments (fertilizers)
Industry UsesBinder
Household ProductsInformation on 17 consumer products that contain Linolenic acid in the following categories is provided:
Use Classification · 4 Einträge

EPA Safer Chemical Functional Use Classes -> Surfactants

Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern

Fragrance Ingredients

Cosmetics -> Antistatic; Skin conditioning; Surfactant; Emollient; Cleansing; Hair conditioning

General Manufacturing Information · 2 Einträge

Plastics Product Manufacturing

9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)-: ACTIVE